Neighborhood Guide: An Afternoon in Charlestown
When:
Wednesday, Jan 01, 2025 12:00p -
Wednesday, Dec 31, 2025 6:00p
Wednesday, Jan 01, 2025 12:00p -
Wednesday, Dec 31, 2025 6:00p
Where:
Charlestown
Charlestown
Charlestown, MA 02129
Admission:
$varies
Categories:
Date Idea, Drinks, Food, History, Photoworthy, Shopping
Nestled on the banks of the Boston Harbor, Charlestown is a vibrant neighborhood where centuries of American history meet modern urban charm. As the oldest neighborhood in Boston, Charlestown is home to iconic landmarks like the Bunker Hill Monument and the USS Constitution, alongside charming brick row houses, cozy pubs, and a thriving waterfront. Here are our recommendations for an afternoon exploring the neighborhood:
by Nicole Rosania
1) Brunch at Waverly Kitchen & Bar
Located in the heart of Charlestown, Boston, just steps away from the Bunker Hill Monument and the Freedom Trail, Waverly Charlestown is a neighborhood restaurant that serves breakfast, lunch, and dinner seven days a week. Join us for a legendary brunch, dinner, and cocktails in our cozy dining room, or grab coffee and lunch on the go.
2) See the Zakim Bridge from Pleasant Street
Pleasant Street lives up to its name—a peaceful, tree-lined stretch tucked into the heart of Charlestown that captures the neighborhood’s timeless appeal.
Lined with classic brick townhouses, historic wooden homes, and the occasional hidden garden, Pleasant Street feels like a walk back in time. You can see the city skyline and the Zakim Bridge from the hill. Plus, the Bunker Hill Monument is just one block away!
3) Shop at Junebug
There are many cute boutiques around Charlestown, but Junebug is our favorite! Stop here for gifts, home decor, and floral arrangements.
The USS Constitution, also known as “Old Ironsides,” is the world’s oldest commissioned warship still afloat and a symbol of early American naval power. Docked at the Charlestown Navy Yard, it offers visitors a chance to explore a piece of living history and learn about its legendary role in the War of 1812.
5) Dinner & Drinks at The Monument
Cozy neighborhood restaurant perfect for drinks, appetizers, or dinner to cap your afternoon in Charlestown! Plus, The Monument has $1 oyster deals!
