The Trailside Inn

We’re still on cloud nine after having our wedding at The Trailside Inn. It’s hard to put into words just how incredible the whole experience was. Tucked away in the stunning Vermont countryside, this place is pure magic. The views—mountains, lush woods, and a charming babbling brook—were the perfect backdrop for our ceremony and photos. So many of our guests said they couldn’t get over how peaceful and beautiful everything felt. But what really makes The Trailside Inn stand out are the people running it. They aren’t just great at what they do—they’re genuinely kind and down-to-earth. From day one, they made us feel like family. They helped us with every little detail, offered great advice when we needed it, and were always there with a smile and a sense of calm. It was clear that they really cared about making our day special, not just as a job but because they wanted to see us happy. The whole weekend felt like a getaway for everyone. Having the inn to ourselves made it all the more special. The rooms are cozy and comfortable, and we loved gathering around the fire pit at night with our closest friends and family. It was exactly the laid-back, intimate vibe we were hoping for. If you’re looking for a wedding venue that’s beautiful, welcoming, and feels like a hidden gem, The Trailside Inn is it. We couldn’t have asked for a better place or better people to share our wedding day with. We’ll be treasuring these memories for a long, long time.

There is no way I am going to fit enough positive things to say about the Trailside Inn in this box! When we began wedding planning, my dream was to find something that felt like a summer camp, with all my loved ones in one place, but I also wanted it to feel like an upscale cocktail party for our celebration. Trailside accomplished all that and more! Working with Josh and Ann throughout the planning process was seamless -- it was so straightforward. They are so kind, thorough, and run everything smoothly and confidently. Any tiny thing that we worried about, they had solutions for. An amazing part of working with Josh and Ann is that they both had local vendors in mind for our events (who were equally incredible), and for other ideas we wanted to add on, they were super supportive about making any of our outside of their template ideas work perfectly. There is not a single thing about this venue that I would change -- we loved every MINUTE of our wedding weekend, I just wish we could do it ten more times! If you're considering this venue, run, do not walk, to book it!!!!

My daughter’s wedding was held this past weekend at the Trailside Inn. My daughter wanted a space where all of her guests could stay for a wedding weekend. It was perfect, we were able to enjoy a welcome party, the wedding and a Sunday breakfast all in the same idyllic spot in Vermont. The Trailside hosts Josh and Ann were absolutely incredible in every way in helping support our family on this beautiful weekend. They were calm and low-key and helped transition some of our events due to rain. I can’t say enough about how wonderful they were to work with and what a nice place the Trailside Inn was to spend the most amazing weekend in my daughters life.❤️

We had our wedding here in August and could not have had a more wonderful experience. From the second we visited the Trailside Inn to see if it was a good fit for our wedding, we knew we were in good hands. Josh and Ann were superb to work with: responsive, organized, informative, compassionate, and so helpful. They're both wonderful hosts and wonderful people. The venue itself is also a gem. The photos on their website and blog speak for themselves and we appreciated how we maintained the whole property was. If you're considering the Trailside Inn, DO IT!

Working with Josh and Ann was such a pleasure, my husband and I could not recommend to me enough. As someone who works in events I could not have asked for better planning, organization, coordination and accommodations from both Josh and Ann! Not to mention Trailside inn and the entire property is breathtaking - our wedding was everything we hoped for and more! We plan to visit Trailside Inn as a tradition and hope one of our friends or family member’s gets married there one day as well!

Ann and Josh are the most amazing people to work with. They are so kind, responsive, and helpful during the entire wedding planning process. It can feel overwhelming when you start to plan a wedding and not know where to begin. Ann and Josh had a ton of recommended vendors and wedding weekend timelines that were the perfect starting place and guided us through the entire process. Not to mention they were always available to answer questions (and there were a lot!). The inn itself is so beautiful. The grounds are amazing and we were so happy to have the inn full with our friends and family all weekend long. Having the inn reserved for all our guests made it so much easier to spend time with each person throughout the weekend. It was heartwarming to see everyone in the great room mingling and chatting. The fact that the welcome party, ceremony, reception, and after party took place at the same location also made it super easy for everyone and gave people time to explore the beautiful town of Killington throughout the weekend. All of our guests felt relaxed and happy to not need to rush around from place to place for the various wedding activities. Having our wedding at the Trailside Inn was the best decision we made. We are so grateful to Ann and Josh for all of their help and we will be returning there for years to come. We would recommend this venue to anyone!

The absolute best wedding venue we could have asked for!! Josh & Ann are the most helpful & kind people that truly want you to have an amazing wedding and work with you so closely to make that happen! They were open to everything and helped me with things I had not even thought of. I highly recommend them to any and all couples looking for an adorable mountain inn!!

The Trailside was the perfect wedding venue for us and our guests. It was amazing to have the entire place for our friends and family for the weekend and allowed people to really get to know each other. Josh and Ann were incredibly organized and helpful throughout the entire planning process and the day of the wedding, which allowed myself and my *husband* to focus on each other and the day.

Trailside Inn is where it's at for a wedding venue! Josh and Ann are much loved by couples and the vendors they work with. When you book Trailside you get private access to the Inn for an entire weekend of your wedding. Because you have the place all to yourself you can throw a Welcome Party Friday night so you can spend quality time with your guests. The weekend affair reduces so much stress on the day of your wedding so you can actually enjoy your reception since you have spent so much time with the majority of your guests already. The planning process is made super simple because of all of Josh and Ann's hard work. They help walk you through the logistics of your weekend, help introduce you to their preferred vendors, and coordinate all of the behind the scenes action the entirety of the weekend. They are super chill, transparent and get the job done. We love them!

