When people think of the Boston neighborhood of Charlestown, often the first thing that comes to mind is the Ben Affleck movie “The Town.” While Charlestown does have a bit of a gritty, working class history, it is also one of Boston’s most charming neighborhoods with its brick sidewalks and gaslamp-lined streets. When traveling to Boston, Charlestown is a great neighborhood to visit. Having lived in Charlestown for the past three years myself, see my recommendations for the best things to do in the neighborhood below.
Charlestown’s Best Historic Attractions
While less touristy than other parts of town, Charlestown is a very historic neighborhood and is home to a few of the historic sites on the Freedom Trail. Many visitors to Boston will cross the bridge over to Charlestown from the North End to see the USS Constitution (the oldest commissioned ship in the United States Navy). Located in the Navy Yard, it’s a fun area to walk around and explore. After visiting “Old Ironsides” (the nickname given to the ship) it’s fun to continue up to the Bunker Hill Monument, where you can climb the 294 steps for great views of Boston. Even better, bring a picnic and people-watch at the site of the first major battle of the American Revolutionary War: The Battle of Bunker Hill.
Just a few blocks down from the Monument, Charlestown is home to one of the most historic taverns in the country (also the oldest tavern in Massachusetts): The Warren Tavern. Beloved by locals and visitors alike, The Warren Tavern once served guests including George Washington and Paul Revere. Built in 1780, it remains a great neighborhood spot to get a pint and a snack. I especially enjoy their thick, creamy clam chowder, fish & chips and short rib shepherd’s pie. They also offer one of the best lobster rolls in the neighborhood (pictured below).
Best Restaurants in Charlestown
After walking around and taking in Charlestown’s history, you may just work up an appetite. Recommendations for where to grab a bite in the neighborhood follow below.
Navy Yard Bistro
1 6th Street, Charlestown
Located just around the corner from the USS Constitution, The Navy Yard Bistro is a great place to stop for dinner. Open for dinner Tuesday-Sundays, The Navy Yard Bistro offers outdoor seating on its patio during the warmer months, and also has a cozy indoor bar and dining room. Serving comfort food with an innovative twist, the restaurant offers a nice wine list, along with a selection of local craft beer. For starters, I recommend the Red & Golden Beet Salad (the truffled vinaigrette is amazing!) and the confit Duck Wings. For entrees, I love the Pan-Seared Cod with coconut curry, the short rib, and the Bistro Chicken (which my husband gets every single time we go).
Figs by Todd English
67 Main Street, Charlestown
Our favorite pizza spot in Charlestown, Figs is a true neighborhood gem. Tucked away on Main Street, Figs offers a creative menu of artisan pizzas, plus salads and pasta. Their tagline is “never trust a round pizza,” and you’ll notice all pizzas are freeform in shape with a very thin, crispy crust. We almost always start with the Chicken Parmesan Sliders or the Greek Salad. The pizzas are large, so if you want to try two different kinds, I recommend going half and half. Our typical order is half a Bronx Bomber (pepperoni with fresh basil) and half a Red Sox (caramelized onions, peppers, sweet sausage and aioli). Other popular options include the Fig & Prosciutto and the Crispy Eggplant.
Best Places For Cocktails in Charlestown
Pier 6
1 8th Street, Charlestown
One of the only restaurants in Charlestown located on the water, Pier 6 offers cocktails with a fantastic view of Boston. Featuring a nautical theme, Pier 6 offers a large patio and bar on the first floor, along with a roof deck and full bar and dining room upstairs. The dining room features floor to ceiling windows, offering spectaular views of the water and city skyline. The restaurant offers a variety of seasonal cocktails, along with a nice selection of wines and local craft beers. They also offer a raw bar and full menu. During the warmer months, take advantage of the free water taxi over to their sister restaurant in East Boston, ReelHouse, where you can also enjoy cocktails on their large patio with great water views.
Legal Oysteria
10 City Square, Charlestown
Part of the Legal Sea Foods umbrella, Legal Oysteria is the company’s Italian coastal-seafood style concept. You won’t find a lobster roll or steamers here, but instead offerings like Italian-style mussels and Frito Misto, along with pasta and wood-fired pizzas. One of my favorite features of the Oysteria is their large wrap-around bar in the center of the restaurant. We often go sit at the bar for a drink or two before dinner, and they offer a nice selection of seasonal cocktails, along with a few different flights of wine (if you want to taste a variety of options). A full wine list and beer on tap round out their drink offerings. The Anjou Pear and Plymouth Cocktail are two of my seasonal fall favorites, and the Apple Sangria is delicious as well.
