3 Best Nightlife in Boston, Massachusetts

Watch the sun set over the Zakim Bridge as you peruse the extensive list of 34 rotating draughts, elite bottled beers, cask ale, draught wine, craft spirits, and custom cocktails (hello, Margarita Mondays). Located along the Freedom Trail at the end of the Charlestown Bridge, this watering hole is a favorite among locals to hang out and watch the game (expect crowds). Drinks like the Navy Yard Old Fashioned have ties to history, while their Bloody Mary flights and table mimosa with housemade purees are tasty options. The eclectic menu is full of tavern favorites like burgers, chicken wings, and flatbread pizzas, along with interesting twists like the Pitmaster Daily BBQ plate, moule frites, seafood bowls, and fried seafood.

At the end of your Charlestown trip, hit up this pub with a 50-plus beer list and classic pub fare with an Irish flare. With a backdrop of live music and traditional Irish seisiún (informal sessions), it's the spot to grab a lager with a snack of curry fries or calamari or satisfy a huge hunger with a shepherd's pie and the perfect Guinness pour. Weekend brunch Bloody Marys sit sidecar to traditional Irish breakfasts. Bonus points for the Airbnb right above the tavern that sleeps up to 16 (and has a pool table).

Nestled just 20 feet from the oceanfront, The Anchor is an open-air public gathering space, performing arts venue, and wine and beer garden. The two-story venue is full of swings, huge pillows set against stone terraces, lounge sets, and a grassy lawn for relaxing and sipping your cocktail. The menu offers items like air-fried cheese curds, jalapeno poppers, tacos, nachos, and chowder. The amphitheater hosts live music or movies seven nights a week, while other free events include comedy nights on Sunday, Monday salsa classes, waterfront wellness classes every day (think yoga, boot camp, Zumba), and live paint nights every Tuesday. In wintertime a dozen heated igloos and several fire pits keep things cozy.