The Trailside Inn is absolutely beautiful. We loved the laid back atmosphere. We specifically chose this venue so all of our friends and family could enjoy the views & be all together under one roof. Josh & Ann are absolutely wonderful. They helped with everything & we couldn’t be more grateful. They responded to emails quickly & kept in touch the entire time we were planning our wedding. I highly recommend having your wedding at The Trailside Inn. It was completely stress free & they did an amazing job with absolutely everything. Thank you again!

First of all Josh and Ann are amazing; professional and just experts at what they do. It rained buckets on our wedding day and they made it so I didn't even care. The Inn itself is charming and all the work they have put into it is of high quality and beautiful. They really have a special place that creates such a fun but intimate setting for your special day. Get married here! You won't regret it!

Josh and Ann are the most amazing hosts. Everything about trailside is incredible. The entire wedding was smooth and amazing because Josh and Ann (owners) are there every step of the way. They communicate, they help, and their amazing space was the talk of the wedding. We got so so many compliments on how things looked, the rooms, the feel, and the accommodations. I cannot recommend them enough. I was a needy & picky bride and they took it all in stride and made my weekend dreams come true.

10/10, A+, perfect score, top marks, call it whatever you want, the bottom line is this place was the best. Our guests couldn't believe we had the whole property to ourselves for the whole weekend. Josh and Ann were the perfect hosts, it was clear they had put on weddings many times before and were always one step ahead. They diffuse the stressful part of planning a wedding and allow the bride and groom to focus on the joy and celebration of the event. We were so well taken care of from the moment we signed the contract at Trailside. There is lots to do in the area, and the venue kept everyone entertained late into the night. If I were you I would stop looking anywhere else and just hope Trailside is still open for the weekend you want.

My experience with Trailside Inn was so delightful, I'm not even sure how to start describing it. In the summer of 2021 my (then) fiancé and I were somewhat frantically searching for a wedding venue. We wanted a place where we would be able to host most if not all of our family and friends because the most important thing was that we were able to relax and connect with our guests. It was on a rainy July day when we drove RT 100 to the Trailside Inn to meet with Josh and Ann. Even in with the dreary weather, the Inn stood out. Nestled in the woods, just down the road from Killington it had the perfect mix of Vermont beauty and solitude. The interior of the inn has been lovingly cared for by Josh and Ann and manages to be effortlessly cool. And then there was Josh and Ann themselves. They are so down to earth but obviously very capable and organized. We knew they would be a huge asset when it came to planning. And honestly, it lived up to our wildest dreams. Josh and Ann are super stars. They were so helpful every step of the way. Whether it was contacting a vendor or answering a question about "how is X typically done" I felt so confident that we had things under control because of them. The weekend itself was, if possible, even more relaxing. When we arrived on Thursday we unloaded food and decor and they just took it all and I didn't have to worry about it again. It left us so much more time to relax and be present. The inn itself was so perfectly charming. We were very fortunate with the weather and got to explore some of the local area but we also enjoyed hanging out in the common rooms for breakfast, after dinner games, and general socializing. We wanted together time, and we got it. If I were to do it over, I would get married at Trailside every time.

We recently hosted our wedding at The Trailside Inn on 8/27 and I will recommend this venue to everyone and anyone I can. It's everything you could ask for when booking a destination wedding. Trailside is located close to so many hiking trails and quiet little Vermont towns. It has the amazing convenience of on-site lodging and you get the whole venue for a weekend making for such a special experience. From start to finish, the innkeepers, Ann and Josh, went above and beyond. They come with recommendations for every part of the weekend and are always available and responsive to questions. They helped communicate with vendors leading up to the wedding and made sure the whole wedding day went smoothly. Our guests raved about how fun the weekend was (and even how comfy the beds are). Ann and Josh help take so much stress out of the planning process. I can confidently say choosing The Trailside Inn was the easiest decision in our whole wedding planning process. I'm really hoping one of our guests will decide to host their wedding there so we can experience another Trailside event!

Trailside Inn was the perfect place for us to have our wedding and our wedding was beyond anything that we could have imagined. Josh and Ann sell the idea of a wedding weekend, and we got just that. Three full days spent alongside our family and friends and it was truly a magical experience. Our dream wedding was to get married in Vermont, and spend the weekend alongside our family and most of our guest list. Around 85% of the guests ended up staying at Trailside with us. It gave us significantly more time with all of our guests and also allowed the guests to meet and get to know each other, which made our wedding weekend even that much more special. Trailside also allows guests to check in on Thursday night, which close to half of our guests chose to do, allowing us even more time to spend with our family and friends, while also allowing our guests the opportunity to explore Vermont and sightsee without having to feel rushed to get back for wedding events. According to the guests, the overwhelming sentiment about the room accommodations were great. The rooms were the perfect mix of Vermont rustic charm, all while having the necessities to make a cozy weekend away. We didn’t have any issues with our lodging whatsoever, in large part due to the owners of Trailside, Josh & Ann. They were on top of everything. We booked Trailside about 14 months before our wedding date. From the initial meeting before we booked Trailside for our wedding, all the way through the end of our wedding weekend, Josh & Ann were extremely helpful and easy to work with. They know all the right questions to ask to make sure your day is what you want, and were also able to help us work through some nontraditional components to make sure everything ran smoothly. They know what they are doing and have their operation extremely dialed. We chose from a list of vendors they had previously worked with, and all of them were phenomenal. They have good working relationships with some truly great vendors, who just like Trailside have an extremely dialed operation. If they are available, we highly recommended sticking to the "Recommended Vendors" list as much as possible, because their prior experience at Trailside made our weekend run seamless. We highly recommend booking Trailside Inn for a wedding venue. Our weekend was perfect and we attribute most of that to Josh and Ann and Trailside Inn.

