Old Town Trolley Boston

Serving All of Massachusetts and Beyond

Service area

4.9

Verified reviews from real couples

Everything went off without a hitch. Our driver was great, easily navigating the streets of Harvard Square to take our guests from the church to the restaurant reception. Our guests loved the trolley!

Laura C.

5.0

The trolley was great! The driver was very punctual and knew his way around Boston to avoid some traffic. The two things I wish we prepared better for were: 1. No Bluetooth and we didn’t bring an AUX cord and 2. Water was not provided and it was a very hot day. However, I would absolutely rent a trolley again. The pictures came out wonderful and our guests really liked it.

Stephanie F.

5.0

Kimberly

GROUP SALES AND CHARTERS

Typically responds within 24h

AWARD WINNER

Thanks to recommendations from couples on The Knot

Old Town Trolley Tours of Boston is a wedding transport service based in Boston, MA. This company provides a one-of-a-kind chauffeur experience for your special day. You can travel from your ceremony to your reception in a classic trolley vehicle, arriving in comfort and undeniable style. Old Town Trolley Tours has a fleet of over 40 vehicles ready for their clients’ use. These sleek motorcars boast a characteristically vintage style, giving your event some extra flair. The bright red exterior and green-topped roof of the trolley create an eye-catching spectacle, while the wooden seats of its interior evoke old-world whimsy. You can hire Old Town Trolley Tours to coordinate transport on your big day, and they can also be hired for tours around Boston for your wedding shower. This gives you a wonderful opportunity to bond with your entourage prior to your momentous occasion, enjoying the sights of the city. The drivers employed by this company are fully trained, courteous, and safe, ensuring that you reach your destination in total relaxation.

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Details

Transportation

Shuttle Service

Trolley

Wedding Activities

Rehearsals & Parties

Wedding

Awards and Affiliations

2023 'Best of Weddings'

Join couples who chose award-winning vendors for their wedding

Meet the team

Kimberly

Group Sales and Charters

I look forward to working with you to help make transportation a breeze!

4.9

out of 5.0

22 reviews

Your trust is our goal. Our community relies on honest reviews to help you make those big decisions with ease.

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Laura C

Highlighted review.

11/13/2025

Everything went off without a hitch. Our driver was great, easily navigating the streets of Harvard Square to take our guests from the church to the restaurant reception. Our guest...

s loved the trolley!

Stephanie F

7/08/2025

The trolley was great! The driver was very punctual and knew his way around Boston to avoid some traffic. The two things I wish we prepared better for were: 1. No Bluetooth and we...

didn’t bring an AUX cord and 2. Water was not provided and it was a very hot day. However, I would absolutely rent a trolley again. The pictures came out wonderful and our guests really liked it.

Any questions?

Megan B

9/02/2024

We used Old Town Trolley as transportation for the bridal party on the wedding day and it was amazing! Our driver was super knowledgeable and comfortable driving around Boston- he ...

knew the best place to stop so we could take photos and got all 23 of us where we needed to be all day with multiple stops. The trolley was clean and comfortable and had plenty of room for everyone!

Marcy M

4/25/2023

Great experience working with Old Town Trolley for our wedding guest transportation in downtown Boston! The drivers went above and beyond expectations to make the experience fun a...

s we needed to fill a bit of down time between the ceremony and reception. Guests were given an impromptu Boston tour and couldn’t stop raving about their experience. We are so glad we went this unique and charming route for wedding transportation! Can’t speak highly enough of Old Town Trolley!

Pamela F

12/14/2022

We hired Old Town Trolley to transport our wedding guests between the reception (with excellent free parking) and the wedding (Newbury Street in Boston) and back to the reception. ...

Perfect choice. Kim in the office is responsive, professional, thorough, and simply excellent to deal with. All questions were answered quickly, completely and accurately. We had 79 people at the wedding, nearly everyone took the trolley, and our guests had nothing but good things to say about it. Trolleys were clean, fun and efficient. This is the best solution to the problem of transporting wedding guests around Boston.

Gale N

12/06/2022

My son and daughter-in-law hired Old Town Trolley for their wedding this past October. It was a wonderful experience. Our guests loved it!! Right from the beginning discussion w...

ith Karen in the office I knew it was going to be ok. She answered every question, arranged everything that we wanted and was very professional. The driver was terrific -- right on time and extremely accommodating. Even when it got a little chilly at the end of our ride, heat was provided and it was very comfortable. Would highly recommend!!! And, it's a great way to show of of town guests Boston!!

joan a

11/15/2022

Had a great experience. Lots of fun and excitement going to and from the church /venue. Old Town Trolley was responsive when we had an issue with one trolley that had a mechanica...

l problem. Thanks Kim!

Joelle H

11/14/2022

I booked 6 trolleys for 3 hours to bring 250 wedding guests and bridal party to and from the ceremony/venue in Boston. They did a great job keeping to my timeline and getting every...

one to the destination safely, reliably and efficiently. The trolley coordinator was vital to the smoothness of the day. The trolleys also made for a fun ride through the city and photo op for everyone!

