8 Ways to Explore Boston Beyond The Freedom Trail

For when you're chock-full of Colonial history and want to explore other facets of Boston history and culture

Boston’s pre-Revolutionary War antics are no secret to the masses. Visitors who have been there done that along the Freedom Trail, can and should discover many other sides to this city. Here are a handful of ways to get you started.

Chinatown Market Tours

While Boston’s Chinatown neighborhood has been experiencing some gentrification in the last decade, its Asian-based community thrives, hosting festivals, food shops and dozens of restaurants serving cuisine from all over the Far East. These tours traverse the tiny, but densely populated enclave scouting out bakeries and barbecue shops, herbal pharmacies, markets, and more, as an introduction to a local heritage that some still call ‘exotic.’


Enter Boston's Chinatown through its iconic gate
Enter Boston's Chinatown through its iconic gate (©Massachusetts Office of Travel and Tourism)

Boston Photowalks

Amateur photogs enjoy this quest that educates participants on how to shoot and click with entirely different perspective, whether you spend 90 minutes in one neighborhood or a few sights in a few different parts of town. No longer is a tangible memento of Granary Burying Ground a generic snapshot of a cemetery. Instead, you learn to seek out the details, the winged effigies, a triptych of slate stones, the pennies by Revere’s Tomb.


Beacon Hill Walking Tour

Today, Beacon Hill is one of Boston’s most posh neighborhoods, and we’re talking old money. This once-monthly (first Saturday) tour, hosted by Historic New England, takes participants back to the Federal Period immediately following the American Revolution, delving into the fortunes and ambitions of the people who settled here and how those things shaped the architecture and layout that still remains.

Otis House Museum, 141 Cambridge St., Boston, MA, 617.994.5920

Context Tours

Labeled as “tours for the intellectually curious” and often led by Ph.D.-level scholars, Context Tours are intense and divided among a variety of themes. The “Boston’s Big Dig: Transforming a Cityscape” tour studies urban engineering, architecture, the shoreline and topography to tell the story of economic development and civic identity as you walk along the Rose Kennedy Greenway.


Boston By Foot

Fill 90 minutes on the weekend with a tour of “The Dark Side of Boston.” It’s one of many themes available, but we like it because it tackles topics the average sightseer might not otherwise hear about: disease outbreaks, body snatchers, robberies and the Molasses Flood. Boston by Foot is a favorite of history purists, meaning you’ll hear no tall tales on these quests.

Corner of Hanover and Cross streets, Boston, MA, 617.367.2345 

Have an adventure through the dark side of Boston's history
Have an adventure through the dark side of Boston's history (Courtesy Boston By Foot)

Black Heritage Trail

Visitors walk this route that navigates through Boston’s 19th-century African-American legacy. Fourteen stops (all in Beacon Hill) include the Lewis and Harriet Hayden House (part of the Underground Railroad) and the African Meeting House (the oldest Black church still standing in the U.S.). While it is possible to self-guide, we recommend the National Park Service ranger-led tours.

Robert Gould Shaw Memorial, 25 Beacon St., Boston, MA, 617.742.5415 

Ye Olde Tavern Tours

Perfect for Colonial history buffs who enjoy the added activity of sipping suds. Offbeat historical facts about the pre-Revolutionary era in Boston including cross-dressing soldiers and Samuel Adams’ personal hygiene make great topics of discussion while you sample locally-brewed beer at a few historic watering holes.

Corner of Park and Tremont streets, Boston, MA

The Hahvahd Tour

Founded by an alumnus and run by student guides, these walking tours traverse the grounds of Harvard University and offer insider information into the Hub’s (and the world’s) preeminent school.

1376 Massachusetts Ave., Cambridge, MA, 855.455.8747