Tours/Boston/Boston Walking Tour of The Freedom Trail, Small Group
Viator · group up to 40 pax

Boston Walking Tour of The Freedom Trail, Small Group

4.9(81)Boston1 hour
VIATOR4.7(36)TRIPADVISOR5.0(45)

Description

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!”

Tour Options

Boston Walking Tour of The Freedom Trail, Small Group

Itinerary

10 min

The Boston Common is a public park in downtown Boston, Massachusetts. It is the oldest city park in the United States.

5 min

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 min

Park Street Congregational Church, founded in 1809, is a historic and active evangelical congregational church in Downtown Boston.

15 min

We'll stop by the final resting places of James Otis, Paul Revere, Samuel Adams and others.

Pass by

Established in 1630, it is the oldest graveyard in the city and is a site on the Freedom Trail.

7 min

Site of the Boston Latin school, currently where the Old City Hall is at.

7 min

built in 1729. It gained fame as the organizing point for the Boston Tea Party on December 16, 1773.

Pass by

It was built in 1718 as a residence and apothecary shop, and first became a bookstore in 1828.

5 min

Located outside of the Old State House is the Boston Massacre Site.

5 min

The Old State House, also known as the Old Provincial State House, is a historic building in Boston, Massachusetts, built in 1713.

10 min

Great place to end the tour, by the statue of Samuel Adams. This location has bathrooms, local food and a free museum.

Highlights

Guide will have a speaker/microphone system

What's included

Included
Guide will have a speaker/microphone system

Traveller Ratings

4.9
81 reviews
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Important Information

  • 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

Reviews(81)

A
Amanda_H
July 21, 2026
Great for kids

Kids really enjoyed Captain Pickles. We walked around Boston and learned about different people and places.

I
I2332RLbellal
July 18, 2026
Highlight of my trip!

Great leader, shared so many inside stories and such cool information. Highlight of my trip!

H
Heather_D
July 6, 2026
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.

T
Tammy_s
July 5, 2026
Very passionate

Very passionate. And knowledgeable Many interesting sites and history Perfect amount of time to see plenty of Boston

A
Anastasia_H
July 2, 2026
No show for our tour today.

We were so excited for this tour and got to our location ready to go- only to find out the tour was cancelled and nobody notified us. Very very disappointing to come all this way and not be given any information about the cancellation. The visitor center said the guide told them he wasn’t coming in for the tour. Trying to get a refund from viator and find something else to do here in Boston today.

D
Denyse_K
June 17, 2026
Small Group Freedom Trail

The tour with “Capt Pickles” was so worth it! Educational, entertaining and inspiring… this is a must do when in Boston!

E
E5606LClindseys
June 17, 2026
Great

Our guide (Captain Pickles) was extremely knowledgeable and entertaining. We learned a lot about history that isn’t something you learn from school history books. We highly recommend this tour to anyone visiting the Boston area.

S
Sherpa05175154517
June 13, 2026
Captain pickles, the GOAT

Captain 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.

G
GCR_11
June 11, 2026
Excellent guide

Excellent tour guide, very friendly and help. Made the history and information become alive would recommend thanks George and Matthew for Scotland

R
reagank556
June 6, 2026
⭐⭐⭐⭐⭐ Must Do ⭐⭐⭐⭐⭐

⭐⭐⭐⭐⭐ 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!

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