The Trailside Inn

, from answering all of my questions, to asking us questions we hadn’t even thought of, to communicating directly with so many vendors. Every vendor we chose only had incredible things to say about them, and it is clear why. Not only are they organized and professional, but they care about you and making your wedding perfect. All of our guests are still talking about how incredible the weekend was and how much they loved Trailside. As a bride who had trouble delegating, my stress and anxiety melted away the minute we got to Trailside for the weekend. Josh and Ann made everything so simple and easy for us and handled every issue and detail and the weekend was perfect because of that. It is clear how much Josh and Ann care about what they do and the people they work with. They go above and beyond and exceeded all expectations. We are so grateful to them for everything they did throughout the process but especially for our wedding weekend. Trailside will always have a special place in our hearts!

ake sure everything was set up exactly as we envisioned and ensured everything went smoothly for our wedding. We truly couldn’t have asked for better people to support us through our wedding weekend! Josh and Ann were there with us through the entire planning process, offering their professional advice and making sure all the necessary details were given the attention needed. 

was to not have to worry about transportation between events. The owners, Josh and Ann, were incredibly helpful with managing vendors and implementing our vision for the weekend. They have been doing weddings for many years at this point (we were their 100th wedding!) and it shows. They have personal relationships with the local vendors and know all the potential hiccups that we never would have thought of on our own. We would 100% choose them again!

sponsible for how smoothly the day of logistics ran. Their staff was kind and helpful at every turn during the weekend and made everything feel so easy. To be able to spend an entire weekend celebrating with friends and family was a gift and the Trailside Inn made that possible. The property is stunning and makes for a magical backdrop for your big day.

one place - we received rave reviews from our guests.

ed vendor list was amazing, and we had many guests telling us that the food both nights was the best they had ever had at a wedding. We will be encouraging all of our friends to get married at Trailside. It was truly the best weekend of our lives and better then anything we could have imagined.

hey helped to ensure our vision came to life, and we couldn't be more thankful! All of our guests raved about the inn, the florals, the food, and about the overall weekend experience. We felt so well taken care of, and it truly made the day and weekend stress-free and enjoyable for us. Would absolutely recommend The Trailside Inn to anyone looking for a magical weekend experience!

d been friends forever. Our wedding was the most perfect weekend we could have ever imagined. If you are looking for a gorgeous location for your friends and family to spend a wedding weekend there can’t be many places better than Trailside. Can’t recommend them enough, 10/10!

nt 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.

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!!!!

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.❤️

new 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!

ation, 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!

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!

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!!

et 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.

nn 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!

her 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!

s 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!

he 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.

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.

or 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.

on 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!

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.

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!

repared 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!

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 highly recommend anyone to stay at trailside for their wedding !! You won’t be disappointed

en 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.

e 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.

or 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.

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!

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!

ou are looking for a great place to host friends and family for a stress-free wedding weekend.

ith 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!

r 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.

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

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

nding 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.

was amazing and the friendliness of the staff is so much better than other places we have visited.

o 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!

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!