Getting to Know Your Neighborhood: Charlestown
Discover the charm and history of Boston’s oldest neighborhood
Located just north of the Charles River, Charlestown is Boston’s oldest neighborhood. Originally known as Mishawum, Charlestown proper was founded in 1628 and included what is now Woburn, Malden, Stoneham, and South Medford.
On June 17, 1775, Charlestown was the site of one of the most important battles of the Revolutionary War. American patriots delivered a devastating blow to the British army in the Battle of Bunker Hill. Nearly the entire town was destroyed during the battle and wasn’t rebuilt until after the war ended. The Bunker Hill Monument, which commemorates the colonists’ victory over the British, was erected between 1827 and 1843 and today marks the end of the Freedom Trail, comprising 16 sites that mark the city’s involvement in the Revolutionary War. In 1800, the Charlestown Navy Yard opened. A number of the most famous ships in the Civil War, including the USS Merrimack, were built there. Today, the Navy Yard is home to the USS Constitution—the oldest ship still afloat in the world—which was launched in 1797 and played a pivotal role in the War of 1812.
Charlestown became part of Boston in 1873, shortly after waves of Irish immigrants began settling there. For decades, it was one of the city’s largest Irish Catholic neighborhoods and, in the latter half of the 20th century, became known for ties to the Irish mob. By the late 1980s, Charlestown began undergoing a major gentrification process, and today the neighborhood is a mix of working-, middle-, and upper-middle class residents, drawn to its red brick townhouses and views of the water. Charming parks and squares dot the narrow streets, which are home to stylish shops, boutiques, and restaurants serving up top-tier local cuisine.
Located just across the river from the North End, Charlestown is connected to the northwest side of the peninsula by the Leonard P. Zakim Bunker Hill Memorial Bridge. Pedestrians can take the nearby North Washington Street Bridge to cross the river by foot. The neighborhood is closed off by East Cambridge and East Somerville on its western side. Visitors can enjoy spectacular views of the Boston skyline from dozens of vantage points along the waterfront.
We’ve put together a guide below to some of the best places to explore, eat, and shop when you next visit the neighborhood.
Paul Revere Park
North Washington Street
One of four parks created by the massive Big Dig construction project, which rerouted the central artery for I-93 below ground, the five-acre Paul Revere Park is located along the Charles River. The park opened in 1999 and features a large oval-shaped lawn and amphitheater, and a playground. It’s the perfect place for those seeking a scenic running route or a place to picnic. At dusk, you can watch the sun set behind the city skyline and take in breathtaking views of Boston and the stunning Leonard P. Zakim Bunker Hill Memorial Bridge, one of Boston’s most iconic structures, completed in 2003.
In 1985, archaeologists excavated the foundation of the 1629 meeting house where John Winthrop, the first governor of the Massachusetts Bay Colony, once lived and ruled in City Square. At that time, Charlestown was known as Boston, and modern-day Boston was called the Shawmut Peninsula. Winthrop proclaimed Boston to be “a city upon a hill.” That mission statement has since come to define America as a whole, a shining example of excellence to be followed by others. It was the first government building made in the colony before Winthrop relocated across the river with many of the other Puritan settlers. The structure later became the Three Cranes Tavern, a family-owned business that was in operation for over 140 years. Thanks to city archaeologists, park-goers can now see the outline of the 800-square-foot foundation—delineated by bricks—and learn more about how the neighborhood’s origins coincide with the beginning of a new city and colony.
Blackmoor Bar and Kitchen
One Chelsea St.
For a casual bite in the neighborhood, Blackmoor Bar and Kitchen is your first stop. It’s the perfect place to grab a burger. Start with a warm German salted pretzel and a sauce of Vermont cheese fondue, honey, and grain mustard. You won’t want to miss the restaurant’s delicious wings, which are just 50 cents on Mondays, from 5 to 10 pm, with the purchase of a burger or a sandwich. Try the fish and chips if you’re seeking a classic tavern dish. Come by on the weekend for an eclectic brunch menu, including breakfast poutine and fried chicken and waffles. And beer lovers will enjoy the rotating selection of over three dozen draughts and bottled beer.
