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About

Lessons on Liberty™ provides affordable 90-minute walking tours of Boston’s Freedom Trail.  Our intimately-sized tours operate seven days a week from late March to October 31.  All of our tour guides are degreed historians who bring a vast knowledge and understanding of revolutionary Boston. We concentrate on the critical events that lead to the American Revolutionary War and guarantee Lessons on Liberty to be the most authentic and accurate walking tour in Boston.

Lessons on Liberty was founded by people engaged in the “living history” hobby of portraying the Revolutionary War period, 1765-1783. Dressed in historically correct 18th century clothes, our living historians/reenactors accurately portray life in provincial Boston. We were founded with a genuine dedication to bring you accurate educational tours based on factual historical research.

Our founder, Gary Gregory, has reenacted the battle of Lexington and Concord, the Battle of Monmouth,  Battle of Road Island, Strawberry Banke, and Saratoga as  a reenactor. He has also volunteered at Minuteman National Park. Gary has produced the annual Boston Tea Party for the Old South Meeting House in Boston and is a member of the Committee for the Boston Massacre Reenactment. He is a member of the Tenth Massachusetts Continental Regiment who are known for historical exactness in their reenactment of this Revolutionary War regiment. Most recently, Gary opened The Printing Office of Edes & Gill, the only colonial printing experience located along the Freedom Trail.

Lessons on on Liberty is a 501(c)3 non-profit corporation.

Freedom Trail is a registered trademark of the Freedom Trail Foundation.

*Lessons on Liberty, as featured by AAA on its Boston Greatest Hits Map (shown above).