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Boston wears its history like a badge of honor, and in this 250th anniversary year, the patriotism feels louder than ever.
This summer visitors will flock to the usual suspects: Fenway Park, the USS Constitution and Faneuil Hall. But beyond the well-known favorites, the city is filled with Revolutionary-era landmarks that even lifelong Bostonians routinely stroll past without a second glance.
Enter Michael LePage, one of the country’s most respected Paul Revere reenactors, who has spent three decades bringing the silversmith-turned-patriot to life.
LePage is often stationed at the North End’s Paul Revere House, charming visitors in full 18th-century regalia. He’s also taken part in dramatic reenactments of Revere’s midnight ride, complete with a row across the Charles River and a gallop through Charlestown. He knows Boston like the back of his powdered wig and insists that the city’s most meaningful history isn’t always where the Duck Tours stop.
Here are the historic sites LePage says locals overlook — but shouldn’t.
Dorchester Heights, Dorchester
“Ask the average Bostonian if they’ve been to Dorchester Heights and most would probably say ‘no,’ ” said LePage. That’s surprising, given that this unassuming hill overlooking the harbor is where George Washington positioned his cannons in March 1776, forcing British Gen. William Howe and his troops to retreat and never return. Today, it’s a quiet park with a monument and sweeping views. “For such a pivotal site, it’s remarkably under visited,” said LePage.
Paul Revere’s Waterfront Landing, Charlestown
You’ll really have to hunt for this one: It’s tucked behind an active construction site adjacent to an office building, but search the waterfront just a few yards south of the USS Constitution and you’ll find a plaque commemorating the landing site where Paul Revere arrived from across the river on the fateful night of April 18, 1775. “People walk the Freedom Trail over to Charlestown to see the Constitution or Bunker Hill, but they miss the fact that this was where Paul Revere landed to begin his midnight ride,” said LePage.
Castle Island, South Boston
You’ll have to go well across all of Southie to get to this pre-Revolutionary monument, but make the trek and you’re rewarded with one of the most scenic parts of Boston. Originally built in the early 17th century as Castle William, this British stronghold was used as a fortification to protect the colony from pirates and as a prison for captured Native Americans who were sold into the Atlantic slave trade. It changed hands in 1776, was renamed Fort Independence, and today is one of the best spots in the city for a walk or bike ride. Be sure to get a lobster roll from Sully’s, which won the James Beard Foundation’s America’s Classics Award in 2025.
Burying Grounds
Boston’s colonial past isn’t limited to its buildings and established tours. A self-guided walk through the Old Granary, Copp’s Hill , and King’s Chapel Burying Grounds reveals deeply personal stories. “It’s not just about the famous names,” explained LePage. “It’s the inscriptions, the symbols, and the way families were memorialized.” Of particular note is the Phipps Street Burying Ground in Charlestown, the final resting place of John Harvard, now tucked behind a Whole Foods.
Blackstone Block
Visitors and locals alike know the Union Oyster House and Bell in Hand Tavern as two of the most historic — yet still excellent — pubs in town, but LePage encourages everyone to take a step back and consider the cobblestone streets and the low-slung buildings that predate the Revolution. “That whole area is called the Blackstone Block. When you walk down those narrow streets, you really get a feel for what colonial Boston looked like.”
Royall House and Slave Quarters, Medford
Ask any local and they’re unlikely to have even heard of this historic home located just outside the city limits. It once belonged to one of the most powerful slaveholding families in Massachusetts. “It’s not just about the Royall family, but about the enslaved people who lived there,” said LePage. “It’s important that we tell the whole story — not just talk about the wealthy owners.”
Shirley-Eustis House, Roxbury
In the heart of a residential neighborhood better known for its African American culture and three-decker houses stands a testament to another time: the Shirley-Eustis House, a wealthy colonist’s former summer estate. This well-preserved Georgian mansion serves as a reminder that Revolutionary Boston wasn’t confined to a single neighborhood, but stretched across communities that still define the city today.
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