The Best Bars in Boston: From Dives and Speakeasies to Rooftops and Gay Bars

English and Irish settlers have influenced Boston’s booze scene for nearly 400 years, long ago establishing this beer-loving city’s popular pubs, countless dive bars and old-world speakeasies. But Beantown’s booming tech industry has also brought with it innovative craft-cocktail spots and luxurious rooftops sure to entice connoisseurs and mixologists from around the world. With so many options to choose from, Culture Trip has created a comprehensive list – broken down into helpful sections – of where the locals like to go.
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A craft brewery and a rooftop bar – does it get any better? Before opening a larger facility southwest of the city in Canton, Trillium’s Fort Point location was the original home of this local brewhouse. It opened a second and larger Fort Point location in 2018, complete with a delicious restaurant and rooftop bar. The decor is a modern and industrial interpretation of a New England farmhouse, as is its menu, with local ingredients creating the earthy, hoppy flavor profile of its classic IPAs and ales. Head out on the roof deck to sip your favorite beer and feel the sunshine on your shoulders, or watch the magic happen in the steel tanks inside.

At The Baseball Tavern, Fenway’s favorite rooftop bar, you can experience the magic of America’s oldest ballpark without the ticket price. Sit outside with a beer in hand and listen to the sounds of the bustling ballpark below. Watch the game live on the sports bar’s multiple flat-screen TVs while overlooking Fenway’s iconic Green Monster. Plus, when concert stars such as Bruce Springsteen and Billy Joel come into town to play at Fenway in the summertime, you’ll have the cheapest seats in the house to hear those songs you know and love (and belt them out with the rest of your new bar friends).

Known for its frozen margaritas and delicious Mexican food, Felipe’s is a fun, fast and friendly dining and drinking experience in the heart of Harvard Square. Beyond the savory tacos and mouthwatering margaritas, Felipe’s is best known for its festive roof deck, overlooking the bustling streets below. Grab your plate of nachos and claim your space on the patio. While it’s possible to order a drink downstairs with your food, head straight for the bar on the outdoor deck where you’ll be chilling in the sun all afternoon.

In Boston’s Seaport District, an up-and-coming neighborhood with award-winning eateries, craft breweries and some of the best roof-deck views in the city, lies Deck 12. Located at the top of YOTEL Boston, it features 270-degree panoramas of the city and Boston Harbor. Watch the city lights twinkle while sipping craft cocktails, or enjoy weekend brunch after having a fun night out on the town.

Pouring brews for Bostonians since 1795, Bell in Hand is America’s oldest tavern. Throughout its history, notable printers, politicians, local sailors and students have all enjoyed good food and great conversation over a pint at what became Boston’s most famous alehouse in the 18th century. Today, Bell in Hand is much the same in terms of atmosphere, with just a few more local beers on tap and live music on the weekends. Come in for a cold brew (or clever cocktail) and some hearty food, and stick around to watch the historic bar come to life, with a dance floor on the second level to continue the festivities well into the night.

Bostonians refer to this classic dive bar in Allston as the Sil’, and it’s been a neighborhood hotspot since about 1937. Don’t expect much at this no-frills watering hole. It’s a simple spot for city veterans and college kids alike, featuring cheap pitchers of PBR, cheaper drinks, free popcorn, pool and dartboards. Play a song on the old-school jukebox, and enjoy a night of nothing but low-budget booze and laughs with Boston residents. (However, beware of the few who may be slightly saltier than the popcorn.)

You’ll feel as though you’re walking the streets of Dublin when you pass by The Burren in Somerville’s Davis Square. A quick ride on the subway’s Red Line from downtown will get you within walking distance of this traditional Irish pub, named one of the 21 best in America by Thrillist. Enjoy a pint from the top Irish breweries, or try a local favorite. It features live Irish music in the front room seven days a week, so let the sound of the fiddle make your feet tap. Look at the pictures adorning the pub’s walls to truly grasp the local feel and learn a bit about the owners’ Irish roots. After 10pm, the backroom opens to all guests for on-stage entertainment, featuring hit songs of the ’80s, ’90s and today.

One of the best late-night speakeasy-style saloons in town, Lucky’s Lounge in Boston’s Seaport District is a perfect place to dance the night away. The discreet entrance and underground location add to the retro feel of this live music venue, with classic cocktails to bring you back to the days of Sinatra and swing dance. From Lucky’s Pimms Cup to the Paper Plane, there are many drink options to build up that liquid courage and get your feet tapping on the packed dance floor.

One of Boston’s classic British-inspired pubs, Cornwall’s is a family-owned bar where the locals go to congregate, drink beer and play games. This spot in Kenmore Square is known for its pool tables, dartboards and shelves of popular board games. Grab the Battleship or Monopoly board and a pint of local beer for a laid-back evening of good food and great company – a modern twist on the Revolutionary-era public house.

