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Best Walking Tours of 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.

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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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 expe-rienced tour guide doing it. As a trained ac-tor, Watson can do a variety of character accents but he naturally has an amusing Boston accent.

John Gill

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

Suzannah Dortas Prynne 

(cir. 1781) is an archetype of a colonial farmer’s wife. She hails from a small farm on the outskirts of Boston and lived through the Revolutionary Period. The tour guide is a re-tired school superintendent. She has a good voice, an engaging style, and is good with children and families.

Mrs. Silence Dogood

(cir. 1722) Widow Dogood was a humorous persona invented a young Benjamin Franklin as a hoax in the newspaper here in Boston. So many marriage proposals poured in for Mrs. Dogood that Franklin had to shut it down! As a tour guide, Mrs. Dogood is witty and intelligent, with a strong speaking voice, and a gift for communicating with people with disabilities. 

Samuel Maverick

(1753-1770) was shot and killed by British soldiers at the Boston Massacre. The tour guide has a big heart, and is especially sensitive to multi-cultural issues and remembering the historic contributions made by all Americans. He has years of experience, extensive reading in history, and a Boston accent. 

Start early at 9:30am—the earliest morning tour available of the Freedom Trail—when it’s cooler outside and less crowded! Starting early will leave you plenty of time to finish the entire Freedom Trail in one day, sightsee in historic Boston, and dine on local seafood.