Night 🌙

Pubs & Pints

• Drummer's Lot – Historic tavern dating back to 1784; George Washington and Thomas Jefferson were rumored visitors. (16 Church Circle, 5 pm–12 am​​
• Ram's Head Tavern, Downstairs Pub – Quaint 1830s pub with ghost stories and local charm. (33 West St, 11 am–10 pm)
• 1747 Pub – Beneath Reynolds Tavern, enjoy drinks and summer Shakespeare performances. (7 Church Circle, 11 am–11 pm)

Irish Pubs

• Galway Bay – Classic Irish pub fare, whisky, and Guinness. (63 Maryland Ave, 11 am–12 am)
• McGarvey's – Irish bar with a U.S. Naval Academy twist. (8 Market Space, 11:30 am–1:30 am)

Music & Downtown Nightlife

• Middleton's Tavern – Upstairs piano bar, weekend vibes until 1 am; downstairs open til 12 am. (2 Market Space)
• The Choptank Annapolis – Waterfront rooftop for Maryland’s famous “Crush” cocktail and live weekend music. (110 Compromise St, 11 am – 2 am)
• O'Brien's Oyster Bar & Seafood Tavern – Every Friday and Saturday, dance the night away with one of our live DJs, on Downtown Annapolis' largest dance floor! (113 Main Street, 10 pm - 1:45 am)
• Ponche Tiki Bar – Located upstairs inside of Pearl Restaurant, this hotspot blends artisan cocktails & gourmet fare. Chic ambiance, locally sourced ingredients, expertly crafted drinks. (26 Market Space, 5 pm - 12/2 am)

Dessert Stops

• Annapolis Ice Cream Company – Homemade, inventive flavors. (96 Main St, 2 pm–9 pm)
• Kilwins Annapolis – Chocolates, fudge, and ice cream. (128 Main St, 10 am–10 pm)
• Red Bean – Coffee and affogato heaven. (220 Main St, 9 am–10 pm)

Off the Beaten Path

• Parley Room – Sip small-batch gin or vodka inside one of the city’s oldest buildings. (25 State Circle, 4 pm–10 pm)
• Harold Black – Speakeasy vibes, curated cocktails, and late-night Italian bites. (26 Main St, 5 pm–12 am)
• The Choptank Annapolis – Waterfront views, live music, and rooftop sunsets. (8 Compromise St, 11 am–12 am)
• Metropolitan Kitchen & Lounge – Arts District rooftop bar for happy hour, cocktails, and selfies. (15 West St, 4 pm–1:30 am)
• Fox's Den – Great selection of American Beer and Spirits along with incredible comfort food anchored by wood-fired brick oven pizzas.(179B Main Street, 5 pm - 9/10pm)