Blaze Your Trail in Massachusetts

Sponsored by the Massachusetts Office of Travel and Tourism

The Revolutionary War comes alive not through its facts and dates, but through its stories. Who can resist the thrill of Longfellow’s “Listen, my children, and you shall hear / of the midnight ride of Paul Revere”? Seeking to relive such world-famous tales from our nation’s founding, millions of people walk Boston’s Freedom Trail each year, past the Bunker Hill Monument, Old North Church, and other sacred spots. 

Yet Massachusetts — the birthplace of the American Revolution — has many more stories to tell, in cities and towns all across the Commonwealth. Rich with history that’s often lesser known, they invite you to march to the beat of a different drummer, and set off on a rebel’s road trip.

1. Boston

The legendary home of the Boston Tea Party also saw George Washington’s first campaign as commander in chief of the Continental Army. During the 1775–1776 Siege of Boston, Roxbury’s Dillaway-Thomas House served as army headquarters overlooking Dorchester Heights, where the Americans’ cannons ultimately spurred the British to flee.

Another patriotic stop off the beaten path is the Boston Women’s Memorial, which honors such luminaries as Abigail Adams, one of the nation’s Founding Mothers, and Phillis Wheatley, a trailblazing 18th-century Black poet whose work explored ideas of freedom, slavery, and the Revolution.

2. Melrose

On May 27, 1776, Malden (including what is now Melrose) became the first town in the colonies to cast an official vote to secede from England. Toast that milestone at Melrose’s Rising Eagle Publick House, an homage to the bygone tavern where Revolutionary firebrands once gathered.

3. Lexington

Tucked in among the more famous sites connected to the Battles of Lexington and Concord is a quiet tribute to a singular patriot: The Prince Estabrook Memorial, near Buckman Tavern, honors this enslaved man who joined the minutemen on April 19, 1775, becoming the first Black soldier to fight in the American Revolution.

4. Weston

As Massachusetts’s 250th anniversaries go, here’s a sneaky surprise: The exhibit “Spies Among Us” at the Golden Ball Tavern Museum marks a February 1775 visit to the tavern by British undercover agents, and delves into the use of espionage on both sides during the war. This museum is one of the rare institutions to tell the Loyalist story — and does a fascinating job of it.

5. Worcester

The first thing ever printed in the city of Worcester was the May 3, 1775, edition of The Massachusetts Spy, carrying an eyewitness account of the Battles of Lexington and Concord. Isaiah Thomas had relocated his influential newspaper from Boston just weeks earlier, smuggling out his printing press in the dark of night. Nicknamed “Old No. 1,” that same press can be seen today at the American Antiquarian Society, founded by Thomas himself.

You can also take a historic walking tour to discover the city’s other claims to fame, including the event that some say was the true start of the Revolution: the 1774 Worcester Revolt, which effectively ended British authority in Central Massachusetts.

6. Springfield

On his daring mission to deliver 60 tons of artillery from Fort Ticonderoga to Boston in 1775–1776, Colonel Henry Knox made several stops along his 300-mile route to rest and resupply. Among them was Springfield, which looked to Knox like a prime spot for storing weaponry far away from British eyes. At Knox’s suggestion, General Washington established the first federal arsenal here in 1777; less than 20 years later, it became the nation’s first armory and would serve as the center for manufacturing U.S. military small arms well into the 20th century. Now preserved as the Springfield Armory National Historic Site, it offers a unique look at the hard work of defending liberty. 

7. Stockbridge

Through 11 sites dotting Main Street, the Mohican History Walking Tour tells the story of the Indigenous people who not only lived in this community alongside colonists in the 1700s, but also fought for the Patriot cause. The nearly 60 Stockbridge Mohicans who volunteered were among the first Native Americans on either side to take part in the war. Washington showed his thanks by sponsoring an ox-roast feast here in 1783, even as the Mohican people were then being forced to move west.

8. Deerfield

Squint just a bit and you’re back in the 1700s at Historic Deerfield. At one of the only authentic Colonial villages in the United States, there’s something to discover around every corner, from an elegant porcelain tea set used by a Loyalist family to a powder horn belonging to Massachusetts native Israel Putnam, whom many believe was the commander who shouted the unforgettable order at Bunker Hill: “Don’t fire until you see the whites of their eyes!”

For more revolutionary travel inspiration and itineraries, visit: massachusetts250.org

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