Go on a Historic Walking Tour 

Their boots were made for walking; in fact, the typical American Revolution army footed it an average of 10 to 15 miles a day. So, buckle up for these walking tours in towns that played pivotal roles in the Revolutionary War. You’ll walk the talk of things learned in textbooks for some enlightenment and exercise—a win-win. And you’ll saunter away with a sense of pride and enthusiasm for the USA’s 250th, which really springs to life in this neck of the woods.

Salem

It’s no mystery that Salem is home to all things witchy. After all, the Salem witch trials transpired here. Less transparent is the 400-year-old town’s role in the Revolution. Yet Salem was home to patriots, privateers, and events that helped win the fight for the nation’s independence. Witch City Walking Tours wisps through Salem, celebrating the town’s spirits—both ghastly and patriotic.

Gloucester

The Revolution brought us freedom, and the self-guided Gloucester HarborWalk is free to explore. The 1.2-mile walkway—with 42 strategically planted granite posts—navigates the nation’s oldest seaport town. You won’t need a lantern like our forebears but will need a smartphone to “hear ye, hear ye!” insightful info. Revolutionary sites include Stage Fort Park, which will host a reenactment of the Battle of Gloucester June 21 to 22, 2026.

Ipswich

Take a  Historic Ipswich walking tour led by local historian Gordon Harris to parade through the town’s remarkable sites. Stops include Treadwell’s Tavern where John Adams was a frequent guest and which hosted the 1774 Essex County Convention that voted to establish a Provincial Congress. Harris also conducts custom genealogy tours for those with ancestral Revolutionary ties.

Essex

“One if by land, two if by sea” resonates at the annual two-week-long Trails & Sails event held by the Essex National Heritage Area each September. One fascinating surf-and-turf-oriented walking tour explores the evolution of coastal farming at  Cogswell’s Grant, from its inhabitation by Indigenous people through the Revolutionary period to the present day. Mark September 12 to 27 for 2026’s happenings.

Newburyport

Explore the lanky necklace of 13 self-guided Clipper Heritage Trail walking tours in this storied maritime town. Celebrated sites include St. Paul’s Episcopal Church, one of two Anglican churches in Massachusetts that remained open during the Revolutionary War, where the Declaration of Independence was read in 1776 by Tristram Dalton, who became Massachusetts’ first U.S. senator.

This blog is an excerpt from our digital guide “250 Ways to Explore, Discover, and Celebrate North of Boston”. To view the full guide, click here.