If you are in doubt at all, book now! You will not regret it! Ann and Josh are incredible hosts and absolute wizards at helping you organize vendors and plan wedding details. The site is beautiful and all the guests are still raving about how much fun they had over the wedding weekend. The game room was a big hit and Josh and Ann helped us with all our personalized touches, like photos over the fireplace and homemade décor for the ceremony. The Trailside Inn was the perfect spot for our dream wedding and we could not have asked for a better weekend!

We just had our wedding at the Trailside Inn, and Ann and Josh were absolutely amazing. They’re LGBT friendly and made us feel welcome from the very first conversation. They were prepared for everything and anything, and helped us through every step of preparing for our big day! Their inn was located between both of our families and we loved the idea of having everyone in one location for the weekend. They have a list of vendors who they have vetted and know will do a great job. (Go with the taco truck!) The vibe at The Trailside Inn is amazing. Ann and Josh make you feel like a friend and they are there all weekend to ensure you are enjoying yourself and not stressing. Even our friends and family couldn’t stop saying how great the location, Josh & Ann, and the weekend were. If you’re looking for a place where you can relax and spend time with those you love most, then this is the place for you!

If you are considering booking The Trailside Inn for your wedding - DO IT. Josh and Ann, and their family, are truly wonderful people who went above and beyond to help us have the wedding day of our dreams. The Inn has gotten some major updates in the past few years (AC in rooms, new bathrooms, solar power) and was a comfortable spot to host almost all of our wedding guests for the weekend. We loved being able to spend as much time as possible with our guests and not need to worry about transportation or any other logistics like that. As for the planning process, Josh and Ann were immensely helpful - quick to respond to emails or even jump on the phone when needed. They know the industry and most area vendors well so it was really invaluable to be able to lean on them when we had questions or concerns. Our wedding at Trailside was beyond anything we could have imagined and we are so grateful!

I had my wedding weekend at trailside inn , Anne and Josh were the best help and most welcoming for all our guests for the weekend ! The venue was clean and very nice and spacious ! I highly recommend anyone to stay at trailside for their wedding !! You won’t be disappointed

What a magical weekend made even better by the Innkeepers Ann and Josh. Our guests were absolutely thrilled to have the whole inn to ourselves to reconnect with those we haven’t seen in a while. Ann and Josh took care of everything and enabled me to sit back, relax, and truly enjoy the weekend with family and friends. The best wedding weekend I could’ve ever imagined.

Ann and Josh at the Trailside Inn are fantastic. We wanted a smaller wedding where all of our guests were able to stay on site for our weekend to all be together. Our wedding at the Trailside Inn captured our vision and more! Ann and Josh worked closely with us throughout our entire planning phase. They were unbelievably helpful by recommending and continuing contact with other vendors. Ever since we signed our contract to the day after our wedding, I truly felt that Ann and Josh had our wedding vision at heart.

We are so, so happy we found Trailside Inn. We hosted a cross-border wedding (half Canadian/ half American from all over) and having the weekend, along with use of the entire Inn for our guests, was a great way to break the ice and have people get together in a relaxing atmosphere. So many people said it was the best wedding they had been to and really enjoyed the venue. There are activities for everyone to enjoy in Killington (great shopping, food, hiking, golf, swimming, etc.) and all of the recommended vendors are top notch and run like a well-oiled machine. We used VT Farms Catering (a must!), Celebration rentals, Linen Shop, and Caja Madera. Josh and Ann were super helpful and supportive throughout the whole process and kept us sane! We had to postpone our original 2021 date because of COVID and they were very accommodating. If I could do it all over again I wouldn’t change a single thing about our wedding here.

BOOK THIS VENUE! My husband and I got married at The Trailside Inn this past weekend and could not be happier with how everything went. The inn itself is the perfect setting for a weekend destination getaway. The surrounding area is gorgeous, with waterfalls and scenic hiking right down the street. The rooms are all beautifully updated with new bathrooms and hardwood. The lodge, downstairs game room and backyard with fire pit are fantastic spots to congregate with guests. The atmosphere is relaxed and inviting, and we received SO many compliments about everything from our guests. In addition to the beautiful setting, the owners, Josh and Ann, were amazing throughout the entire process. They were incredibly organized and professional. They had google sheets and questionnaires and would remind us about deadlines and timelines in a way that made everything a breeze as far as planning goes. We went with all their recommended vendors and were not disappointed. They clearly love what they do and it shows. In choosing The Trailside Inn, you will not only get the best wedding planning duo ever, but you will feel like you've gained some true friends. Josh joined in on some lawn games with our guests and Ann seamlessly walked us through all of the finer details of the weekend while easing our nerves. My husband was deployed for much of the pre-wedding planning and I can personally say I am forever grateful to both Josh and Ann for not only making everything easier but fun at the same time. I cannot imagine having our wedding anywhere else. If you are fortunate enough to find them free, book without delay!

