The best bars & nightlife in Anne Arundel County

“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, September 16, 2026

“Red Red Wine Bar + Bistro nails the Maryland-coastal-meets-California-fusion thing with stone-fired pizzas, fresh local seafood and straight-from-the-grill goodness, all from a made-from-scratch, ingredient-driven kitchen. Cozy, Bohemian vibes with a nod to New Orleans make it a perfect spot to sip and stay awhile.”

From the Annapolis newsletter, September 30, 2026

“Galway Bay Irish Restaurant and Pub nails the classics with hearty Gaelic fare, pub comforts, and a Guinness Perfect Pint Champion pour. Locals know to catch trad music sessions, a rousing Pub Quiz, and when the season hits, the Galway Bay Eggnog and Egg Nog Cocktail Menu.”

From the Annapolis newsletter, October 7, 2026

“Casual, sports-centric bar and grill with burgers, wings, and tacos, plus karaoke.”

“Relaxed bar serving cocktails and pizza as well as wings and other pub eats.”

“Relaxed bar offering beer, wine, and cocktails, plus pool and live performances.”

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

“Rams Head Tavern is the kind of historic hangout locals claim as a second home, with modern tavern fare, an extensive beverage list, and that wisteria-covered patio calling your name. Bonus points for free weekly live music and Rams Head On Stage bringing 300+ concerts a year.”

From the Annapolis newsletter, October 14, 2026

“DRY 85 nails the 1920s vibe with a bourbon and beer lineup, then elevates comfort food into something you actually want to linger over. When the week gets loud, slip in for something smooth, something hearty, and a reminder that Annapolis still does cozy right.”

From the Annapolis newsletter, September 25, 2026

“With roots back to the 1920s and an everyone-knows-your-name vibe, Davis' Pub is the kind of spot that quietly improves your week. Go for traditional Maryland-style lump crab cakes, the crab pretzel piled with Back Creek crab dip, and other comfort-forward pub plates that pair perfectly with weeknight catch-ups.”

From the Annapolis newsletter, September 22, 2026

“Vin 909 Winecafe' keeps things local with farm fresh, organic ingredients on an ever changing seasonal menu, plus hand formed brick oven pizzas using an original family dough recipe that’s unlike anything else in Annapolis. Pair with 40+ carefully selected New and Old World wines by the glass, or a small batch beer.”

From the Annapolis newsletter, October 11, 2026