6 Best Bars in Boston, Massachusetts

America's oldest continuously operating pub (founded 1795) is named after its original owner, town crier Jimmy Wilson, whose bell-ringing wooden sign still hangs on the wall. On the edge of the Freedom Trail, this glassed-in flatiron pub serves fried haddock sandwiches, burgers, and New England's favorite entrées, against a background of live music. Bands (and the occasional comedian) play each night downstairs, and DJs spin Top 40 for dancers Thursday through Saturday upstairs; there's karaoke every Tuesday. Expect long lines of twentysomethings on the weekends.

Hung with 20 bright county banners, decorated with pictures of Ireland and portraits of Samuel Beckett, Lady Gregory, and James Joyce, The Rose draws as many tourists as Ireland-loving locals. Friendly Irish bartenders serve up pints, blarney, and far more Irish whiskeys (28) than Scotches (12). Nightly shows by traditional Irish and contemporary musicians confirm its abiding Gaelic good cheer, or craic. Dine on Guinness beef stew and fish-and-chips—all served by staffers with authentic brogues.

Open-windowed, multiroomed Clerys can be your neighborhood bar, Irish pub, dance hall, sports hub, trivia game spot, or even the home for local Georgia Bulldogs sports fans. Expect long lines on weekend nights when DJs take the state from 10 pm to close; its several rooms bustle with young professionals. Food ranges from bar snacks such as nachos, wings, pizza, and burgers, to main events like steak tips and vodka pasta.

British expats and other football (not the American kind) fanatics head to this Downtown pub to watch English Premier League, MLS, and LaLiga matches live—which means opening time can be early. We think it's a great excuse for 7 am pint of Fuller's. The menu features pub grub with British flair, from burgers to butter chicken to a flight of four savory potpies. Check out the happy hour snack specials Monday through Friday 3–6 pm.

Less rowdy than its Faneuil Hall neighbors, this now-Irish bar claims to have housed the "Headquarters of the Revolution" and was the inn where silversmith Paul Revere overheard plans for a British assault on Lexington and Concord, prompting his famous ride. While yesteryear found John Hancock (whose brother lived next door) strolling past its doors, today The Green Dragon is known for a great Guinness pour and Irish music—soloists play in the evenings from 5 to 9 Wednesday through Friday, and bands bring it on most weekend nights beginning at 9. There's comedy night every Monday and a selection of Top 40 cover bands playing Tuesday through Sunday. College kids and young professionals tend to crowd the bar in the evenings.

Grab a seat by the windows overlooking Faneuil Hall on hot summer days, or cozy up to a coal fireplace in winter, and enjoy your pint (or a pick from one of the largest selections of single malt whiskies in Boston). There's live music at Hennessy's most nights of the week, as well as plenty of rowdy crowds that overrun the yellow-and-black confines for Top 40 cover bands mixed with DJs on weekends from 9 pm to 1 am at Upstairs at Hennessy's.