I love a hidden gem. There’s nothing like unlocking a treasure when you least expect it. My summer internship led me to stumble upon one of Boston’s greatest hidden gems: Charlestown, Mass.
Nestled above the Charles River and upper Boston Harbor, historic Charlestown is full of contagious patriotism, charm, and seaside tranquility. Only a five-minute walk from the North End, the Charlestown Marina looks out onto the lights of the city skyline and monumental Zakim Bridge. Red brick sidewalks line quaint streets that surround the neighborhood’s hard-to-miss landmark: the Bunker Hill Monument, which is the culmination of Boston’s Freedom Trail. One visit to Charlestown and you’ll understand why I think this area is a nonnegotiable part of any Boston bucket list!
Getting to Charlestown
Perhaps the biggest downside of visiting Charlestown is the commute from Boston College. While a 40-minute T ride may seem daunting, three green line stops—Boston College, Cleveland Circle, and Reservoir—provide direct transportation to North Station. The ride travels under Fenway Park, Newbury Street, and the Boston Common, and it offers you time to read a book, listen to a podcast, catch up with a friend, or simply observe the day-to-day occurrences of the city. Make the most of your MBTA riding experience!
As you get off at North Station, take in the hubbub of TD Garden, home of the Boston Celtics and Bruins and a frequent venue for concerts. Walk one block toward the water and Charlestown lies over the harbor—you can see the marina boats swaying in the distance. Follow the red brick road of the Freedom Trail along the North Washington Street Bridge, or take the “scenic route” and cross the Charles River Dam.
While calling an Uber or driving a car are much faster ways to get into the city, both can be costly—parking options in Charlestown are expensive and limited. Bring along a friend to fill the commute with conversation or listen to a song that gives main character energy, making the ride all the more exciting.
A Historical Haven
Charlestown was established in 1628 as a Puritan colony and is two years older than the City of Boston. Once home to John Endecott, the first governor of Massachusetts Bay Colony, and John Winthrop, the Puritan leader famous for coining the colony “the city on hill,” the town gained recognition after hosting one of the major battles of the American Revolution, the Battle of Bunker Hill, in June 1775.
Charlestown’s history extends far beyond this turning-point battle. Throughout the 19th and 20th centuries, the Charlestown Navy Yard was one of the nation’s prominent shipbuilding facilities. While no longer a manufacturing site, the Navy Yard memorializes its history through several ships that are still maintained. To explore this history, step onto and wander the USS Constitution, which is the oldest warship still afloat. Keep following the red brick road of the Freedom Trail to the Bunker Hill Monument. Climb its 294 steps and celebrate your victorious trek with gorgeous views of the Boston skyline and inner harbor.
Monumental Eats
Charlestown isn’t short on culinary delights. Begin your morning with a coffee from Mister Q. Cafe. For lunch, stop by Dovetail—the restaurant’s fresh sandwiches are some of the best I’ve had in Boston!
Given the town’s proximity to the North End, Charlestown has numerous pizzerias of its own. Stop by Johnny Pomodoro for a Sicilian slice or Brewer’s Fork for a wood-fired pie.
To quench your thirst, grab a pint at Boston’s oldest watering hole, Warren Tavern, which first opened its doors in 1780. For drinks with a view, sip on nautical-inspired cocktails at The Anchor or Blackmoor Bar and Kitchen, or take your experience to the next level with a glass of wine on the upper deck of Pier 6.
Revolutionary Shopping
Small businesses bring the Charlestown community to life. Many of the shopkeepers are close friends with one another and frequently collaborate to promote the other’s business. Place & Gather is a prepster’s paradise of home decor, jewelry, and lifestyle goods that boast Charlestown pride—it frequently collaborates with sister store Junebug, which is a florist known for its cheerful pink exterior.
Contemporary boutiques like Slate and Kaybea Collection run on the pricier side but carry investment pieces you’ll wear and use for years. Picture flair denim jeans, floral flowy dresses, and unique accessories like sling purses and chambray hats.
If you stroll through Main Street on Wednesday afternoon, you’ll catch the farmer’s market! Stores like Main Street Pasta & Wine set up tables and many local artisans display their work along the sidewalks. My favorite part is the fresh produce that is perfect to pick up for a midday snack or take home and use in a refreshing meal.
From Sea To Shining City
The Charlestown Marina gets lost in the shadows of Long Wharf and Fan Pier, but it boasts just as good, if not better, views of the Boston skyline. It’s an underrated oasis of sea breeze and serenity. Breathe in the salty air, listen to the sway of the boats in the water, and soak in rays of sun as you stroll along the peaceful conclusion of the Boston Harborwalk.
Take a Scenic Stroll
One of the best ways to take in the charm of Charlestown is to simply walk around. The narrow streets form a quaint neighborhood rich in charm and immediacy. Mothers push their children in strollers while young professionals cruise by on bikes, commuting into the city.
Get lost in rows of townhouses basked in brick and colorful shingles, stroll through a picket-fenced park, and admire the bright hydrangeas that peak in the summer. You can feel the pride from the city bursting from the care of each doorway—Charlestown even has its own flag, which seems to be waving from a home on every block.
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