The 10 Best Dishes to Eat Along the Freedom Trail

From Boston cream pie in a Downtown hotel to brick-oven pizza in Charlestown
March 18, 2015
by Scott Kearnan

Behold! The snow is melting and we can finally see sidewalks again. Getting out into the fresh, slightly warmer air never felt so good, and with the first day of Spring coming up on Friday, we turned our attention to Boston's most famous walking route: the Freedom Trail, that 2.5-mile-long path of red brick that passes through some of the city's (and really, the country's) most historic landmarks. Lace up your sneakers and prepare for a spring stroll; if you need to stop to eat along the way, here are a handful of meals that have become legendary in their own right. 

Prix fixe dinner at No.9 Park

Dine in the shadow of the gold-domed State House, watching the well-heeled modern blue bloods of Beacon Hill traipse by Boston Common. Maybe you can't afford to eat like this every night, but a three-course dinner ($69) at star restaurateur Barbara Lynch's long-standing icon is something that every Hub-dweller must experience at least once. And since it's positioned by the Downtown "start" of the Freedom Trail, you'll have over two miles ahead to walk off that dinner. 

9 Park St.; 617-742-9991

Boston cream pie at Parker's Restaurant

Parker's is tucked inside the Omni Parker House Hotel, a property with amazing history in itself. America's oldest continuously operating hotel, it has the stories to show it: here Malcolm X worked as a busboy and Charles Dickens wrote A Christmas Carol. Parker's, with its Brahmin-apropos dark woods and gilded accents, is also where John F. Kennedy proposed to Jacqueline Bouvier (at Table 40), and you can celebrate your own romantic stroll here by splitting a Boston cream pie, Massachusetts's state dessert, which was invented at the hotel.

60 School St.; 617-227-8600

Burger at B.Good

Want to grab a quick burger as you snake your way through Downtown? Skip the standard fast-food spots and opt for this small Boston-born chain offering comparatively healthy takes on the all-American classic. Expect farm-to-table beef, local in-season ingredients and other "real-food" approaches to the quick-service concept. There are standout seasonal veggie burgers (like the "West Side" of avocado, cilantro, fresh salsa and chipotle purée), and instead of the calorie-loaded shakes typical of fast-food eateries, you'll even healthful options like a kale crush smoothie featuring local apple, pear, banana and apple cider.

255 Washington St.; 617-227-1006

Country rabbit sausage at The Tap Trailhouse 

Boston Nightlife Ventures did a fine job late last year renovating the sticky-floored, Faneuil Hall-side dive bar The Tap into something similarly accessible but a lot more sleek — and armed with an elevated culinary program devised by Bill Brodsky, the group's new culinary officer. Taking inspiration from the Freedom Trail out front, the restaurant wanted to put modernized twists on classic Yankee fare. The results include our favorite app: a tender, slightly spicy sausage made from rabbit butchered in-house, set atop the sweet cornmeal flatbread of a maple sugar johnnycake. A handful of pickled cranberries offer just enough pleasant tartness. Wash it down with a pint of Trailhouse Ale, brewed exclusively for restaurant by Rhode Island micro Newport Storm. Look for the tap handles that are replicas of Colonial-era guns. 

19 Union St.; 617-367-0033

Poutine at Saus

In modern times, Faneuil Hall is known as much for its scene of drunk bar crawlers tottering across cobblestones as for its Colonial history. You don't need to be sauced (though it helps) to enjoy the preemptive hangover cure that is Saus's signature poutine: frites topped with cheese curds and gravy. Ask for it with "the works" to add beer-braised beef, bacon bits, truffled mushrooms, pork belly and a deep fried egg. We're drunk in love. 

33 Union St.; 617-248-8835

Clam chowder at Union Oyster House

Is it a tourist trap? Yes, and for a good reason. Opened in 1826, Union Oyster House is recognized as America's oldest restaurant. And cooler-than-thou contrariness be damned, the famed clam chowder deserves its plaudits. Plus you can slurp away in Booth 18,  the "Kennedy Booth," where devotee JFK most frequently enjoyed his chowder. 

41 Union St.; 617-227-2750

Bolognese at Bricco

The North End is filled with red-sauce Italian joints, some a lot better than others. How to choose one spot? We are talking about history, after all, so we have to tip our hat to this stalwart from restaurateur Frank De Pasquale, a founding father of the neighborhood's restaurant scene. (His other ventures include Mare, Trattoria Il Panino and Quattro, among others.) Fill up on some of the spot's signature Bolognese, then hit its neighboring market, Bricco Salumeria, to stock up on Italian groceries from deli meats to imported cheeses.

241 Hanover St.; 617-248-6800

Fettucini Strega at Strega Ristorante

Speaking of local restaurateurs, you have to hand it to Nick Varano, the onetime car salesman who realized his American dream by opening Strega in 2003. Its signature fettucini has been on the menu ever since: homemade pasta tossed with jumbo shrimp, pan-seared scallops, baby spinach and a creamy house sauce. Since then, the Varano Group of restaurants has grown to include the Seaport's Strega Waterfront, Woburn's Strega Prime and Park Square's (soon-to-open) Strip by Strega, among others. But nothing beats a true North End original. 

379 Hanover St.; 617-523-8481

Tacos at Papagayo

Feeling famished after you cross the bridge to Charlestown? Fear not. Right on the other side awaits an outpost from this small local chain of casual Mexican restaurants, where you'll find a splay of street tacos served three to an order, including the fish tacos of pan-seared tilapia, with avocado, garlic mojo and cabbage slaw; and "trailer park tacos" filled with crispy chicken, chile con queso, shredded lettuce and pico de gallo.

1 Chelsea St., Charlestown; 617-242-7400

Pizza at Legal Oysteria

As you reach the end of the Freedom Trail, reward your walking with a hearty dish at the latest one-off concept from a long line of Boston seafooders. Opened last summer, the Italian-inflected Legal Oysteria has plenty of fab fish — but it also makes use of the brick oven left behind by the landmark spot's former inhabitant, Todd English's first restaurant Olives. And yes, Legal can spin a strong pie, like the sopressata topped with stracciatella, banana peppers and a spicy red sauce.

10 City Square, Charlestown; 617-712-1988

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