Annapolis

Maryland, USA

West Street drinks, Main Street pubs, Eastport over the bridge

City score

GAME
Daygame
Nightgame
Online
WOMEN
Hot
Receptive
Volume
CITY
City
Crime

Daygame

  1. 0
    Main Street
    Shops downhill to the water, dock end fenced
  2. 0
    West Street Arts District
    Galleries and patios, First Sunday festival flow
  3. 0
    Maryland Avenue
    Brick antique row, State Circle to the Academy
  4. 0
    Annapolis Town Center
    Parole open-air mall, weekend retail loops

Nightgame

  1. 0
    O'Brien's Oyster Bar & Seafood Tavern FriSat
    Downtown's biggest dance floor, DJs till 1:45
  2. 0
    Rams Head Tavern ThuFriSat
    Wisteria patio, Fordham pints, locals' second home
  3. 0
    Middleton Tavern FriSat
    1750 room on Market Space, oyster shooters
  4. 0
    Metropolitan FriSat
    Upper West Street, live music, late upstairs

Date ideas

  1. 0
    Dry 85
    Bar, quiet enough to talk, Main Street Bar
  2. 0
    Red Red Wine Bar
    Bar, quiet enough to talk, Main Street Bar
  3. 0
    Bean Rush cafe
    Coffee, quiet enough to talk, Annapolis Street Coffee
  4. 0
    Annapolis Ice Cream Company
    Ice cream, take it and walk, Main Street Grab-and-go
  5. 0
    Naval Academy Museum
    Museum Museum
  6. 0
    McKeldin Planetarium
    Planetarium Planetarium

Second date

  1. 0
    Schooner Woodwind
    Seventy-four-foot schooner, sunset sail, help hoist
  2. 0
    Rams Head On Stage
    Seated West Street club, touring acts, dinner
  3. 0
    William Paca House & Garden
    Georgian rooms, two-acre terraced pleasure garden
  4. 0
    Annapolis Maritime Museum
    Old oyster house on Back Creek, daytime only
  5. 0
    Carrol's Creek Cafe
    Eastport waterfront, skyline back across Spa Creek
  6. 0
    United States Naval Academy Yard
    Guided Yard tour, walk in Gate One, REAL ID

Last updated 2026-09-15. Venues change. Check before you go, and vote so the list stays honest.