Few places in our nation can claim to be the epicenter of such a staggering amount of history as Boston, Massachusetts. The city was witness to the colonial era, hosted many of the events that brought about the American Revolution, and has played a role as a significant metropolis ever since. As such, Historic Boston can be an overwhelming city to visit because the sheer number of possible activities in a weekend is overwhelming. We’ve found that it’s helpful to craft your visit around a theme, and stick to places and events within that milieu. So, without further ado, we’ve garnered a brief summary of the best historical things to see and do in Boston.

Boston Common

Boston Commons in the fall; image of foliage reflecting in the Frog Pond
Fall foliage on the Frog Pond

Founded in 1634, Boston Common is a park-like green space in the midst of the Historic Boston that has been the site of several historical events. The Commons were first used for basically any public need, such as livestock grazing, hangings, and militia training. The Colonial militia mustered there for the Revolution and then it played host to an eight-year long Redcoat encampment. In the 1860s the Commons was the stage for Civil War recruitment and anti-slavery rallies. Victory gardens sprouted in the Commons after WWI, and then for WWII all of its iron fencing was torn up and used for scrap metal. 

Today, the Commons has ballfields, America’s oldest botanical garden, and the Frog Pond, which offers ice skating in the winter and Swan Boats in the warmer months. It is still routinely used for public gatherings like political events and concerts, and it’s a local favorite for picnicking when the weather is nice. The Commons are a lovely place to walk, and we recommend starting at the Visitors’ Center, to gather brochures and embark literally on your next step: the Freedom Trail.

The Freedom Trail

circular brass plaque inset on cement, depicting the logo of the Boston Freedom Trail
Brass plaques mark the Freedom Trail

The Freedom Trail is a 3-mile walk through the city’s revolutionary history. You can choose from a number of guided tours — which are led by a 18th-century costumed character — or do one of the self-guided tours that cater to specific interests. The complete tour has 16 historic sites, including the State House, Old Granary Burying Ground (where Paul Revere, Samuel Adams, and John Hancock are buried), and the Old South Meeting House, where speeches incited the crowd to action in the Boston Tea Party. You will also see the site of the Boston Massacre, Old North Church, and then cross the bridge into Charlestown to see the Bunker Hill Monument. If you opt for the self-guided tours, you will inevitably want to stop and explore different areas that you encounter throughout the tour, so be prepared for side-journeys!

Faneuil Hall

Faneuil Hall is likely to be one of those distractions, as it’s located right next to the Old State House in Historic Boston. Known as the “Cradle of Liberty,” Faneuil Hall was built by Huguenot merchant Peter Faneuil and presented to the city on the condition that it would always be open to the public. The ground floor is occupied by market stalls selling food and gifts (often geared towards the tourist crowd). The upper floor is a council chamber — used throughout the 18th and 19th centuries and today — and the fourth floor has the Ancient and Honorable Artillery Museum

Crowds outside Faneuil Hall

The real attraction, though, is the adjoining Faneuil Hall Marketplace, which comprises three long halls (Quincy Market, North Market, and South Market) occupied by shops, restaurants, and exhibitions. When the weather is fair, street performers and buskers put on lively shows in the square. I’ve personally seen jugglers, musicians, magicians, and several circus acts there. (My family also has a long tradition of posing with the statue of a seated Red Auerbach, the legendary Celtics Coach, but you can choose whether to sit with the guy or not.)

Paul Revere House

Another site that you can see on the Freedom Trail is Paul Revere’s House. Built around 1680, it is the oldest remaining structure in downtown Boston. The site has a new education and visitor center, with displays of silver and artifacts related to Revere’s many business ventures. The coolest part of the Revere site, though, is a presentation of the story of his “midnight ride,” as told in his own words.

Old Ironsides

Photograph of three-masted ship, the USS Constitution
“Old Ironsides”

Nicknamed “Old Ironsides,” the USS Constitution is the oldest commissioned ship in the U.S. Navy, and is still commanded and crewed by Navy personnel. However, the ship is open to visitors, who are encouraged to go below decks to hear about its construction and the battles it participated in.

Across the pier, the USS Constitution Museum provides more historical context through interactive exhibits worth checking out, as well as a second ship, the Cassin Young, a World War II destroyer.

Bunker Hill Monument and Museum

New England soldiers faced the British army for the first time in a pitched battle at Bunker Hill, which is just a short walk from Old Ironsides. The Marquis de Lafayette (a recognizable name for Hamilton fans) laid the cornerstone of the monument that crests the hill: a 221-foot obelisk built from quarried granite. In the museum, you can follow a self-guided audio tour that explores the legacy of the men who fought at Bunker Hill, and discover the great lengths Bostonians went in order to construct the monument itself. 

Statue in front of a granite obelisk
Bunker Hill Monument and Statue of Col. William Prescott

Renovations have been underway for the past few years, with restoration work being done in the Bunker Hill Lodge and on the monument itself. Thankfully, in September of 2022 the $2M infrastructure improvements were officially completed, so we should be done dealing with pesky closures.

[Note: Bunker Hill and the USS Constitution are technically in Charlestown (across the river). While they may not be in Historic Boston proper, but they’re both part of the Boston National Historical Park, so we’re allowed to include it here.] 


Profile photo of Brass statue, seated figure with one foot extended.
Statue of John Harvard.

Harvard University is the oldest institution of higher learning in the United States, having been founded in 1636. It is well worth your time to stop by the Harvard Information Center to take a free walking tour of the gorgeous campus. Led by a current student, the tour is chock-full of history and Harvard lore. (For example, you’ll notice the toe of John Harvard’s shoe is a bright gold tone. It’s believed that rubbing his foot will bring you good luck, so countless students — and tourists — have rubbed it to a fine patina.)

Just off campus is Harvard Square, a hip place to hang with independent bookstores, cafés, shops, and — allegedly — more places to buy ice cream than any other U.S. city. It’s also home to several fantastic art museums: the Fogg Art Museum, which specializes in Italian early-Renaissance, and the Busch-Reisinger, with Expressionist art of central and northern Europe.

Fenway Park

Overhead shot of Fenway park, including the red seats and the boxes behind home plate
Fenway Park

Finally, no matter what your personal allegiance may be, you can’t explore Boston history without checking out Fenway Park. It has been the home of the Boston Red Sox since 1912, and is the oldest (and arguably most iconic) baseball park in the United States. Filled with quirky characteristics like the Green Monster (an extended left field home run wall, which was built taller to compensate for the park’s limited space), “The Triangle” (a dirt area to the left of the Red Sox bullpen that is notorious for granting in-the-park home runs) and a manual scoreboard, Fenway is a ballpark in a league of its own.

Even if you can’t get tickets to the game during baseball season, it is worth visiting Fenway’s “front door.” Formerly called “Yawkey Way,” the street was renamed “Jersey Street” in 2018. Good luck finding a Bostonian who actually calls it that. (It had been named after former Red Sox owner Tom Yawkey, a famed philanthropist who unfortunately ran a historically racist ball club. While the renaming was an attempt to distance the team from its racist past, Bostonians aren’t exactly known for their capacity to accept change.) The street — regardless of what you call it — is host to a veritable festival during games, with food stands and live entertainment. In the off-season it’s worth it to schedule a tour of the park, because you’ll get to experience things you never could at a game, such as standing on the infield and touring the owner’s box.

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