We booked The Trailside Inn in early 2021 amidst high market demand for wedding venues on popular dates. Josh, one of the innkeepers, was very flexible in offering us a video tour of the lodge via FaceTime, and answered all our questions with complete honesty and transparency. We made two planning visits between booking and our wedding, during which Josh and Ann (Josh's wife, co-innkeeper, and lead event coordinator), helped us turn our concepts and ideas into concrete plans. They provided vendor recommendations, guidance on ceremony and reception processes, and valuable insight based on their years of experience. Overall, the booking and planning process could not have been easier with the help of Josh and Ann. On wedding weekend, things were even better. The Trailside is a family owned and operated business, and the nature of the venue means it will be just your friends and family on the property throughout your event. As a result, Josh and Ann are able to provide unbeatable personal attention and detailed service. Ann is also an outstanding event coordinator--once you work out your contract details with individual vendors, Ann handles all further correspondence and operational planning for setup, execution, and takedown. The ultimate consequence of this level of attention and service is that once you show up, you can enjoy your time with your friends and family rather than worrying about putting on a big party. Importantly, Josh and Ann are also very familiar with all the other vendors you'll need. Because the Trailside's main business is the provision the party space and lodging (and because tourism/hospitality are some of Vermont's top industries), things like food, flowers, music, and tables/chairs/place settings all come from separate vendors. Although this can be a lot to manage in the beginning, Josh and Ann have great working and personal relationships with nearly every vendor in the area, and can provide a direct line to whoever you need, even if you're having trouble getting in touch. This is an invaluable asset that reduces the stress of managing several contacts at once. Further, the nature of this arrangement means you have 100% complete customizability in how things look, sound, feel, and go throughout the weekend. Want to ride bicycles down the aisle? They've done it, and know a photographer that will make it look like the cover of a Nicholas Sparks novel. Want a Celtic harpist to play Lord of the Rings melodies as you marry in the woods? Not a problem. At the Trailside, you're not limited to the standardized "packages" that a lot of all-inclusive venues offer, and although it's more work, it's very much worth it. One of the most unique parts of the Trailside experience is having the entire property to yourself for an entire weekend. Josh and Ann help you organize and execute a "welcome party" on the day before your wedding so guests can get in, get fed, and get to know each other more casually before reconvening the next day for the big event. This pays off immensely in creating familiarity between guests so that when dancing time comes, nobody is bashful. I'm fairly certain every single guest we had on our weekend commented not only on how beautiful the property was, but how great it was that the whole weekend was just our group. Ultimately, if you decide you want to (or are told by your families that you have to) engage with the wedding industrial complex, there is no better way to do it than the Trailside way!

Trailside was everything we could have wanted in a venue, and more! Our guests were so impressed with the location and how friendly the staff was. I highly recommend Trailside if you are looking for a great place to host friends and family for a stress-free wedding weekend.

I really can't think of anything the folks at The Trailside Inn could do to improve the wedding experience here. Ann and Josh were flexible, helpful, and great at communicating with us through a pandemic. We started planning our wedding in 2019 and like many others were not able to hold our wedding in 2020 but did have our party in 2021. Ann and Josh made the initial planning low stress and easy to navigate and managed to keep that vibe through to our wedding day itself. In short, they're incredibly easy to work with and very helpful. The venue is beautiful and awesome! The recent renovations to guest rooms and the game room turned out really well. The whole place has a rustic/hip (still modern and super clean) vibe. Our wedding took place at the beginning of October and the outdoor area where the ceremony was set up could not have worked out better. It's a really cool spot! Our families aren't from VT so an additional advantage to having our wedding at Trailside for the weekend was that our guests had the chance to explore the area. So, they all made the trip up for our wedding of course, but most guests turned the trip into even more of a weekend getaway than we planned it to be (which we all definitely needed after being locked down for so long). In short, the people are knowledgeable and helpful and the place is beautiful and fun!

There aren't enough amazing things to say about Trailside! Josh and Ann helped us navigate a mini-mony in the thick of COVID 2020, while never losing track of our plans for a bigger reception in 2021 with all our friends and family. Their support and knowledge was invaluable and we loved working with them. On top of that, Trailside was our dream wedding venue through and through. Housing on site for all friends and family, beautiful rustic woodland backdrop, phenomenal vendors and relationships, opportunities to DIY and think out of the box, and so much more! We can't recommend Trailside enough and can't wait to keep visiting for years to come.

When COVID ruined our destination wedding plans we were so upset! Little did we know it was the best thing to happen! Finding the Trailside Inn, and as a result Josh and Ann, truly was the most amazing thing that could have happened. We couldn’t have asked for a more perfect wedding! They were responsive and helpful from the first phone call, through the countless ( my wife might say obsessive amount) of emails I sent, right through our fairwell brunch! They had the best advice, you could tell they have done this many times. The Inn itself is beautiful and cozy and is big enough for all your guests. Our guests felt right at home, they even sat in the great room in their robe drinking coffee watching the sun rise! The game room was a perfect addition for the welcome party and the after party! The best part about having our wedding there was it was affordable and it was a whole weekend! We went up Thursday night with our bridal party and had full access to the place just for us. We decorated and spent time with those who helped make our day special. Friday we had the welcome party with Caja Madera taco truck (highly recommend) with all of our guests which gave us the time to mingle and connect with everyone! Many people say their wedding went by so fast and they didn’t get to talk to their guest as much as they liked, but I don’t feel that way at all. That’s because you have a whole weekend to spend time with everyone! Our planning meetings were over zoom because of covid but that didn’t make it any less personable and we didn’t feel like we missed out at all. That’s the kind of people Josh and Ann are, they make you feel like you’ve been friends for years and make you feel so comfortable. They took all the stress out of planning! The organization made us feel so calm and stress free throughout the whole process. The day of the wedding, Josh and Ann had everything covered, all I had to worry about was saying the right name at the arbor! (I did) My best advice is to book your wedding here, trust Josh and Ann on their vendor recommendations and you will have a weekend you will never forget. We have been told by so many that our wedding was the best wedding they went to and I know for a fact it is because we had it at the Trailside Inn! All the vendors we used listed below are highly recommended and were all suggested by Josh and Ann! Welcome party- caja madera taco truck Caterer- Vermont farms (best food ever!) Linen- the linen shop Dj- Vermont DJ Rentals- rain or shine Floral- Pittsfield garden center

