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Bio
Vintage Trolley Rides for all New England Events ✨ Weddings • Parties • Parades • Proms • Corporate & More 📩Inquire today to book your date!
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Recent posts
Planning your trolley experience should be just as enjoyable as the ride itself 🚋✨
Whether you’re arranging transportation for a wedding, corporate outing, private celebration, community event, group excursion, or another New England adventure, we make the Colonial Trolley booking process simple from the very beginning.
Swipe through for your step-by-step guide to getting your trolley on the calendar ➡️
📅 1. Choose Your Date
Start with the date (or dates!) you have in mind. Availability can vary throughout the year, especially during popular wedding and event seasons, so reaching out early is always a good idea.
📍 2. Reach Out
Contact our team so we can confirm availability and make sure your destination and itinerary fall within our service area. Tell us a little about what you’re planning, where you’re headed, and what you’ll need from your trolley transportation.
✨ 3. Customize Your Experience
This is where the details come together. Share your itinerary, timing, group needs, special requests, and anything else that will help us make your trolley experience fit your event.
✅ 4. Confirm Your Booking
Once the details are reviewed and everything looks right, finalize your reservation and officially get your trolley on the calendar.
Then comes the best part: the ride!
From wedding transportation and milestone celebrations to corporate events, day trips, private group transportation, and community gatherings, Colonial Trolley brings vintage-inspired charm to journeys throughout Massachusetts and New England.
Ready to start planning your event? Visit colonialtrolley.org to learn more and get in touch 💻✨🚋
19 Aug 2026
Starting the New Year with something special 🚋✨
This new logo captures the heart of Colonial Trolley; classic, nostalgic, and made for memorable moments. Endless thanks to @kylejohnston_designs for the thoughtful design. We can’t wait to see where this year takes us 🥂
01 Jan 2026
Congratulations Megan & Matt!! 🍾
@colonial_trolley
#capecodwedding #newenglandwedding #southshorewedding #capecodweddings #mawedding #dayofcoordinator #capecodweddingphotographer #capecod #rhodeislandwedding #newportweddings #wedding #riweddings #bostonbride #capecodwedding #eventplanners #weddingvenue #eventplanning #eventplannersofplymouth #eventplannersofinstagram #dayofcoordinator #dayofcoordination
31 Jul 2025
❤️We can’t wait to reveal all three decor installs in Holly. 🎄
Here is our Ralph Lauren inspired theme. Stay tuned for Gingerbread Lane 🍪and Champagne and Snow. ❄️
These are available when you book a photoshoot on @hollythechristmastrolley with @courtneyhizeyphotography
06 Nov 2026
Hello, November! A little throwback to this time last year, when families joined us aboard the trolley for some holiday fun 🎅✨
The holiday season is officially on its way, and we’re already dreaming of festive trolley rides, twinkling lights, and celebrations with family, friends, and coworkers! 🎄🚋
Whether you’re planning a company holiday outing, a family gathering, a tour of neighborhood holiday lights, or a festive celebration with your favorite people: Colonial Trolley brings a little extra holiday cheer to the occasion.
From the moment everyone climbs aboard, the journey becomes part of the celebration!
Now booking holiday events! Our holiday calendar is filling up, so don’t wait to reserve your preferred date. Contact Colonial Trolley today to start planning your holiday trolley experience!
📸 Photographer @courtneyhizeyphotography Courtney Hizey Photography
01 Nov 2026
We’re running with a skeleton crew today! 💀🚋🎃
We’ve spent some time in Salem soaking up the spooky season, and our bony passengers are ready for their next adventure. They don’t take up much room, but they do have a habit of rattling on about the ride...
Happy Halloween from Colonial Trolley! Wherever you’re celebrating, we hope your day is full of treats, good company, and a few friendly frights.
Where should our skeleton crew head next? 👻
31 Oct 2026
“We should do something special.” Here’s an idea: book a trolley. ✨
A milestone birthday. An anniversary. A reunion with people you don’t see nearly enough. Some occasions deserve a little more planning than another group text about where to meet.
Bring your favorite people together and make the ride part of the celebration with Colonial Trolley.
Have an occasion in mind? Send us your date, approximate group size, and where you’d like to go. We’ll help you explore the possibilities!
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📸 Courtney Hizey Photography, LLC
20 Oct 2026
From getting guests where they need to be on time to creating picture-perfect moments along the way, we love helping couples make transportation a memorable part of their celebration. Here is what one client had to say about their experience:
“We are so happy we hired Colonial Trolley for our wedding day. Stella is an absolute stunner and was not only a fun and memorable way to transport our guests, but also made a beautiful and unique backdrop for photos. The team was extremely helpful and punctual, which made the day run smoothly from start to finish. We truly cannot recommend them enough.”
A huge thank you to this wonderful couple for trusting Colonial Trolley with such an important day!
💍 Planning a wedding in New England? Our vintage trolleys offer a beautiful, practical, and unforgettable way to transport your wedding party and guests. We'd love to be part of your big day!
Visit our website to learn more about our fleet and inquire about availability: ColonialTrolley.org🔗
13 Oct 2026
Holly’s waking up for Christmas season. The story starts now. 🌟
11 Oct 2026
The best group outings leave room for conversation, laughter, and a few unexpected memories along the way.
Planning a celebration, team outing, or special day with your favorite people? Bring Colonial Trolley into the plans and give the journey a little extra personality. 🚋
Share your date, destination, and group size with us, and let’s talk through the possibilities.
05 Oct 2026
There’s something about climbing aboard a vintage-style trolley that immediately makes an ordinary trip feel like an experience.
Guests get to travel together, conversations continue between stops, nobody has to wonder where they’re going next, and you get a pretty great backdrop for a few photos along the way.
That’s one of our favorite things about what we do at Colonial Trolley.
Yes, we help move people from place to place ... but we also get to be part of weddings, celebrations, community traditions, company outings, family memories, and some very special days throughout New England.
Because when you’re planning an event people will remember, the experience doesn’t have to wait until everyone arrives. Sometimes it starts on the ride there.
28 Sep 2026
A little rain may have changed this weekend’s plans, but it doesn’t always have to put a damper on your event ☔️🚋
When you’re planning an event, transportation matters rain or shine.
A Colonial Trolley is more than a fun addition to your event. It’s a practical way to shuttle guests comfortably between locations while keeping everyone together, on schedule, and protected from the elements.
Hosting a wedding with your ceremony, reception, hotel, or photo locations in different places? Planning a community festival with parking or activities spread throughout town? Coordinating a corporate event, conference, holiday party, fundraiser, or private celebration?
We can help keep people moving - without asking your guests to navigate parking, coordinate carpools, or make a rainy walk from one location to another.
And on weekends like this one, there’s an extra benefit: our enclosed trolleys help keep your guests warm and dry while they travel from place to place!
Rain or shine, our trolleys are ready to roll🚋☔️
Planning an upcoming wedding, community event, corporate gathering, or special occasion? Reach out to Colonial Trolley to talk about transportation options for your event throughout New England.
25 Sep 2026
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