Best Places to Drink Beer in Charlestown
Brewer’s Fork
7 Moulton Street, Charlestown
Located a bit off the beaten track, you’re sure to find mostly locals enjoying beer (and likely some pizza) at Brewer’s Fork. With an outdoor beer garden in the warmer months, and a cozy bar that’s open year round, it’s one of the best places in the neighborhood for local, national and international craft beer. Their beer selection is carefully curated and rotates seasonally. You can generally find selections from the likes of Mystic, Night Shift, Jack’s Abby, along with other New England favorites like Allagash and Schillings. I highly recommend both the charcuterie board and the local cheese board to accompany your beer. If you want something a bit more filling, their wood-fired pizzas are some of the most popular in the neighborhood.
Monument Tavern
251 Main Street, Charlestown
Monument Tavern is still a relatively new addition to the neighborhood, having opened in January 2017. With the feel of a gastropub, Monument has a large wooden bar area that runs the entire length of the restaurant. They also have one of the best craft beer menus in the neighborhood. While their draught list is rotating, it often features hard-to-find selections from local brewers including Mystic Brewery in Chelsea and Idle Hands in Malden, as well as selections from Allagash, the Maine Beer Company and others. Their packaged beer selection also includes local favorites like Mayflower Brewing Company and Night Shift. If you want a snack to go along with your drink, the Roast Chicken Wings and the Pork & Spring Onion Dumplings are two solid bets.
Best Shops to Visit in Charlestown
Place & Gather
26 Common Street, Charlestown
Located in Winthrop Square, Place & Gather opened in 2017 as a boutique gift shop specializing in home decor, table settings and decorative accents. Selling items from many local Boston companies, the shop offers Noted Candles and Jill Rosenwald Ceramics, along with many Charlestown-themed items. I regularly see people in the neighborhood sporting Place & Gather’s signature hats with the Charlestown flag, and they also offer many items emblazoned with the neighborhood’s 02129 zip code.
The shop also offers a fun selection of colorful jewelry, and I’ve bought many pieces since it first opened its doors. Whether you’re looking for a personalized cutting board, Charlestown-themed cocktail napkins or a new set of earrings, Place & Gather is my go-to in the neighborhood. (And if you’re looking for fresh flowers and other local gift items, be sure to check out Place & Gather’s newly-opened sister store/flower shop Junebug, located at 211 Main Street in Charlestown).
Mockingbird Baby & Maternity
219 Main Street, Charlestown
Those will little ones will absolutely love the charming Mockingbird Baby & Maternity. Opened in 2014, the boutique offers a nice selection of maternity clothes from brands like Citizens of Humanity and Ingrid & Isabel, along with adorable clothes for children going up to size 4T. In addition to clothing, the store also offers nursery supplies, toys, books and games including Jellycat stuffed animals and Little Unicorn blankets, diaper bags, quilts and more. After visiting, it’s in a great location to pop next door to Zume’s Coffee House to pick up a latte and a pastry.
Best Places to Stay in Charlestown
Residence Inn Boston Harbor on Tudor Wharf
34-44 Charles River Ave, Charlestown
Located right on Tudor Wharf with spectacular views of the Zakim bridge and the North End, the Residence Inn Boston Harbor is one of the most conveniently-located places to stay in Charlestown. Just over the bridge from the North End, the all-suite hotel is right on the Freedom Trail and offers easy access to many of the historic attractions in Charlestown and Boston as a whole. Within walking distance of TD Garden, it’s a great spot to stay if you’re in town for a Celtics or Bruins game, or one of the many concerts that come to town each year.
Constitution Inn
Located within the historic Navy Yard, the Constitution Inn is one of the most affordable places to stay in the Boston area. With 147 rooms, the Inn is located on a picturesque cobblestone walkway. The hotel offers a complimentary shuttle to the North End. And it is also within easy walking distance of the USS Constitution and the Bunker Hill Monument. All guests can use the gym facilities at the adjoining YMCA (including the Y’s indoor swimming pool). The hotel also offers discounted rates for military personnel and their families.
What is your favorite spot in Charlestown? Let me know in the comments below!
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Categories: Charlestown, Destinations