Laura R

11/10/2022

The Framingham History Center hired OTTB for our Halloween event, the Haunted Trolley Tour, which required 4 Stadium trolleys to drive across Framingham for 45 minute tours. The tr...

olley drivers were exceptional and working with Kim V. was a breeze. Kim made sure the trolley portion of our event went off without a hitch. We look forward to working with OTTB again soon.

Sandy S

10/24/2022

Sandy Sneeringer Old Town Trolley was awesome! They had all the guest and wedding party to the church and then the venue and then the hotel. They were so helpful as I was plannin...

g from out of town. It was perfect!

Madeline C

10/24/2022

Old Town Trolley was the perfect transportation option for our June wedding! They were much more affordable compared to other options and tons of fun. We loved having the old schoo...

l trolley as part of our day, and it was fun to drive around the city and see lots of smiles from people on the streets. The Molly trolley was perfect for escorting our wedding party (4 bridesmaids, 4 groomsmen, 4 parents, 2 grandparents, and a few other folks) from our hotel, to the ceremony in Brookline, downtown to the Boston Common for photos, and back to the reception in Cambridge. The driver was friendly and dropped us off exactly where we needed to be. He even was kind enough to turn around when we realized that we were going to get a ticket for parking our car in the wrong spot in Brookline. Kim V was super helpful in coordinating the whole day and was flexible as we were deciding where we wanted to take our photos. We highly recommend Old Town Trolley!

Molly N

6/22/2022

It was really fun to have a tour trolley be our transportation for the wedding. The driver itself took a bit of a convoluted route which took longer than expected for the first tro...

lley, but was responsive to our feedback to correct this and get back on schedule. They were responsive and rates were very reasonable. Would definitely recommend.

Julie G

11/19/2021

We hired two trolleys to transport guests from our hotels in the Boston Seaport to our venue, the Exchange Conference Center. While not a long distance, we felt transportation was ...

important to offer to our guests and Old Tow Trolleys added the perfect "Boston" and "unique" touch to our wedding! We were happy to give guests the flexibility to come and go throughout the night since we had older guests and nursing mothers. While one of the more expensive vendors for our event, it was worth it. The highlight of the night was actually getting to ride the Trolley at the end of the night, and made for the perfect photo-opt!

Katherine J

5/16/2021

I highly recommend Old Town Trolley for your wedding transportation! The Trolley was cute, punctual, clean and they were very accommodating!

Melissa P

8/18/2018

We used Old Town Trolley to get from our wedding hotel to our venue and it was perfect! Our driver was great and we were able to get some beautiful shots while on the ride over wit...

h family. Thank you so much !!

Jamie D

5/22/2018

Old Town Trolley provided transportation to and from our rehearsal dinner. They took the long way and gave a great tour to our family and friends, most of whom were from out of tow...

n. Our driver was hilarious and it was worth every penny to have such a memorable experience.

Catherine T

12/02/2015

A great way to get some extra time for yourself if you also send guests on a little tour- and a fairly inexpensive way (vs corporate buses or vans) to provide transport in a city w...

here driving is not a great option. Also, because most guests were from out of town, we also incorporated a short city tour into their ride - which, surprisingly, people loved, even on a cold November night.

Erin C

11/30/2015

These guys were great! We used them for shuttling the bridal party and wedding guests to and from hotel and museum (we did everything in one location). Leslie was fabulous, respons...

ive, and this place is much more budget friendly than going through a wedding fleet company or limo company - we compared extensively. Our driver was also on time (minus one snafu thanks to the Jets team staying at our hotel the night of our wedding - obviously not the trolley's fault). I would highly recommend these orange and green trolleys if getting married anywhere in eastern Massachusetts!

Caroline B

7/05/2015

We used Old Town Trolley for transportation from the rehearsal location and a hotel to the rehearsal dinner. The driver was prompt and navigated the downtown Boston traffic as wel...

l as possible, and the guests thought the trolley was fun. It was a beautiful day and we had the sides down for a nice breeze. Great value for what we spent. Highly recommend it!

Michelle C

9/29/2014

We used Old Town Trolley on the day of our wedding to transport the wedding party around Boston to take pictures. I worked with Leslie prior to our wedding, and we worked out a de...

tailed schedule of locations, and everything went smoothly the day of our wedding. Our wedding party had a great time listening to music as the driver took them around the city, and our driver was very professional and flexible. Overall, we had a great experience using Old Town Trolley for wedding transportation.

Amanda t

8/19/2014

Company was easy to work with and our guests were really excited to ride the trolley! More expensive than a bus, but fun for the special day!

JENNIFER B

11/18/2012

We had mostly out of town guests and transportation was important. The guests all loved the trolleys and the tours given. However, the trolley driver dedicated to the bridal party...

had no idea where he was supposed to be and when, despite my working out a very detailed contract. As a result many parts of our day were delayed which was very frustrating because we added a third trolley into the rotation to avoid this.

Service area & Contact info

380 Dorchester avenue, Boston, MA

Open map

MA
Typically included in the starting cost

(617) 269-7150

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Old Town Trolley Boston

Kimberly

Group Sales and Charters

Typically responds within 24h

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Old Town Trolley Boston

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