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Image by Leonel Heisenberg

The Freedom Trail


The Freedom Trail is a red brick line on the sidewalk to follow on foot. The red line connects 16 historic sites along a gentle 2.5-mile walking trail, starting at Boston Common and ending at the Bunker Hill Monument in Charlestown. The narrated walking tours of the Freedom Trail are led by experienced tour guides and cover the first 11 historic sites of the Freedom Trail. Beginning at Boston Common and ending at Faneuil Hall, the 90-minute walking tour adds richness to the experience of the Freedom Trail. Boston’s Revolutionary history is explained by “historic figures” dressed as they did in the colonial period.

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Our Guides


James Otis

James Otis

(1725-1783) is famous for the rallying cry “Taxation without representation is Tyranny!” The tour guide, Donald Watson, was the first to portray an historic character in costume on the Freedom Trail, and is the most experienced Freedom Trail tour guide. As a trained actor, Donald can do a variety of character impersonations, but as a Boston native, he naturally has an amusing Boston accent.

John Gill

John Gill

(1732-1785) was a partner at printers, Edes & Gill, of the patriotic colonial newspaper, The Boston Journal. As a tour guide, John is funny and knowledgeable about the area, with an instinct for addressing areas of confusion. He is a Bostonian with a native Boston accent.

Nabbie Cranch Smith.jpg

Nabbie Cranch Smith

is envisioned as a delightful, fictitious confidant of John & Abigail Adams. The tour guide is a retired 5th grade teacher, traditionally, the year Massachusetts school children study the Revolutionary War. She has a strong voice and is good at engaging teenagers and young people.

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