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How to spend a perfect day in Charlestown
"The relationship and intersection of the old and the new is what Charlestown is really known for.”
Just north of the Charles River is Boston’s oldest neighborhood, Charlestown.
The charming area has a striking mix of old roots that date back to the early 1600s and the new residents that continue to build their lives in one of the most family-friendly neighborhoods in the city.
“I feel like the story of Charlestown is that there is always a baby on the way,” laughed Amanda Zettel as she checked on her neighbor, a brand new mom. “A lot of people call it Boston’s suburb.”
Zettel moved to the neighborhood from the South End to flip a house with her husband. She figured if Charlestown was not the right fit, they would sell their remodeled home after two years for a new adventure. More than a decade later, she finds herself the president of the Charlestown Preservation Society where she works to protect the historic architecture while growing the community.
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“I fell in love with Charlestown,” said Zettel. “There are these moments of juxtaposition between the old neighborhood and the new Boston skyline. The relationship and intersection of the old and the new is what Charlestown is really known for.”
In addition to her position leading the Charlestown Preservation Society, Zettel is an interior designer with over twenty years of experience. Her passion for well-crafted, unique architecture made Charlestown easy to call home quickly as a self-proclaimed “history and architecture nerd.”
The Charlestown Preservation Society is one of a few organizations that work to preserve historic Charlestown while encouraging sustainable development. It was established in 1967 during the urban renewal projects that reshaped Boston and changed residential neighborhoods like the West End.
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“Right after the city cleared the West End, the city had their sights set on Charlestown,” said Zettel. “The neighborhood fought back and said absolutely not.”
Rather than face total demolition, the CPS identified the most historic buildings in the area and negotiated with the city of Boston to maintain their neighborhood.
The town is gearing up for the 250th anniversary of the Battle of Bunker Hill this summer where they will commemorate its significance in the Revolutionary War and American independence. While every anniversary has a parade and reenactments down Bunker Hill Street, this year is especially exciting for longtime residents.
“It is going to be a gigantic festival and we are already talking about how to showcase all of the restaurants and retail that are local,” said Zettel.
Ahead, here’s how Zettel would spend her perfect day in Charlestown.
Morning | Afternoon | Evening | Map | Share your perfect day in Boston
Morning in Charlestown
Amanda enjoys stopping in at Waverly’s Kitchen & Bar (229 Bunker Hill St.) to start off her mornings. She enjoys finding a spot at their bar and grabbing a warm drink to start off the day. Here, she can open her laptop and get some work out of the way or meet up with friends. The spot on historic Bunker Hill Street serves is a middle ground between upscale dining and quick, friendly service.
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If she is feeling like a quicker breakfast is the move for a busy day, she will look towards new baker La Saison (221 Main St.) where she recommends the Pumpkin Orange Peel cookies and chocolate croissants.
“Charlestown is really compact and I don’t have a car but that doesn’t stop me from going all over,” said Amanda. The heart of Charlestown is only one square mile, so all of the best bakeries and shops are easily accessible.
After grabbing a morning coffee and pastry, Amanda enjoys walking around to shop at some of her favorite local stores.
Unlike many other areas of Boston, Charlestown primarily has small businesses.
First up is Kaybea Collection (1 Monument Ave.), a curated women’s clothing and accessory shop. At the boutique, owner Kayla King greets Amanda with new signature styles.
As a member of the Charlestown Business Alliance, Kayla enjoys collaborating with other organizations and businesses to drive the small businesses of Charlestown forward.
“It’s community over competition,” said Kayla.
In addition to Kaybea Collection, Amanda loves to pop into Slate (54 High St.), an upscale women’s clothing boutique focused on sustainable women-owned brands, and Place and Gather (26 Common St.), a charming New England souvenir and home gift shop.
At Place & Gather, Amanda points out that she thinks Charlestown is the only Boston neighborhood to have its own flag and prides itself on the town slogan of “Boston but better.”
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“Any time I have a birthday coming up, I have to head there,” said Amanda.
When the sun is shining, Amanda can usually spot plenty of kids after school using the Training Field, also known as Winthrop Square, as a race track. The land was originally for military purposes but has been transformed multiple times to be residential. While you sit on a bench taking in the Charlestown architecture along the Freedom Trail, you can catch the Bunker Hill Monument (Monument Square) and a smattering of cherry blossom trees in the spring.