Wow! Trailside Inn offered everything we could have ever imagined in our wedding weekend and more! Josh and Ann, the owners of the Inn and the day-of wedding coordinators are total rock stars at what they do. As you plan your wedding, they will be by your side the whole way recommending vendors and fitting all of the details together. Then during the weekend, they make sure EVERYTHING happens without a hitch. They are so welcoming to all of the guests and make sure to be on a first name basis with all parents, aunts, uncles, and grandparents. Our guests raved about them and how well they complement their cozy, ski-themed inn! Unique wedding features that come with Trailside (most of which we didn’t even know we wanted until we saw them) include the Friday night welcome gathering for all guests to catch up and get to know new people, the Barn and Loft apartments for the wedding parties to stay in, the beautiful wooden altar for the ceremony, the tent on site for dinner and the party (!), and the game room in the basement for the after party! Trailside truly far exceeded our expectations and made our special weekend as perfect as we ever could have imagined. We cannot thank Josh and Ann enough! We 1,000% recommend Trailside for your wedding and can’t wait to get back this winter to ski Killington/Pico and relive our incredible memories! -Jeff and Kristina 8/28/21

I wish we could relive our wedding weekend! The Trailside Inn is a beautiful hidden oasis in Killington VT. Josh and Ann were so helpful from the start and were incredibly understanding and accommodating when we rescheduled our wedding because of the pandemic. The whole weekend went so smoothly thanks to Josh and Ann’s oversight and expertise. We loved being able to spend time with our guests all weekend. The Friday night welcome party allowed us to truly enjoy the reception, since we had already talked to all of our guests the night before. The day of the wedding was truly a breeze and so memorable. Our guests could not say enough about the venue, the food (Caja Madera and VT Farms Catering!), the music, the flowers. The game room was a great place for the after party for guests staying on site and that was a huge hit. My husband and I had a blast, and so did our guests! We also were able to include our dog Guinness in our weekend festivities, which we were so happy about (and he loved the attention)! Thank you again for a truly amazing weekend! I would highly recommend to any couple considering this venue.

The Trailside Inn is owned and operated by two amazing people who literally work hard to ensure everyone is comfortable and cared for. We enjoyed the grounds, thought the facility was amazing and the friendliness of the staff is so much better than other places we have visited.

I went to my sisters wedding at Trailside and it was the most beautiful wedding I have ever been to. Being able to spend the whole weekend with family and friends was a great way to celebrate the marriage. Josh and Ann were helpful and so organized. They know what they’re doing and will make sure you have a perfect event. I will always have amazing memories from this weekend. I’m just jealous my sister found this perfect venue before I did!

We had our wedding at the Trailside Inn and it was an amazing spot to have a wedding. It was intimate and rustic with great spaces inside and out for our guests. Josh and Ann were so pleasant and personable to work with. We loved the venue and would recommend to anyone looking to have a Vermont wedding. We loved that the majority of our guests could stay on site and celebrate all weekend!

From the very first steps of walking onto the property at the Trailside Inn, we KNEW this would be our wedding venue. The Trailside Inn has "rustic Vermont" all over it. From the driveway, to the wooden covered interior, to the fire pits, babbling creek, beautiful views, and unbelievable guest rooms. If you are looking for that perfect Vermont experience/getaway wedding, this is the place. The property is surrounded by ample green space for activities and lounging throughout a weekend event. The interior of the venue is tons of exposed wooden beams, wooden tables, and has such a cozy VT vibe. This is what we were looking for. The owners, Josh and Ann, don't consider themselves Wedding Planners, but rather Wedding Guides. They are both there to walk you through every step of the way, but only to ensure you are getting the wedding you deserve, and to ask the questions you may not have even thought about. Their openness to our ideas, and their suggestions (local vendors, caterers, and tips on where to swim, golf, bike, hike, all the fun!) were all discussed enthusiastically, and in a timely manner. We thoroughly appreciated the constant communication with the venue, even if it was the smallest of questions. Even throughout the weekend, Josh and Ann were as hands on or hands off as we wanted, and were both always nearby if we needed anything at all. Josh and Ann are pros at making sure your wedding weekend is what you're looking for. They absolutely know their stuff! Beyond being so knowledgeable on wedding weekend events, Josh and Anna are just some of the nicest people you will ever meet or work with. Our guests loved the feel of a privately, locally owned venue like this, and Josh and Ann are a testament to that. They made sure our guests were taken care of, and we never stopped hearing how much everyone loved both of them. There are also two dedicated spaces, separate from the main venue (but only 10 yards away) which housed our wedding party, the spaces have private bedrooms, full kitchens, a billiard table, and allowed our wedding party to have that “VIP” experience they all deserved. This was AMAZING to have throughout the weekend if anyone just needed to step away from it all for a few minutes, or relax in a private space with close friends. The venue itself is perfect for a relaxing weekend. From the absolutely gorgeous guest rooms (seriously, everyone was SO thrilled with the spaces, beds, and amenities), to the game room (billiards, jenga, music, lounge furniture, private restrooms, beer pong, etc.) which is open for late-night fun. The back deck of the venue was also a treat as our guests were able to enjoy a beverage and food off the grill while being immersed in the surrounding VT wilderness, any time they wanted!. Being able to have your own little getaway for the weekend where all guests stay on site, and the only people on site are your guests, was really such a unique wedding experience. We were really able to make it our own. We were looking for a perfect, and private New England location that housed our guests for an entire weekend, and the Trailside Inn could not have been more perfect. If we had the opportunity to ever get married again, this would be the place. Maybe a 5 year reunion celebration? We're SO in!

