Where to Wine & Dine off Boston's Freedom Trail

From historic pubs to high-end restaurants, these fine establishments are not to be missed.

For any American History junkie, Boston is a fantastic travel destination—the Boston Tea Party, Battle of Bunker Hill and the Boston Massacre all happened in or near the city center, painting a very real-life picture of the American Revolution. The best way to tour these historic sites is via the Freedom Trail, a 2.5-mile long red brick route studded with 16 official site including museums, churches and burial grounds. (Editor’s pro tip: opt out of a tour and roam at your leisure, using the Freedom Trail’s website. It’s free! Just remember to charge your phone.)

All this walking and talking can be a bit taxing, leaving you parched and famished. The good news is that you don’t need to venture far from the course to find a good watering hole or restaurant—Boston, too, is rich in food and drink.

From historic pubs to high-end restaurants, these fine establishments just steps off the Freedom Trail are not to be missed:

Not far from Boston Common—the official first site on the trail—is a bar where everybody knows your name. Founded in 1969, the Bull & Finch Pub gained popularity as producers used the establishment’s exterior for the iconic show’s namesake bar. In 2002, the space was officially renamed to Cheers Beacon Hill. (It’s sister location resides near Faneuil Hall, also a stop on the Freedom Trail.) Unfortunately for fans, the downstairs bar doesn’t resemble that of the television show—a modern replica resides upstairs. And though you may not get served by Sam or partake in some brews with Norm or Cliff Claven, this is a tourist destination definitely worth popping into.

No. 9 Park
Across from the Massachusetts State House (stop two) and the Granary Burying Ground (stop three) lies esteemed chef Barbara Lynch’s flagship restaurant. Opened in 1998 in a Beacon Hill townhouse, No. 9 Park specializes in regionally-inspired Italian and French cuisine, with menu highlights including prune-stuffed gnocchi with foie gras, almond and vin santo; and Maine halibut with purple potato confit, black garlic aïoli and caviar butter. Barbara Lynch Gruppo now operates seven restaurants and has a slew of accolades. Lynch was inducted into the James Beard Foundation’s Who’s Who of Food & Beverage in 2013, and she received the James Beard award for Outstanding Restaurateur a year later.

No. 9 Park sits at the base of the Massachusetts State House. Photo by Brian Samuels.
No. 9 Park sits at the base of the Massachusetts State House. Photo by Brian Samuels.

Luke’s Lobster
Maine-native Luke Holden brought his eponymous seafood shack to New York City’s East Village in 2009, serving traceable, sustainable seafood to the masses. Since then, Luke’s Lobster has expanded to seven other U.S. states as well as Japan—get your fix at the Downtown Crossing location near the Old Corner Bookstore. If lobster rolls are your jam, you’ve come to the right place; note that these are in the style of Maine, so they’re doused in clarified butter. The beverage menu also highlights the Pine Tree State with handcrafted teas coming from Green Bee and sodas from Maine Root.

Union Oyster House
Just past Faneuil Hall—stop 11—is another tourist destination worth the visit: dating all the way back to the early 18th century, the building housing what is now Union Oyster House was first established as a silk and dry goods store in 1742. New owners took hold of the space in 1826, turning the store into an oyster bar, making the Union Oyster House one of the oldest operating restaurants in America. (It finally became a National Historic Landmark in 2003!) Traditional New England fare has and will always be served here—steamers, clams casino, chowders, Boston scrod, seafood platters, and of course oysters are all on the menu.

Green Dragon Tavern
Established in 1654, this public house around the corner from Union Oyster was used as both a tavern and meeting place for the freemasons. Historians state that the basement of the Green Dragon is the site of the headquarters of the Revolution, where notables like the Sons of Liberty would meet, and where the famous Boston Tea Party was planned. Today, the Green Dragon is a delightful respite, offering Irish-American pub fare as well as New England seafood dishes. (And should the tavern be too crowded, pop across the street to the Bell In Hand, another old-school pub that’s rich in history.)

Neptune Oyster
This modern raw bar—also located in Boston’s North End—is well worth the wait. The bulk of the oysters available come from local Massachusetts waters, with oysters from Rhode Island, Maine, the Northeastern coast of Canada, as well as Washington State, British Columbia and Alaska also on deck. Though those salty bivalves are what you came here for, the rest of the menu by chef Daniel Kang—as well as the wine list—are not to be missed.

Oysters Rockefeller at Neptune Oyster.
Oysters Rockefeller at Neptune Oyster.

Warren Tavern
Across the Charles River and down the street from the Bunker Hill Monument (stop 15) lies Warren Tavern in colonial Charlestown. Built just after the famous battle in 1775, the building was built in 1780; Warren Tavern joins the aforementioned Green Dragon and Bell In Hand as one of the oldest bars in the state of Massachusetts. A favorite of Charlestown residents—and apparently, George Washington and Paul Revere—this watering hole has an upscale bar menu featuring burrata bruschetta, a “Sons of Liberty” burger with sauteéd mushrooms, grüyére, and herb mayo, and short-rib shepherd’s pie.

Hero image by Brian Samuels.

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