Afternoon in Charlestown
After working up an appetite shopping, Amanda enjoys heading to the Navy Yard to grab a sandwich at Dovetail (1 6th St.) and walking to the Charlestown Navy Yard (1st Ave. & 3rd St.) to eat outside.
“The best is to sit by the water. It feels like you are on vacation in the summertime,” said Amanda.
Also in the Navy Yard is the USS Constitution (1 Constitution Rd.) and its accompanying free museum. Every afternoon as the sun sets, everyone in Charlestown can hear the cannons go off. American sailors live in the Yard to maintain the historic ship.
Charlestown has MBTA stops along the Orange Line, including Community College and Sullivan Square, and a ferry line directly from downtown near the New England Aquarium. From the Navy Yard, Amanda can hop on a quick ferry for a beautiful view and easy transportation.
For a lunch-spot with a lot of history, Amanda recommends heading to Warren Tavern (2 Pleasant St.), the oldest tavern in Massachusetts to dine like George Washington. Up the street is also Deacon Larkin’s House (2 Freedom Trail), a patriot known for giving Paul Revere the horse he used for the midnight ride to Lexington and Concord.
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If you are looking for a more modern space, Amanda recommends the “industrial-feeling” Brewer’s Fork (7 Moulton St.) where there are delicious pizzas, or Blackmoor Bar and Grill (1 Chelsea St.), especially in the summer when an impressive beer garden is in full swing.
For the rest of the afternoon, Amanda recommends walking across the neighborhood looking at the historical sites. Charlestown is home to nine of the 50 oldest buildings in Boston.
While the entire area is charming, many buildings have been certified historic from the Charlestown Preservation Society and are marked with plaques at their bases. Modern homes are dubbed infill homes and urged to maintain the same style as the historic buildings but still be creative.
“We encourage new design that still fits in,” said Amanda.
One “perfect” example of restoration according to Amanda and honoring traditional architecture in Charlestown is Memorial Hall (14 Green St.), a 1700s structure originally built to house Samuel Dexter, an attorney and congressman, and was purchased by Abraham Lincoln Post 11 of the Grand Army of the Republic. The advocacy group converted it to a social and meeting hall – two functions it still houses today. The building has been refurbished with handmade detailing to mimic its original form.
Just up the street from Memorial Hall is Engine 50 (34 Winthrop St.), or the People’s Firehouse. In the 1980s, the City threatened to tear down the building and locals occupied the firehouse in protest. Individuals handcuffed themselves to fire trucks and refused to leave until it was reactivated shortly after, according to Amanda.
Evening in Charlestown
Charlestown also has refined dining options that are suited for a night out, according to Amanda. One of her favorite spots is Prima Italian Steakhouse (10 City Square), a decadent restaurant with two secret “speakeasy” rooms in the back.
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“I went to the most incredible 40th birthday party here and they rented out the Rose Room,” said Amanda.
After the night at Prima, Amanda recommends walking through City Square Park nearby and noticing the remains of John Winthrop’s Great House.
If you have not gotten enough of the sparkling water near the Navy Yard, Amanda also recommends heading back to Pier 6 (1 8th St.). At the rooftop, there are panoramic Boston-skyline views that do not quit.
After an active day, Amanda also loves to entertain guests with fresh food in her home. She loves to grab some fresh noodles from Main Street Pasta and Wine (40 Main St.) to be coated in her husband’s homemade tomato sauce.
Often, Amanda will end nice days with a nightcap at the outdoor lounge area The Anchor (1 Shipyard Park) where she joins friends for outdoor music, beverages with their puppies especially in the warmer weather. In the coming weeks, the space will be a great spot to catch a Celtics game or listen to live music.
“I can be downtown in seven minutes after a day in Charlestown since the reality is we live right next door,” said Amanda. “But I have to find excuses to leave because this neighborhood has everything that I could even need.”
Map: How to spend the perfect day in Charlestown 📍
Correction: A previous version of this story incorrectly stated there are no MBTA stations in the neighborhood. There are stations along the Orange Line and several MBTA bus stops. Boston.com regrets the errors.
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