2 Pleasant St.
Want to get a bite at a restaurant once frequented by Paul Revere and George Washington? Look no further than Warren Tavern, which opened circa 1780, making it Massachusetts’ oldest tavern—and one of the oldest in the nation. The atmosphere is cozy, and the restaurant’s several large-screen TVs make it the perfect place to watch big sports events. The tavern boasts that it serves “the best” New England clam chowder found anywhere (one bite and you’ll likely agree). The fish and chips, made with fresh haddock, is another quintessential New England meal.
St. Mary–St. Catherine of Siena Church
55 Warren St.
No architecture tour of Charlestown would be complete without a visit to St. Mary-St. Catherine of Siena Church. Originally known as St. Mary’s, the first church building opened in 1828. At the time, it was only the second Catholic parish in Massachusetts. A newer church, still in use today, opened in 1889. The church’s soaring Romanesque interior features stained glass windows by Franz Mayer & Co. and a hammer-beam oak ceiling decorated with angels, carved by Patrick Keely, a prominent Irish Catholic architect who designed more than 600 churches across the country. The church served as a central place of worship for the many Irish immigrants who began settling in Charlestown starting in the mid-19th century. In 2007, St. Mary’s merged with another Charlestown parish, St. Catherine of Siena, hence its current name.
John Harvard Mall
This mall, adjacent to City Square Park, stands on the site of English-born minister John Harvard’s house. On his deathbed in 1636, he donated a large portion of his estate and his voluminous book collection to what is now Harvard University, making him its most prominent early benefactor. In gratitude, the school’s trustees named the University in his honor. Today, majestic trees surround red brick stairs and sturdy benches, making this park the perfect refuge for those seeking peace and quiet. Take a loop around the park, and you’ll discover several placards that reveal more about the history of John Harvard’s life and the history of Charlestown. The main entrance is located on Main Street, and the entrance at the top of the steps leads the way to the Bunker Hill Monument.
211 Main St.
This florist and boutique sells exquisite flowers and unique, handcrafted gifts and jewelry. The shop’s collection of Boston-themed clothing makes for great holiday gifts for friends and family. You’ll also find seasonal decor, including ornaments, wreaths and evergreens, candles, and stockings designed to get you into the holiday spirit. If that’s not enough, there’s also jewelry, hats, scarves, and homewares, including frames, vases, trays, lamps, pillows, and local prints to brighten up your home.
Zume’s Coffee House
221 Main St.
Pronounced “Zoomies,” this coffee house offers a warm, modern ambience and serves up a wide range of drinks. Their espresso menu is especially impressive. If you’re looking for a coffee alternative, try the flavorful mint matcha tea latte. You’ll also find a mouthwatering assortment of freshly baked goods, including scones and buttery croissants. Comfy chairs and plenty of tables make it the ideal place to get some studying done or catch up with friends.
On Again Consignment
223 Main St.
Love thrifting? Then you’ll want to check out this boutique consignment shop specializing in luxury retailers. Shoppers will find all the hottest high-end brands, including Gucci, Chanel, Louis Vuitton, and Burberry. From purses and wallets to boots and scarves, you’ll find well-made, gently worn clothing and accessories to enhance your wardrobe.
251 Main St.
Renowned for serving up innovative comfort food, Monument Tavern is a Charlestown institution. The red brick walls and high ceilings make the space feel expansive and open. The menu ranges from Italian classics to tacos to dumplings. The wood-fired pizzas and chicken wings and braised short ribs are especially popular. Monument also hosts a popular weekend brunch. Don’t miss the pumpkin cheesecake french toast and fried chicken biscuit.
