The best bars & nightlife in Annapolis

“Whether you're in the mood to see touring comics or local standups sharpening fresh bits, The Port Comedy Club keeps the laughs rolling with New Material Night, Captain's Quarters, and the delightfully chaotic Walk The Plank panel show. It’s an easy pick for a midweek reset or spontaneous date-night upgrade.”

From the Baltimore newsletter, August 7, 2026

“Power Plant Live! stacks your week with live performances, themed nights, karaoke at Luckie's Tavern, Leinie Lodge & Beer Garden tap takeovers, Geno's Steaks munchies, and giant screens for every game. Rally the crew, make it your fantasy draft HQ, and let a lively mashup of bars and venues handle the fun.”

From the Baltimore newsletter, August 3, 2026

“Tucked inside the Historic Inns of Annapolis, Drummer's Lot Pub keeps it charming and low key, the kind of spot where a simple drink turns into actual relaxation. Ideal when you want easy conversation, a mellow scene, and zero fuss after State Circle shenanigans.”

From the Annapolis newsletter, August 6, 2026

“From the “Original” award-winning Buffalo to Honey Old Bay, Mango Habanero, and Garlic Parm, Kisling's Tavern keeps wing night exciting. Order party platters for the crew or roll solo with a drink, then thank yourself for turning an average week into a saucy victory.”

From the Odenton newsletter, August 5, 2026

“Meander Art Bar is part neighborhood hangout, part creative studio, with hands-on art experiences, rotating classes and community workshops that pair nicely with something from the bar. Rally a friend and make something this week, or plan a private get-together that’s more paint-splattered than small talk.”

From the Columbia newsletter, August 4, 2026

“Big, spicy wings are the draw at this chill American bar & grill with TVs for catching the game.”

“Hip, laid-back watering hole with a sausage-centric menu, a cool microbrew list & craft cocktails.”

“Bohemian haunt bringing together wine by the glass & bottle with eclectic small & large plates.”

“Casual eatery featuring natural wine and creative snacks, plus a patio.”

“Convivial pub featuring classic Gaelic grub & American standards in warm, brick-walled environs.”

“Firehouse-themed pub featuring 40+ draft beers & live music nightly, plus casual seafood & burgers.”

“Relaxed wine bar featuring a global selection of vintages, plus craft cocktails, charcuterie and cheeses.”

“In business since 1975, this cozy bar offers live music nightly, TV sports & dozens of tap brews.”

“Old brick taproom housing Oliver's Breweries, with British-style ales, creative pub fare & events.”

“Restaurant featuring casual fare, as well as a wine store and tasting room.”

“Brick-walled tavern with a wisteria-covered heated patio serving pub fare & regional seafood dishes.”

“Refined gin-focused bar whipping up creative cocktails, plus tapas, sharing plates & sandwiches.”

“Signature cocktails, craft beer & small plates prepped in a dimly lit setting with white-tile walls.”

“Intimate nook with 1920s flair offering bourbon & beer, plus refined takes on American comfort food.”

“Roomy venue in the Power Plant with nationally headlining comedians & pub grub some nights.”

“Long-running (since the 1920s) neighborhood joint known for its crab cakes & creative pub fare.”

“A farm-to-table New American menu is paired with a deep wine list in this cottagelike restaurant.”