Boston for History Buffs

In a venerable city such as Boston, how can one possibly curate a list of the top 20 things a history buff should see? The simple answer is: One can't. 

So Much History, So Little Time

However, that doesn't mean we won't try, giving a few provisions, of course:

We omit individual Freedom Trail sites (there are 16 of them), lumping them all into the single nomination "Freedom Trail." The disappointed reader can browse our guide for how to best do this walk through Colonial and Revolutionary history in one day, here in our guide to exploring Boston's Freedom Trail.

We've included at least one item from each of America's five centuries, 17th through 21st.

We've performed a broad sampling of all of Boston's historical interests, whether they be political, military, intellectual, cultural, or just plain rebellious. 

Yes, we've left some historic sites and attractions out and likely neglected to mention favorites. But, all the more reason to explore our site and then head out to explore Boston.

Charlestown Navy Yard

Located where the Charles River meets Boston Harbor, this 30-acre Boston National Historical Park served the Navy for 174 years and was integral in military engagements from the War of 1812 to WWII.

John F. Kennedy Presidential Library and Museum

Dedicated to JFK, spotlighting such subjects as his childhood, the 1960 campaign, the Cuban Missile Crisis, the Space Program and civil rights. The Museum utilizes remastered historic film footage and a number of interactive displays. Open daily 9 am-5 pm. Admission: $10-14, free ages 12 and under.

The Freedom Trail

Focused on the American Revolution, from the Colonial period to the War of 1812, this 2.5-mile, red-painted and bricked path connects 16 historic sites, each of which has its own story. Visitors can walk the trail at any hour, but accessibility to each site varies, with most open daily 9 am-4/4:30 pm.

North End

Red sauce bubbles in kitchens throughout this long-lived sector that is awash in Italian heritage; although, it has not always been this way. It was Boston’s original posh neighborhood, and Thomas Hutchinson and Paul Revere lived here.

Boston Public Library

America’s first municipally-funded public library houses millions of books, manuscripts, music scores and art and boasts a scenic courtyard, events, readings and exhibits. Free art and architecture tours available.

Boston by Foot

These guided, 90-minute tours are indeed conducted on foot. Regularly offered tours include Back Bay, Beacon Hill, Heart of the Freedom Trail, the Dark Side of Boston and a literature-focused tour. Tours depart multiple times daily, and schedule varies. Tickets: $10-20.

Captain Jackson's Historic Chocolate Shop

History buffs with a sweet tooth can stop into this interactive living history exhibition located on the Old North Church campus. The store interprets the history of chocolate, focusing on how it was made and consumed in Colonial America.

Harvard Yard

The familiar idiomatic statement that you can “pahk yah cah” here isn’t exactly accurate. Harvard Yard is encircled by a wrought iron and brick wall that serves as a road block for most motor vehicles.

Liberty Fleet of Tall Ships Boston Harbor Sails

Two majestic schooners offer passengers adventure, New England romance, and a fun time for families—you even get to hoist the sails. Departs June 3-Sept. 24, daily at 10:30 am, noon, 12:30 pm, 2:30 pm, 3 pm, 4:30 pm, 6 pm and 6:30 pm.

Fort Independence

Five-bastion Fort Independence has been the site of Boston’s sea defense since 1634, although the existing structure dates to 1851. The pentagonal fort was primarily used for training local soldiers and confining prisoners of war as early as the American Revolution.

Black Heritage Trail

This walking route explores the history of the African American community in 19th century Boston with 14 different stops including the bronze Robert Gould Shaw Memorial, the Lewis and Harriet Hayden House (a stop on the Underground Railroad), and the African Meeting House, which is the oldest Black church still standing in th

Boston Tea Party Ships Museum

This center provides a unique, immersive experience set during a historic time period (1773-1775). Live actors, tea-tossing reenactments, high-tech interactive exhibits, a film and three authentically restored tea ships tell the full story of the Boston Tea Party and its immediate aftermath.

Ether Dome at Mass General Hospital

More than 8,000 operations took place here from 1821-1868, but the Ether Dome is particularly significant because it is the site where Dr. John Warren performed the first surgery without the patient experiencing pain.

Ye Olde Tavern Tours

This walking tour is perfect for history buffs who enjoy sipping suds, too. Spend an afternoon learning offbeat facts about the pre-Revolutionary era from your PhD-educated guide.

Chart House

Located on historic Long Wharf, this local landmark was built around 1763 and once held the offices of patriot John Hancock. Today, many fixtures remain, such as the broad wooden beams, floors, brick walls, staircase, and even Hancock’s safe.

New England Historic Genealogical Society

The oldest and one of the largest genealogical societies in the U.S. has been dedicated to “collecting, preserving and interpreting” annals of family and local history and genealogical records since its founding in 1845.

Boston Logan International Airport 9/11 Memorial

This 2.5-acre site is a memorial to Sept. 11, 2001. A large, square glass sculpture contains etched panels with the names of passengers on American Airlines Flight 11 and United Airlines Flight 175, the two flights that originated at Logan International Airport.

Warren Tavern

Once a swill spot for Paul Revere, this historic watering hole has been serving pints since 1780, and it boasts an interior reminiscent of an old English pub and decor that is decidedly 18th century. The tavern is still a beloved Charlestown gathering place to which spirited crowds gather for (free) live music W-Th.