Charlestown: Naval History, Fine Dining and the Oldest Pub in Massachusetts

A neighborhood guide to Charlestown from pub to battle monument to dockside

Few neighborhoods express new and old Boston as succinctly as Charlestown. If pockets of very fancy redevelopment point towards a gentrified future, the Bunker Hill Monument remains a fulcrum of the landscape rooted in the revolutionary, Brit-defying past—to walk around Charlestown is to wade through a history that is thick as molasses. If you fancy an ale where George Washington once drank, Charlestown can oblige (see below). What’s more, the influx of new money has not dented the neighborhood’s solid, hardscrabble Irish ‘Townie’ identity familiar to fans of movies such as “Mystic River” and “The Town.” All of which makes Charlestown an essential stop for any Boston visitor.

Clam chowder at Legal Oysteria


Popular local institution Legal Sea Foods offers a coastal Italian spin on its briny fare at Legal Oysteria, where a brick oven drives the menu and casual table-sharing is an option. Tangierino offers all sorts of Moroccan delectables, including marvelous tagines, and there’s a menu for hookahs and cigars to boot. Pier 6 offers outstanding waterfront dining, with incredible views back to the city and (in season) a spectacular roof deck; and excellent seasonal plates can be found at the Navy Yard Bistro, located a stone’s throw from the USS Constitution Museum.


The diminutive size and residential vibe of Charlestown sends retail hounds two short T stops north of Community College to Assembly Square, but anyone in search of eco-friendly toys and handmade art for kids should head over to Mockingbird on Main Street. In season (June-October), the Charlestown Farmers Market is well worth a browse every Wednesday 2-7 pm.

Brewer's Fork


The Warren Tavern draws a steady stream of history buffs and for good reason: It’s the oldest pub in Massachusetts and the list of past patrons includes Paul Revere and George Washington. The sense of history is as rich as the peppercorn sauce on the hearty baseball sirloin special. Monument Restaurant & Tavern sits comfortably in the territory where gastro meets bistro; and Brewer’s Fork offers one of the best selections of beer anywhere in the city—it’s also a solid choice for wood-fired pizza and fresh seafood too.


A perennial highlight of Charlestown is the USS  Constitution Museum, dedicated to preserving the stories and legend of the restored sailing vessel affectionately known as Old Ironsides. Check the website for details of events and exhibitions, from sea shanty singalongs to model ship shows. The Bunker Hill Museum, located across the grounds of the sky-piercing monument, will tell you everything you need to know about the first major battle of the American Revolution.

Annual model show