Best Cocktail Bars in Massachusetts

Massachusetts drinks mostly in and around Boston, yet each town brings its own style. The best cocktail bars in Massachusetts start in Brookline, where Blossom Bar made the 2025 Spirited Awards regional Top 10 for Best U.S. Bar Team, and Merai on Harvard Street calls itself an elevated dive bar with a focus on Thai flavors. Equal Measure, just down the hall from the brasserie Eastern Standard, builds inventive drinks around seasonality and sustainability. Across the river in Harvard Square, The Longfellow Bar took over the historic Café Algiers space above Alden & Harlow. The Longfellow Bar opens at 5pm daily, and its tables can be booked through OpenTable. These are the bars we would start with.