5 Best Bars in Harvard Square, Boston

Joan Baez, Bob Dylan, Josh Ritter, Lake Street Dive—thousands of folkies have strummed and warbled their way through Club Passim, one of America's oldest (1958) and most renowned clubs for Americana and roots music. Audience participation is encouraged, so be ready to sing along. The ultracozy brick basement has a kitchen that's open for relaxed live-music dining (which is only available to ticket holders). If you travel with your guitar, call about open-mic nights. Classes and workshops at their school around the corner carry on folk traditions. Acoustic bands perform nightly; expect to pay a $5–$35 cover.

This quintessential grad-student hangout is cavelike, low-lit, and brick-walled. During early evenings, tasty entrées like buffalo chicken dip, burritos, brisket nachos, and burgers are half price with a $4-per-person drink (inside only; not on outdoor patio). Named after Grendel, the antagonist in the Old English poem Beowulf, there's nothing but neighborhood love here as you raise a pint in this half-century-old hangout.

Located inside Cambridge's Charles Hotel, Regattabar is the go-to spot for jazz and world music in Cambridge, featuring regulars including leading legends (Ron Carter, Joe Lovano, Lee Konitz), top guitarists (John Scofield, Mike Stern, Pat Martino), and local favorites. It was even listed in Rolling Stone magazine as one of the best jazz bars in the nation. Tickets for shows run about $25–$65. The dimly lit 220-seat club with subtle nautical decor offers tasty fare and drinks.

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.

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.