We recently got married at the Trailside and we have not stopped smiling since. It has taken us several attempts to find the right words to describe how perfect our wedding weekend at the Trailside was. The environment and atmosphere that innkeepers Ann and Josh have cultivated is one of a kind. If you are even considering the Trailside as a possible venue, legitimately forget all the others and cha cha slide over to the Trailside. The idea of holding a 3-day long celebration with all your loved ones as the only guests in their stunning property is brilliant. From arrival to checkout, Ann and Josh made everything simple, streamlined and actually fun. They have experience in both hospitality and wedding industries, which made us feel like we were treated as human beings rather than just another client. They are so caring and really make you feel like a long time friend. We originally planned our date in 2020 and due to COVID we had to postpone. Josh and Ann always kept us updated on the new state regulations as they came out and they were quick to respond to any questions or requests. When we ultimately had to postpone, they offered a new date in 2021 without hesitation. It was amazing to have such support and to feel like a priority during such a stressful time. They also have a lot of professional connections with amazing vendors. They coordinate the needs of the wedding couple and timing behind the scenes, so we wouldn’t have the stress of planning all the details. Throughout the weekend, we never had to worry about anything because Josh and Ann were on top of it. No detail, no matter how small, was forgotten. From helping us organize decorations, putting our gifts/cards into a box that we could easily put into our car, and resupplying food or wedding favors, they’re like awesome wedding ninjas and we were so busy having fun we didn't even notice it happening. Josh and Ann are also very communicative and easy to talk with via phone, email or video. Since the very first meeting with them, the entire process of pre-wedding planning, day of the wedding coordination, and even after the wedding details, they answered all questions quickly and professionally, and quelled our nerves when we got the jitters. We wish we could leave more than five stars, because the Trailside and its lovely innkeepers deserve so much more than that (like, at least 100 stars). We love you Ann and Josh! Thanks for our dream weekend!

I cannot say enough about our entire wedding weekend with Trailside. Ann and Josh go above and beyond in everything they do, and are so seamless about their work you never even notice what’s happening until this beautiful wedding comes alive in front of you. From sending an email to see if the venue was open and getting a call from Josh twenty minutes later, to debriefing and laughing with josh and Ann after the wedding, they were the most supportive and fun coordinators you could ask for. This wedding was better than anything I could’ve ever asked for. From the beautiful scenic environment, to the low key vibe that allowed everyone to mix and mingle, to the AMAZING vendors like Caja Madera taco truck for the welcome party, to The Linen Shop VT and Raine or Shine Rentals. The highlight was VT Farms Catering and Vermont DJ. We had rain during our wedding day and Ann and Josh pulled together a beautiful ceremony under the tent last minute. It was perfect and everything happened with no stress. Our guests continue to rave about the wedding, saying it was one of the best they’ve ever been to. You plan a wedding for so long, that when it comes together this beautifully you can’t feel anything but grateful, and SO much of that is due to Trailside Inn and Ann and Josh and the stellar team they put together. If you are looking for a beautiful Vermont vibe, wedding coordinators and inn owners who feel like family, and killer food and dancing, you have your spot. My fiancé and I joke that we will be back to Trailside Inn next weekend because it was so perfect there.

It’s hard to even know where to begin when talking about Trailside and the lovely Inn owners, Josh and Ann. Let me start by saying if you are considering having your wedding at Trailside, just do it! We had our wedding there in June of 2021 and it was perfect. We loved the idea of having a weekend long event and it was so wonderful and unique to be able to find a place to do that where our guests would be the only ones on the (absolutely stunning) property. My husband and I had the best weekend - even better than we could have hoped for - and our guests have already started to request that we plan a 5 year anniversary party at Trailside. Josh and Ann are so organized, detail oriented and easy to communicate with - in addition to just being wonderful people! They made every part of the planning process so easy and seamless, even as we dealt with changes due to COVID. Due to the pandemic, we ended up making some pretty significant changes to our plans just a few months out and they could not have been more helpful or supportive during that process. All of the vendors they recommended were equally as great. We had tacos from Caja Madera on Friday night and our reception dinner was done by Black Diamond BBQ with dessert from Dream Makers Bakers. All were recommended to us by Trailside and our guests continue to tell us how amazing the food was (best wedding food they’ve ever had!) :) As we went through the planning process and interacted with different vendors, all of them told us that we were in excellent hands with Josh and Ann and that they absolutely loved working with Trailside. As someone who knew nothing about planning or coordinating a wedding, but who is also very type A and anxious, I can honestly say that I had no anxiety during the wedding weekend because Josh and Ann were on top of anything that came up. From pre-wedding planning to day of coordination, they were truly there for anything and everything we could have wanted or needed. We can not recommend them highly enough!

Not only is the Trailside the most beautiful setting for any wedding celebration, it is owned and run by two of the absolute best folks working in the industry! Josh & Ann are so welcoming and truly go above and beyond to make each wedding special and unique! They've completely transformed the Trailside in just a few years of ownership to be an environmentally conscious, contemporary space without sacrificing the cozy warm feeling you want from an inn in Vermont! They really understand that at the heart of each wedding is the melting of two big families and do an amazing job of hosting folks for weekend long celebrations that bring everyone together. They'll make sure everything goes smoothly on the big day and after the wedding, you'll end up with two longtime friends and I bet you'll be back to celebrate your anniversaries! I'm a wedding photographer based in Burlington, VT, have shot over a hundred weddings in my career, and can say hands down that the Trailside is top of my list of venues!

Josh and Ann somehow managed to make even wedding planning during a pandemic seamless and easy. They were astoundingly responsive and knowledgeable about our options and the VT state regulations throughout our process. We were their only wedding in 2020 and couldn't be happier that we chose that path. Our super small ceremony and mini-reception was amazing on Trailsides beautiful property, and it was very cool to have the whole inn to ourselves with such a small group. Josh and Ann offered help while still giving us space to make everyone feel more comfortable with the current COVID atmosphere. While they were more hands off this year, they were never far away and always available to help if we needed something or had a question. We cannot wait for our bigger planned reception next year with them and what I'm sure will be more visits to Trailside for fun in the future! We also cannot thank Josh and Ann enough for their help and positive attitudes - this year proves that they are willing to help make your wedding dreams happen however they can!

