Leather District

Intimacy is the name of the game at OFFSUIT, a tiny haunt tucked away in Boston’s Leather District. The night begins with a Catwoman-worthy prowl down Utica Street, where an unremarkable door serves as your portal into a world of refined drinking and dining. There are just 20 seats packed into this pint-sized watering hole, but OFFSUIT’s cocktail selection is by no means miniscule, featuring a wealth of perfectly crafted selections that include time-honored classics (Oaxaca old fashioneds and espresso martinis) alongside new creations like the Lounge Act, a blend of apple brandy, chamomile, falernum, curaçao, and Angostura bitters. Know before you go: Parties are restricted to four or fewer patrons, so roll shallow to this one.
How to book: Stop by for first come, first served seating.

3. Backbar

Just a few months shy of its 10th anniversary, this beloved bar made its debut in the heart of Somerville back in December of 2011, and the city’s cocktail scene has never been quite the same since. Backbar comes equipped with a cozy atmosphere adorned with stunning wall art, but it’s their avant-garde, quirky, and ultimately adorable cocktail theme that really endears this spot to local Massholes. Bears are the main topic around here—the animal kind, to be precise—and each cocktail is based around a beloved ursine figure, whether it’s an individual species, a pop culture icon, or the Chicago-based sports team.
How to book: Stop by for first come, first served seating.

5. Brick & Mortar
Central Square

We could not be more excited that our favorite upstairs speakeasy has finally reopened its clandestine doors. The cavernous, brick-walled space celebrates locally made spirits, seasonal ingredients, and a relaxed approach to imbibing. Keep it classy with a cognac and hibiscus-heavy Velvet Rope, or spring for a DTO—that’s Daiquiri Time Out, a certified group favorite complete with four rum-laden shots to really get the party started. Keeping with the sharing theme, Brick & Mortar also serves up a small yet mighty selection of tasty bar snacks, with pimento stuffed peppadew peppers, garlic bread, and deviled eggs all up for grabs.
How to book: Stop by for first come, first served seating.