
Boston Walking Tour of The Freedom Trail, Small Group
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.9/5
Based on 82 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Boston Walking Tour of The Freedom Trail, Small Group worth booking?
Boston Walking Tour of The Freedom Trail, Small Group is a 1.3-hour experience in Boston, United States, from $25 per person. It scores 77 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.9/5 rating across 82 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 77 / 100
- Rating
- 4.9/5 (82)
- Duration
- 1.3 hours
- From
- $25 per person
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 i
What you get
About this experience
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!”
What's included
Included
- Guide will have a speaker/microphone system
What you'll see and do
Boston Common
The Boston Common is a public park in downtown Boston, Massachusetts. It is the oldest city park in the United States.
10 minutes here
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.
5 minutes here
Park Street Church
Park Street Congregational Church, founded in 1809, is a historic and active evangelical congregational church in Downtown Boston.
5 minutes here
Granary Burying Ground
We'll stop by the final resting places of James Otis, Paul Revere, Samuel Adams and others.
15 minutes here
King's Chapel
Established in 1630, it is the oldest graveyard in the city and is a site on the Freedom Trail.
Pass by without stopping
Statue of Benjamin Franklin
Site of the Boston Latin school, currently where the Old City Hall is at.
7 minutes here
Old South Meeting House
built in 1729. It gained fame as the organizing point for the Boston Tea Party on December 16, 1773.
7 minutes here
Old Corner Bookstore
It was built in 1718 as a residence and apothecary shop, and first became a bookstore in 1828.
Pass by without stopping
Boston Massacre Site
Located outside of the Old State House is the Boston Massacre Site.
5 minutes here
Old State House
The Old State House, also known as the Old Provincial State House, is a historic building in Boston, Massachusetts, built in 1713.
5 minutes here
Faneuil Hall Marketplace
Great place to end the tour, by the statue of Samuel Adams. This location has bathrooms, local food and a free museum.
10 minutes here
Where it starts and ends
Meeting point
Boston
Put "Boston Common Visitor Center" in your maps, it's right off the Boston Common and Park Street Station. You will find your costumed guide at this location. Make time for parking.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
The Tour Ends at the Samuel Adams statue. Faneuil Hall Marketplace, where you can easily find souvenirs, local food and bathrooms.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Guided Tours Guild
Know before you go
- 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
Photos






What travelers are saying
Outty’s summary of the themes that recur across 82 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
8 mentionsReviewers describe the commentary as informative rather than scripted.
The guide
5 mentionsTravelers single out the guide as the reason the experience works.
Traveler reviews
82 verified traveler reviews for Boston Walking Tour of The Freedom Trail, Small Group. Ratings and reviews provided by Viator and Tripadvisor.
Highly recommend Freedom Trail Tour
I had such a great experience on the Freedom Trail tour with David! I learned so much, and I really appreciated how he went beyond the history we typically learn in school. He did an excellent job sharing the stories and perspectives of people whose contributions have often been underrepresented, including Native Americans, women, and people of color during the American Revolution. David is an amazing storyteller who makes history interesting, engaging, and easy to connect with. You can tell he is incredibly knowledgeable and passionate about what he does. I walked away with a much deeper understanding of Boston’s history and the American Revolution. I definitely recommend taking a tour with David. You’ll learn a lot and have a great time doing it!
via Tripadvisor
Great for kids
Kids really enjoyed Captain Pickles. We walked around Boston and learned about different people and places.
via Viator
Highlight of my trip!
Great leader, shared so many inside stories and such cool information. Highlight of my trip!
via Tripadvisor
Amazing Insighful Thougt provoking
He was the consummate professional. His breadth of knowledge was not amazing but insightful. He explained so much that we didn't know including the impact of the native Americans and indigenous peoples on the United States He is the best tour guide in Boston Many stopped to take pictures with him in his period attire.
via Viator
Very passionate
Very passionate. And knowledgeable Many interesting sites and history Perfect amount of time to see plenty of Boston
via Viator
Good to know
- Duration
- 1.3 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 29
- Verdict
- Strongly Recommended
Why this scores 77
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Boston Walking Tour of The Freedom Trail, Small Group: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Boston.
How much does Boston Walking Tour of The Freedom Trail, Small Group cost?
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Prices start at $25 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Boston usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Boston Walking Tour of The Freedom Trail, Small Group take?
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Plan for about 1.3 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Boston is not rushed.
Is Boston Walking Tour of The Freedom Trail, Small Group worth it?
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It holds an Outty Ranking of 77 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.9/5 across 82 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Boston, and how flexible the cancellation terms are.
Can I cancel or reschedule Boston Walking Tour of The Freedom Trail, Small Group?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Boston Walking Tour of The Freedom Trail, Small Group suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 1.3-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Boston Walking Tour of The Freedom Trail, Small Group?
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Around 29 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Boston can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Boston and add a light layer if any part of the 1.3-hour experience runs outdoors or after sunset.
Where does Boston Walking Tour of The Freedom Trail, Small Group start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Boston within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Boston?
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Boston is compact enough that a good walking guide beats any bus. Freedom Trail walks, harbour cruises, Fenway tours and whale-watch runs out to Stellwagen Bank are the core, plus Salem and Cape Cod as day trips. Outty Ranking weights guide storytelling and group size heavily, because on the Freedom Trail the narration is the entire product. On Outty we rank every Boston experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Full Revolutionary Story Epic Small-Group Boston Walking Tour, Boston: Freedom Trail History Small Group Walking Tour, Boston's Freedom Trail: A Revolutionary Walking Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Boston?
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May to October. Whale watching runs roughly April through October only. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Boston?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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