Josh and Ann were extremely helpful and wonderful for the weekend of the wedding! There were signs up about wearing masks in common spaces so everyone could stay safe, and they always had masks on to protect us in return, even though they're pretty safe up in Vermont. In trying to get a champagne toast right before the ceremony set up we had a spill from wind, and they quickly helped us find a container for the champagne so the light glasses wouldn't tip over so we could move along to the ceremony. The whole inn is BEAUTIFUL, and I can't wait to go back next year for the non-pandemic version of the wedding with everyone!

While we ended up having to cancel our wedding at the Trailside Inn due to Covid-19 restrictions, i'd still highly highly recommend them to any couple considering a Vermont weekend wedding! Josh and Ann were amazing to work with. SO supportive, always available to talk on the phone and calm me down, especially during the crazy pandemic planning. They are just the nicest people. Trailside Inn was such a great venue with an excellent game room, beautiful surroundings, and the ability to host most of your wedding on site. We are so sad we were not able to have our wedding there but will definitely visit in the future and hope whoever is reading this will be able to have an awesome wedding weekend there someday after this craziness has passed!

Where to begin?! Choosing the Trailside Inn for our wedding weekend was one of the best decisions we've made. It's a beautiful drive into the Vermont Mountains and the Inn is nestled in right outside of the main "city center" just far enough away that it's peaceful and quiet but not too far away from activities and restaurants in the area. The owners, Josh and Ann are down to earth, wonderfully attentive and awesome people. My husband and I live in Philadelphia and we were a little anxious about how to plan a wedding so far away, but Ann and Josh helped make it flawless and easy. When the weekend of the wedding came, they were there to help us with anything we needed. The best part of having our wedding at Trailside was the fact that you have an entire weekend to spend with your friends and family under one roof, away from the bustle of real life. We were so excited to actually have time to spend with our loved ones, rather than most weddings where the bride and groom basically walk around saying their hello's for the entire night. The energy that we felt from our loved ones that weekend was incredible, and a big part of that goes to how great of a space the Trailside Inn is. There is enough room for everyone to hang out, mingle, relax, or play games without feeling like you're elbow to elbow. Our guests still to this day (5 months later) cannot stop raving about what an amazing weekend it was. Some friends were even joking about coming back next year and having an "anniversary weekend" for us just so they can experience Trailside Inn again. Thank you again Josh and Ann, you guys ROCK! No regerts!! <3

My husband, Colin and I had our wedding at Trailside over the long weekend in October and we could not be happier with our decision! Trailside was the first venue we went to look at after getting engaged and after seeing the Inn and meeting with Josh and Ann, we knew instantly that Trailside was the place for us. We went to a few more places, just to be sure, but by the end of the weekend we had committed to our wedding date. Throughout the entire planning process, Ann and Josh were nothing but amazing! They're recommendations and guidance were spot on and they really supported us in planning a weekend that was truly unique to our vision and style. Going into the process, we were both pretty nervous as neither of us were too keen on large parties or being the center of attention, but Josh told us from the beginning to think about it as a fun weekend with our friends and family and at some point we were just going to get married. It really made us feel at ease and that's exactly what we were able to do. By the time our wedding weekend came around, we felt fully prepared and knew we were in good hands. Both Ann and Josh made sure both us and our guest had everything we needed and ensured that everyone had a truly amazing time. They checked in on us and our families regularly and we got some many compliments from our guest about their experience at Trailside. The vendors they recommended were wonderful and really allowed us to tailor the weekend to our needs. The relationships they've formed with these vendors over the years made for a stress-free experience as everyone was clear on expectations, timelines, and all the (many) details that go into a wedding. Despite our initial reservations when it came to planning a wedding, we had the absolute best time and that had so much to do with Ann and Josh and the beautiful Vermont backdrop that Trailside provides. We can not more highly recommend Trailside and it will always have a special place in our hearts. If a date opens up and you have the chance to hold your own wedding at Trailside TAKE IT IMMEDIATELY. I promise you that you will not regret it.

I don't even know where to begin! Trailside Inn is amazing! My husband and I were married at Trailside in Sept 2019. We started talking with Josh and Ann back in 2017 when we nailed down our date. Throughout the year and a half we had the venue booked, we couldn't have felt more at ease or excited about our decision. Josh and Ann connected us with AMAZING vendors, assisted with all of the coordination and kept us on track with all of the things we needed to do. Josh and Ann are amazing people and welcome couples and their families into their home with open arms and we are so thankful that they do. The ability to house all of our family and friends under one roof for an entire weekend was exactly what we were hoping for our wedding....and with Josh and Ann running point on just about everything, we were able to spend so much time with our guests never felt rushed. This allowed my husband and I to enjoy every moment of our day together. I would highly recommend Trailside for any couple looking for a wedding venue that allows you to spend time with family and friends, work with amazing people, and enjoy the beautiful area of Killington VT.

Trailside Inn is a magnificent venue for making beautiful wedding dreams come true ! No stress or worries with owners Ann and Josh ! They were like having family ..catering and making everything run perfectly With their kindness 👏🌟😘

Josh and Ann were amazing. They made sure we had everything we needed at all times. They dealt with everything from helping decorate to dealing with all of the vendors as needed so we did not have to worry about a thing. They are kind and professional and truly make you feel like your wedding is the top priority. I would highly recommend having your wedding at the trailside.