As the new kid on the gay-bar block, Cathedral Station has quickly become a Boston staple that welcomes everyone, creating a fun atmosphere for friends and families alike. Complete with a sunny outdoor patio with lots of seats, this local sports bar on the edge of the South End features a menu of classic bar food, including $0.50 wings on Mondays and Tuesdays – the perfect finger-licking snack to have while watching your favorite (Boston) sports teams. Stop by on the weekends for a little brunch on the patio, or come at night for a bit of evening entertainment courtesy of VJ Ryan Grow.

This landmark location in Boston’s Back Bay neighborhood is among the top gay bars and clubs in the city, and has been an LGBTQ community favorite for more than three decades. With exciting entertainment and risqué events every night of the week, it’s no wonder why. Mondays are drag bingo night, while Tuesdays are for trivia. A retro tea dance happens on Sundays, and there are also RuPaul’s Drag Race viewing parties, karaoke and much more. Dance the night away at one of the hottest parties in town on Friday and Saturday nights, and check out its line-up of cabaret singers in the Napoleon Room, including the popular Broadway sing-along show every Wednesday night. And if you sign up to be a Club Café VIP member, you can skip the lines and cover, get 20 percent off your dinner and attend exclusive wine tastings and cocktail receptions.

Located down (you guessed it) a back alley in the heart of Boston’s Downtown Crossing, The Alley Bar is a prime spot for a wild weekend night. Once you find it (located off a little pedestrian-only street), step inside for craft beers, bar bites and lots of dancing bears. On the first Saturday of the month, put on your best pair of briefs for the monthly UnderBear party, or tame the beast for a more casual night of trivia on Thursdays.

No, not the one-man cabaret act of “Just Jack” as seen in the late 1990s version of Will & Grace. Jacques Cabaret is a drag and cabaret bar where the queens of Boston show you all they’ve got. One of the city’s oldest continuously operating gay bars, Jacques is a small space with a big personality. Its location – tucked back in the residential Bay Village area – means there’s a strict midnight curfew (and all the dashing men and lovely ladies turn back into pumpkins or at least take off their make-up). Reservations are strongly recommended for the two Saturday night shows.

The scent of savory melted cheese and sweet maple bacon fills the air surrounding Roxy’s Grilled Cheese, the front for this secret speakeasy arcade bar (or barcade) in Cambridge. Find the freezer door in the back of the shop and step on through to the other side and another time. Old-school video games such as Pac-Man, Donkey Kong and Frogger line the walls and create makeshift aisles. Make a beeline for the bar, and peruse the list of playful adult beverages such as Ay Bay Bay Frozé and Carmen Sandiego that are sure to make you feel like a kid again. And that’s not even the best part – wait until you see which memorabilia-inspired drinkware your cocktail gets served in.

While not exactly a speakeasy, this wine bar in Union Square is quite the hidden gem. Rebel Rebel lies in Somerville’s charming Bow Market, an outdoor pop-up venue featuring seasonal shops and staple eateries. A self-proclaimed “no bullshit” wine bar, this female-owned business believes in the power of natural wine connecting us not only to farmers, but also to women and the planet. Featured wines regularly rotate on the blackboard above the cozy 20-seat bar space, and on some nights, you may even be lucky enough to meet the winemaker. The small space also has a patio – perfect for people-watching.

Downstairs at this South Boston hotspot, Capo’s Supper Club is reminiscent of a bygone era – a 1920s-style speakeasy bringing back the excitement of dinner and a show. Closed on Wednesdays, the Supper Club features rotating live music from Thursday through Saturday, with doors opening at 7:30pm sharp (reservations are strongly recommended). On Sundays, hear the soothing sounds of favorite Sinatra songs while enjoying home-made pizzas to share or entrées that will make your mouth water. Mondays feature local stand-up comedians who make the scene feel like an episode of The Marvelous Mrs Maisel, while classic cocktails and a robust vino list round out the speakeasy experience, with home-made gelato for a sweet treat to end the evening (or get it started).

At 567 Massachusetts Ave in Cambridge is an unmarked door next to Central Kitchen. If you enter the door and head upstairs, you’ll find dim lighting, a horseshoe-shaped industrial bar, exposed-brick walls and some excellent imbibing options. Brick and Mortar is a hip speakeasy that prides itself on high-end cocktails and knowledgeable mixologists who use uniquely flavored bitters, house-made syrups and lesser-known liqueurs.

Wink and Nod creates cordials, fresh juices and infusions in-house to guarantee the highest quality of freshness and expertise. This South End speakeasy-style bar also hosts a restaurant Incubator Program that features local chefs who take over the kitchen every six months, creating innovative dishes to pair with the drinks. Wink and Nod also has a monthly Scotch Club hosted at different nearby distilleries. There, attendees can taste exclusive flights of some of Scotland’s best whiskies and receive instructional lessons about the craft.