Like a Local
Quirky, under-the-radar highlights only a local could recommend.
Often missed by tourists and locals alike, Castle Island in South Boston is a great place to stroll along Boston Harbor. The site of an old armory, it is a 22-acre “land-bound” island (meaning it was connected to the mainland by a narrow strip of land in 1928) home to a paved walkway and a shoreline string of parks and beaches. Bring a picnic, or hit the snack bar that serves burgers, fries, clam strips, and ice cream.
Bunker Hill Monument
Boston is a city filled with landmarks, but one of the less touristy spots is this 221-foot-tall granite obelisk in Charlestown that marks the site of the first major battle of the American Revolution. While you can hoof the 294 steps to the top to see the unparalleled view of the city, locals prefer to sprawl out on the lush green lawn to soak up the sun with a picnic or dive into a book.
Roped off behind the bar of JM Curley in Downtown Crossing, this secluded, darkly lit 20-seat chophouse is marked only by a small gold placard that reads “Bogies” and the art deco signage that proclaims “Adults only. Please no cell phone use.” Inside, expect decadent cuts of steak, caviar service, and à la carte build-your-own martini menu.
One of Boston’s oldest restaurants, having opened in 1885, this local gem on a dead-end street in Downtown Crossing features a comfort food menu that takes cues from French, Italian, and straight-up New England. Locals swear its “Sunday Gravy” is the best pasta dish you’ll get in all of Boston.