Everyone says that their wedding was the best day of their lives. That's certainly true, but imagine if all of your guests tell you that your wedding was the best one they had ever BEEN TO! We heard that a lot after our wedding. The Trailside Inn has a lot of special going for it.  First, Josh and Ann, the Innkeepers are magnificent people. It didn't matter that we didn't the foggiest idea about how to plan a wedding. With a little bit of vision, anyone can do it with their help! The one thing that my wife and I said along the way was that they make it feel as if your wedding is the only one that they have to plan for the year. They are prompt, thorough, and really care. Even through some freak-out moments on our end of the planning process, Josh reminded us that as part of the contract, we had a "No freaking out clause" and that everything was going to be fine. Aside from all of that, we feel as if we made friends for life. They're just that cool. Second, the "Wedding Weekend" format is particularly heart warming. Your best friends and family arrive for an outdoor get-together on the eve of your wedding, then spend the wedding day exploring the beautiful Killington area before the ceremony. This really breaks the ice for the whole weekend. By the time the ceremony and reception come around, there is enough comfort and familiarity to dance your tails off and not care who is watching! When the weekend is over (it still goes by fast, believe me) you've reacquainted old friends and family and fostered new friendships.  Third, the recommended vendor list that Josh and Ann have is top-notch. We took their advice on catering, photography, rentals, flowers, favors and makeup. The Killington and surrounding area has a small family feel and everyone is remarkable.  Last, but certainly not least, The Trailside Inn is the perfect place for your wedding. Its combination of rustic elegance meets modern farmhouse make for a cozy feeling for all who attend. The best part about this venue over others is that it's all yours for the weekend.

Where do we even begin?! From the moment we decided to have our wedding at Trailside Inn, Ann and Josh have been the most organized, helpful and detailed coordinators. They made planning a wedding from out of state so simple and seamless from the very first meeting up until the weekend of. All of their suggestions from our amazing catering to florals to welcome party details - s’mores and beer were spot on! On the actual wedding weekend, Ann and Josh were there every moment for us and our guests, but not intrusive at all, helping us put on such a great party! A thunderstorm passed through on our wedding day and we had to change our ceremony and cocktail hour plans but it didn’t matter in the slightest. Ann and Josh took attention to every detail and even moved the beautiful arbor under the tent so we could still get married under it! All our friends and family have been telling us that this was one of the best weddings they have been to and much of that is because of our wonderful hosts at Trailside Inn. If you envision having your wedding in the mountains where the majority of your guests can all stay under the same roof, have a whole weekend of amazing food and drink, games, lovely breakfast, and with the most relaxed vibe you could have on your wedding day, look no further and book at Trailside! You will be in wonderful hands like we were. We can’t thank you enough for helping us plan such an amazing event and we hope that we have made friends for years to come!

Having our wedding at the Trailside Inn was the best choice we ever made for our wedding day. The quality of service from the InnKeepers/Wedding Coordinators, Ann and Josh, made our special day flow and they executed everything seamlessly. Ann and Josh communicated with us throughout the entire year to assist in the planning process, the level of detail they put into the pre-wedding set-up was fantastic and made us feel less stressed for our big weekend. As for the Inn, what an amazing place, the feeling/decor is what captured our attention when we chose the place, and the amount of feedback from our guests reassured us that we choose the right place. We choose the venue based on its location, the decor and the fact you get the entire Inn for the weekend. If you are looking for a great venue that will allow everyone to have a laid back/stress free weekend, then this is place to have the wedding of your dreams. We have recommend this venue to several of our friends and hope to go back to take part in our friends wedding. Thank you Josh and Ann for all the help with vendors, sharing past ideas and making our wedding weekend one to remember forever.

I can't express how very much I loved my daughters wedding. It was a weekend of fun and family and love. Josh and Ann were so warm and welcoming to everyone. They worked so hard to make sure the weekend was perfect. Honestly, it was just amazing . I hope someone else I know gets married at The Trailside Inn!

Had a blast at the Trailside inn this ost weekend. Met so many new friends you felt you knew forever and had so many good laugh with friends who I haven’t seen in forever. Sad it’s over but very pleased with the wedding overall. Staff was super friendly and had everything we needed to have a comfortable stay. Definitely would recommend the Trailside inn. Thank you guys for the good memories #onemoreridgeway

Best weekend of our lives! I cant say enough about how amazing the entire weekend went at Trailside Inn. When you book your wedding at Trailside the entire facility is rented out just to your party for the whole weekend. Everyone says how fast the wedding goes by so having the whole weekend made all the difference and made us feel we could really enjoy every minute with our family. Josh and Ann, the owners of Trailside, are the two most wonderful people. They made us feel at home the second we walked in and they made sure everything ran smoothly with all our vendors, we never worried about a single detail. Every vendor we selected was also based on Trailside's recommendations and we couldn't be happier with our choices. Homer Horowitz-Clove Hitch Photography, Vermont Farms Catering, and Trish at Pittsfield Garden Center, you would be CRAZY not to use these vendors. We gave Trish a very low budget and I couldn't believe how she transformed every inch of our reception, she must have hand picked every flower. We had the best food I've ever had at a wedding and Vermont Farms even catered our after party. The after party was held right on site on the lower floor of Trailside. No shuttles needed, no hotel employees trying to quite down the party, just you and all your family continuing the dancing, singing, and great times! Homer, our photographer, understood everything we were asking for and made it happen. We have the most beautiful, natural, real photos from the wedding. No fake or cheesy forced pictures and he was still able to capture every moment. I want to jump back to Josh and Ann and make sure this review is clear. Josh and Ann are AMAZING! They made sure every detail was handled and we never worried for a moment. They truly care about the people they invite into their home and make you feel like family. If you are still reading this review and want to have the most relaxed, fun, perfect wedding, then you found what your looking for at Trailside Inn.

From the moment we toured the Inn to our final farewell after we said "I DO" Josh and Ann were so welcoming, accommodating, and made our special day more spectacular than we could have ever imagined! They say they are not wedding planners, but the amount of work and effort they put in to coordinating with all of our vendors, creating a timeline of events, sharing ideas of table layouts, and providing supplies that just added that extra touch, made us feel like they were truly invested in making our event spectacular! They are professional, yet welcome you into their space like you are part of the family! Would not hesitate to recommend this venue for any event!