Bunker Hill Monument
31 Monument Sq.
Commemorating the first major battle of the American Revolution, the Bunker Hill Monument memorializes the battle fought in Charlestown on the afternoon of June 17, 1775, when British troops advanced towards the colonist troops’ defenses erected along the Charlestown peninsula. Legend has it that Colonel William Prescott instructed his troops not to fire “until you see the whites of their eyes.” Today, scholars believe no such order was ever issued, but the battle symbolized the grit and determination of American colonists in their struggle against the British. And while they lost the battle, they were able to inflict heavy casualties among the British. One of the nation’s oldest monuments, completed in 1843, it took nearly two decades to complete.
The 221-foot-tall granite obelisk (the granite was transported to Charlestown from a quarry in Quincy) is one of the most recognizable landmarks in Boston, and offers sweeping views of the city and the Boston Harbor for those willing to climb all 294 stairs. (Note: the monument is only open to 20 visitors at a time, so you may have to wait in line a bit.) The memorial’s name is a misnomer, as the monument sits atop Breed’s Hill, where most of the battle actually occurred. Bunker Hill is about 700 yards away and had only a peripheral role in the fighting. The monument underwent a major renovation, completed in 2007, which included better lighting and handicap accessibility improvements. Today, the site, part of Boston National Historic Park, is administered by the National Park Service.
Bunker Hill Museum
43 Monument Square
In the former Charlestown branch of the Boston Public Library, this museum—also part of Boston National Historic Park and operated by the National Park Service—opened in 2007 and tells the Battle of Bunker Hill story through a series of exhibitions and dioramas. A visitor’s center on the main floor provides brochures to Boston National Historic Museum, the Freedom Trail, Bunker Hill, and the Charlestown Navy Yard, plus free tickets to climb the Bunker Hill Monument across the street. There is also a book and souvenir store, the largest found in any of the park’s visitor centers. Exhibitions on the first floor focus on the history of Charlestown, while the upper floor covers the Battle of Bunker Hill and includes a number of interesting artifacts. There’s also a model of the battle with toy soldiers, with a short audio presentation about the battle. The museum is open most days of the year.
Building 22, Charlestown Navy Yard
The world’s oldest commissioned warship still afloat, the USS Constitution, also known as “Old Ironsides,” was one of the first six frigates launched in 1797 to make up the fledgling US Navy. The ship initially protected the Eastern Seaboard from pirate attacks and was involved in engagements with pirates off the Barbary Coast in the Mediterranean. The vessel earned her nickname during the War of 1812, after cannon fire from enemy ships was unable to penetrate her strong oak hull. Today, visitors can board the ship, which is inside Boston National Historic Park, as part of the Charlestown Navy Yard. Free tours are offered daily, Wednesday through Sunday, 10 am to 4 pm, and a virtual tour can be viewed here. Crew members are on hand to answer questions about the boat’s storied history. Note: all visitors 18-plus must present a valid photo ID to board the ship.
USS Constitution Museum
Building 22, Charlestown Navy Yard
The USS Constitution Museum “serves as the memory and education voice of the USS Constitution” by providing informative and engaging experiences for visitors of all ages. Permanent exhibitions document the ship’s history from forest to frigate, and the significant upkeep it took to keep “Old Ironsides” looking new. Preserved archival records, photographs, paintings, and letters chronicle the ship’s incredible history. Interactive activities let visitors design their own frigate, experience life at sea for themselves, and view a timelapse of the ship’s extensive 2015–2017 restoration. Just across the pier from the USS Constitution, the museum also hosts ongoing special exhibitions and attracts more than 350,000 visitors a year, making it one of Boston’s most popular museums.
USS Cassin Young
198 3rd St.
