Gritty McDuff's is Maine's original microbrewery and a Portland institution. It opened in 1988, but with its copper-topped brick bar and wood-beam ceiling, you'd think it had been around at least a century. Gritty's Best Brown, Black Fly Stout, and six other home brews are mainlined from the tanks in the basement. Live bands play on the weekends—mostly original bluegrass or rock 'n' roll covers—and draw a boisterous crowd of locals and out-of-towners. For a little breathing room, head downstairs, past the brewing quarters, to the basement bar and its barrel tables for a more intimate communion with your handcrafted ale.

Open daily 11:30 am to 1 am.

Want to drink like a sailor? Look no further than this perennial favorite where lobstering and fish-hauling captains—along with a few local landlubbers—come to slurp fresh oysters and down pints of Allagash and dirty martinis. From the outside, the harborside shack isn't much to look at, but the shiplike interior is all polished mahogany, antique nautical maps, and a beautiful brass bar. Tourists sometimes get the ugly eye when they step through the door, but after your fifth drink, a round of oysters, and a few rambling tales of the open water from the surly lobsterman seated beside you, you'll feel as if you're part of the crew. Arrive early if you want a seat on the patio.

Open Mondays through Saturdays 11:30 am to 1 am, Sundays noon to midnight.