112 Best Bars in Massachusetts, USA

You don't have to be a hotel guest to enjoy skyline and harbor views at this seventh-story rooftop bar. The vibe is lively during warmer months, as you might expect, with people crowded on cabana-style bench seating and the occasional fire pit. Premium classic cocktails and seasonal sips (think a frozen lychee "frosee"), and really tasty food mean that you'll go home satisfied. Stop by in the winter for a "snow globe" experience inside heated, transparent geodesic domes.

Cocktails are the star of the show here, and not classic ones at that, but there's also a great selection of local draft beers and a few wines by the glass. There are also a handful of snacks to counteract the alcohol. This place is popular, so reservations are strongly recommended.

Aptly overlooking its namesake's statue, the 15,000-square-foot Sam Adams Boston Taproom boasts three floors, including a rooftop terrace with views over Faneuil Hall. Drink like a local, by choosing a flight of innovative styles and rotating experimental beers from the nanobrewery as well as fan favorites such as Boston Lager and seasonal brews like Summer Ale. Suds occasionally sit secondary to fun events like yoga, speed dating, live music, drag shows, and comedy nights. Thursday translates to newly introduced drafts on the menu.

Follow the retro neon sign to the music scene you've been waiting for. Bringing a long-awaited sophisticated rock music and dining venue to Harvard Square, The Sinclair's adventurous, near-nightly lineup of indie rock—with enticing flings into world, electronica, and jazz—often sells out. Its adjacent but quite separate restaurant and bar, with wanderlusty train and highway decor, a serious beverage list, creative mixology, and cuisine inspired by regional Americana at on-site Brato, is proving to be a winning formula. Accommodating 500, here's a party made to order for transient, academic, and streetwise grown-ups.

The crowd spilling through French doors onto the sidewalk café in warm weather consists of trendy cosmopolitans, fun-loving professionals, local sports celebs, and scenesters who have flocked to the contemporary spot for decades. The sophisticated jazz-rock soundtrack remains at a civilized volume as you dine, sip, and people-watch. Order any of the martinis that earn a solid rep among the locals, and follow with a brick-oven pizza off their late-night menu.

This historic-style ship sidles up to an East Boston pier and features outdoor drinking, games like corn hole, live music, and more alfresco fun. You can also book a private lounge. The unique destination does offer food in the form of raw oysters, pizza, tacos, and fried seafood, plus there are a number of food trucks that park on-site. Drinks are slightly overpriced, but let's be honest: you're paying for the view. If you happen to be dining in the area, there's a free shuttle to the ship from local restaurants on the weekends.

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 music 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.

When it comes to craft beer, a lot of Bostonians get excited about Trillium. Do as the locals do and quench your thirst in the ever-crowded ground-level taproom or sit for a quieter meal upstairs to enjoy a small menu of American fare that's meant to keep you reaching for more. Taps rotate with seasonal and standard Trillium beers, including ciders, sours, and IPAs. It's family-friendly during the day, with live music and trivia at night during the week. There's a fantastic roof deck, which is open seasonally.

Inventive cocktails wash down Southern comfort grub at this hip, retro joint packed with a younger crowd. The original drinks are just that—original—with concoctions like the Rockin' Chair (black-tea-infused bourbon, canton ginger cognac, and lemon) and the Fallen Angel (a spicy mango margarita with a barbecue-dusted rim). Their buttermilk fried chicken is well loved, and the mac and cheese with Ritz crackers and hot dogs is your new guilty pleasure.

Tucked under the Staypineapple Boston inn, this gay bar is popular with the local after-work crowd, who enjoy live performances from local artists and apps like nachos and chicken fingers. Casually dressed locals drop by for the large beer list and classic breakfast dishes during the hopping weekend brunches starting at noon, which feature long, tall mimosas, and bloodies.

This new complex has live music, lit up bowling for $35--$45 per lane, TVs for the big game, and more. Drinks are social, including the four- to six-person cocktail "coolers," which is probably why the entire place is 21 and older after 7 pm. Snacks are fun noshes, such as waffle fries, grilled burgers, nachos, and a giant baked chocolate chip cookie.

Popular arcade games, pinball, and '80s pop culture provide the entertainment at this nightspot, but no one under 21 is allowed after 7 pm. The fun extends to weekly theme nights, including free play and Super Smash Bros. tournaments. The food is decent but nothing special—although there are milk shakes.

A resident DJ curates the music at the W's chic lounge and bar. Large-format drinks that serve four people are fun to dive into, alongside some elevated snacks, flatbreads, and a few dinner platings. Crowds tend to gather early in the evening and go to about midnight before making a move elsewhere.

Recently named one of the most beautiful restaurants in America by People magazine, this hidden-away gem is all about escaping with a tropical tiki. Drinks include the Scorpion Bowl, made with Appleton estate rum, lemon, mango, orange, pineapple, and hibiscus grenadine, as well as the Jungle Bird, a marriage of two types of rum, Campari, pineapple and lime juices, and demerara syrup. The menu offers up Asian American bites, such as a pupu platter that can also be made vegan, short rib lo mein, and Aloha sliders.

This spacious, popular venue connected with Paradise offers bands nightly, some open to all ages, often double bills.

The upstairs pub–-dismantled in England, shipped to Boston, and reassembled–-later became the inspiration for the now-classic TV series Cheers. Enjoy a quality burger at the model bar of the Hollywood set and imagine Sam and Diane walking in the door and calling your name. You'll find many a tourist in Cheers, but locals tend to stay away to avoid the crowds.

Steeped in history and serving Yankee classics like roast beef rib and Indian pudding since 1828, Durgin-Park is mostly visited by tourists looking to see some old-time Boston character. Happy hour brings in Faneuil Hall 9-to-5ers looking for cheap beer and snacks, like the $3 hot dog and fries.

Crowds of cool Allston students and greater Boston music fans rock hard until closing at Great Scott, which books an impressive lineup of local and visiting indie rock bands (from 9 pm) in live double and triple bills on a varying rotation nearly every night.

This is a subterranean dive with gritty charisma. Live bands hit the stage Thursday to Sunday, including one of the hotspot's most popular events: Sinatra Sundays, where a live Sinatra Band takes the stage at 8 pm. The story goes: when its signboard wasn't ready for the 2001 opening, the owners shrugged, "Ah, so what?" and let the joint go incognito.

This iconic bandbox near Boston University is famed for bringing up big-name talent (think U2), hosting Coldplay, and nurturing local rock and hip-hop acts. Two tiers of booths provide good sight lines from all angles, even some intimate, out-of-the-way corners. Four bars quench the crowd's thirst, and food is available. Some shows are for 18-plus only; many sell out. The newer Paradise Lounge next door is a more intimate space to catch local (often acoustic) songsters, literary readings, poetry slams, and other artsy events.

Since 1989, this intimate and amiable venue overlooking the Charles River has presented top names–-Harry Connick Jr., Chris Botti, Michael Bublé, and Wynton Marsalis, to name a few–-in jazz, Latin, and contemporary, but also blues, soul, R&B, cabaret, and world music. There are full bar and cocktail menus, as well as food and dessert selections. Performances are Thursday through Saturday 8 and 10 pm; tickets range from $25 to $50 and are discounted if you come for dinner. Advance purchase is recommended.

Browse an eccentric collection of books and magazines at this crowded, pleasant café, then have coffee or tea while you read. This is a nice spot for a meal with a date, solo journal writing or reading at the bar, or surfing the net with free Wi-Fi. The windows facing Newbury Street (not to mention the patio) are great for people-watching. Open daily from 8 am until midnight.