In the Charlestown Navy Yard is another warship, the USS Cassin Young, a large destroyer that had an active role during World War II. The ship is named for Captain Cassin Young, who was awarded the Medal of Honor for heroic action during the attack of Pearl Harbor and was later killed at Guadalcanal in 1942. Fletcher-class destroyers had a key role in fighting air, land, and sea battles in the Pacific theater during the war and were designed for speed and versatility. The all-purpose ships carried both anti-aircraft guns and torpedoes, as well as a full crew. The USS Cassin Young saw significant action in the Pacific, including during the Allied victory at Okinawa, and later survived a single kamikaze attack directly to her starboard. Since the war’s end, the ship has undergone major repairs, and today is open seasonally to the public for top-deck access and free, below-deck guided tours conducted by the National Park Service.
1 Shipyard Park
Boston magazine named The Anchor the “Best Beer and Wine Garden” in Boston in 2021. The beer and wine menu is comprehensive, designed to pair well with a menu of small bites, including tropical pulled pork sliders. Try a boozy cider or a flavored margarita for a tasty treat. Those looking for something nonalcoholic can enjoy a soothing hot chocolate or hot tea. More than just a beer garden, the vibrant public space is open to all ages and hosts more than 300 programs and events each year, including a waterfront wellness series, trivia and movie nights, and more. The Anchor also offers a range of live music events, from mellow acoustic performances to spirited reggae bands.
Waverly Kitchen & Bar
231 Bunker Hill St.
Centrally located near the Bunker Hill Monument and the Freedom Trail, Waverly Kitchen & Bar serves breakfast, lunch, and dinner seven days a week. Enjoy your meal in their comfortable dining room, or grab a coffee and lunch to go. Try the eggplant parmesan stack with herbed whipped ricotta and smoked mozzarella for dinner, or the buttermilk pancakes with honey butter and Vermont maple syrup for breakfast.
54 High St.
This fashion and lifestyle boutique offers a carefully curated collection of clothing, jewelry, home accessories, and clean beauty products. The store hosts charitable events and partnerships to give back to the community. If you can’t make it to the store, you can browse their online collection here. Slate also operates a seasonal store on Martha’s Vineyard.
7 Moulton St.
If you’re looking for a place to enjoy some unforgettable pizza, draft beers, cider, and cocktails. Outdoor dining is available during warm-weather months on the restaurant’s patio; the interior offers a rustic, laid-back vibe. You’ll find standard cheese and sausage pizzas, but Brewer’s Fork is really known for their creative pizza creations like the Freebird (featuring smoked chicken, pickled collard greens, and mozzarella) or the Johnny Appleseed with honeycrisp apple butter, sharp cheddar, and bacon.
1 6th St.
Dovetail offers a sit-down restaurant featuring a range of snacks and sides, small plates—the persimmon salad with cucumber, feta cheese, watercress, and a tamarind dressing is outstanding—and entrees ranging from Atlantic halibut to pork Milanese. It also sells salads, soups, and sandwiches to go. Try the restaurant’s campanelle with mushrooms, baby kale, porcini butter, marsala, and sage, or the spicy Italian sandwich made with charcuterie genoa, hot pepper relish, and lettuce. Dovetail is open for lunch and dinner seven days a week, and for brunch on weekends.
1 8th St.
Pier 6 is one of Boston’s premier waterfront dining destinations. The restaurant offers sweeping panoramic views of the Financial District and downtown Boston—and its fish is among the freshest you’ll find anywhere in the city. Oysters and fried calamari make for great appetizers, and the baked halibut and Atlantic salmon are outstanding entrées. Pier 6 also serves up a great weekend brunch that will give a big boost to your Instagram feed. The one-of-a-kind Maine omelet is served with lobster, spinach, hollandaise, English muffin, home fries, and a side salad. The “crab benny,” a New England take on eggs benedict, includes poached eggs, crab, home fries, hollandaise, and a side salad. The prices are on the steep side, but it’s a great place to take your parents (assuming they’re footing the bill).
Getting there: Take a Green Line MBTA trolley to Government Center. Walk down North Washington Street and cross over the North Washington Street Bridge to City Square. Or take an MBTA Orange Line train to Sullivan Square. By bus, hop on the #93 at Congress St @ Haymarket Station to Chelsea St @ Warren St.