Boston Walking Tour of The Freedom Trail, Small Group
Overview
Available languages
1 hour 15 minutes
Mobile ticket
Join Captain Pickles, as he takes you back in time, through the American Revolution in Boston.
Take notes and ask questions on this easy stroll, as he restores lost narratives in history, about how we became American in the first place.
These tours are a movement to restore the American spirit through storytelling, connection, and shared history.
History isn’t just a series of facts and dates—it’s a living story shaped by the hands and hearts of countless individuals.
GTG's mission is to make it fun to reclaim erased narratives, reignite purpose, and empower Americans to reconnect with their shared heritage in a way that’s engaging, inclusive, and unifying.
“We are one!”
Additional Info
Wheelchair accessible
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Transportation options are wheelchair accessible
All areas and surfaces are wheelchair accessible
Not recommended for travelers with spinal injuries
Not recommended for pregnant travelers
Not recommended for travelers with poor cardiovascular health
Suitable for all physical fitness levels
What To Expect
Boston Common
The Boston Common is a public park in downtown Boston, Massachusetts. It is the oldest city park in the United States.
Massachusetts State House
Right where John Hancock once lived and now where the Massachusetts Statehouse or the New State House sits, which is the state capitol and seat of government for the Commonwealth of Massachusetts.
Options
Boston Walking Tour of The Freedom Trail, Small Group
What‘s Included
Guide will have a speaker/microphone system
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews
74 reviews
Total reviews and rating from Viator & Tripadvisor
Captain pickles, the GOAT
Sherpa05175154517,Jun 13, 2026
- Review from Tripadvisor
5.00Captain pickles (David) was without a doubt the best tour guide I’ve ever had, it’s rare to find someone who’s so in love with a city’s history and who has the charisma to share that same love with others, I was engaged, intrigued and thoroughly entertained throughout our two hour tour through the Boston commons and surrounding areas and it has been the highlight of my visit so far.
Excellent guide
GCR 11,Jun 11, 2026
- Review from Tripadvisor
5.00Excellent tour guide, very friendly and help. Made the history and information become alive would recommend thanks George and Matthew for Scotland
⭐⭐⭐⭐⭐ Must Do ⭐⭐⭐⭐⭐
reagank556,Jun 6, 2026
- Review from Tripadvisor
5.00⭐⭐⭐⭐⭐ We had a fantastic experience on the American History Freedom Trail tour. Our guide was incredibly knowledgeable, passionate, and enthusiastic about the history of Boston. They brought the stories of the Freedom Trail to life and made every stop engaging and memorable. You could tell they genuinely love sharing American history, and their energy kept the entire group interested from start to finish. I learned so much and would highly recommend this tour to anyone visiting Boston!
Great
955bradenf,May 26, 2026
- Review from Tripadvisor
5.00Really interesting learned more scone the country’s history
Fun!!!
calebf481,May 26, 2026
- Review from Tripadvisor
5.00Captain pickles is the best! A great and fun learning experience.
Best Tour Guide Ever!
rickbO6902IB,May 21, 2026
- Review from Tripadvisor
5.00Captain Pickle provided an unbelievable fact filled tour of the freedom Trail. This included me asking many times “!is that true?” or.” I don’t believe that.” it took a while to do my research as I had to deep dive into history to confirm that all the fascinating stories he told me were true. I have taken mini tours around the world and a good tour guide can make all the difference. This was without a doubt the best tour I’ve ever taken.
Loved the tour with Captain Pickles
cherylt0718,May 15, 2026
- Review from Tripadvisor
5.00We really enjoyed our tour with Captain Pickles. He was fun and also informative. He had a great spirit about him which made the tour very enjoyable. I would highly recommend this tour.
Best in Boston
thesquilly,May 8, 2026
- Review from Tripadvisor
5.00Excellent morning spent with captain pickles !! Very informative and very funny highly recommend
A great tour with a great tour guide
Explore31653042639,Apr 28, 2026
- Review from Tripadvisor
5.00It is a very nice journey with this tour guide. There are a lot of places to visit including famous places of the freedom trail. The tour guy told us about the history of the attractions and used a lot of body language that looked really funny to me. He even took his to a private library which was extremely special and others didn’t have the chance to go to.
Pickle good time
P1258LEab,Apr 10, 2026
- Review from Tripadvisor
5.00Captain Pickles did a good job. We ended up with a private tour, but it was no issue for him. He had facts on facts on facts, enough for the entire 90 minutes. I guess I'd say sometimes the stories went a little too deep into the minutia of history and over the heads of two elementary school kids, who only know the top level highlights. But he definitely had the enthusiasm. And the speaker box was much appreciated. We saw everything we wanted to see, never felt rushed, and every question of ours was met with a deep understanding of American History. Kids said afterwards that they wished he spoke more slowly.
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