Portland

Maine, USA

Old Port cobbles, Congress arts, Munjoy views

City score

GAME
Daygame
Nightgame
Online
WOMEN
Hot
Receptive
Volume
CITY
City
Crime

Daygame

  1. 0
    Exchange Street
    Old Port shops, cobbles toward Congress
  2. 0
    Congress Street
    Arts District bookstores, First Friday walk
  3. 0
    Eastern Promenade
    Munjoy lawn, Casco Bay, till 10

Nightgame

  1. 0
    Bubba's Sulky Lounge FriSat
    Light-up floors, 80s Friday, antiques
  2. 0
    Flask Lounge ThuFriSat
    West End DJs, karaoke Thursdays
  3. 0
    Oasis FriSat
    Wharf Street line, upstairs dance floor

Date ideas

  1. 0
    Grace
    Bar, quiet enough to talk, Chestnut Street Bar
  2. 0
    Gritty McDuff's
    Pub, quiet enough to talk, Fore Street Bar
  3. 0
    Moonday Coffee
    Coffee, Washington Ave Coffee
  4. 0
    The Gelato Fiasco
    Ice cream, take it and walk, Fore Street Grab-and-go
  5. 0
    Another Round
    Board games, coffee, talk lands itself Boardgame café
  6. 0
    Portland Museum of Art
    Art museum, Congress Sq Museum
  7. 0
    Clark Manor
    Manor house, Western Promenade Estate

Second date

  1. 0
    Luna Rooftop Bar
    Canopy roof, harbor cranes, walk-in
  2. 0
    Top of the East
    15th-floor glass lounge, city-wide view
  3. 0
    Portland Museum of Art
    Congress Square, Friday till 8
  4. 0
    Bayside Bowl
    Lanes plus 2026 rooftop concerts
  5. 0
    Casco Bay Lines
    Peaks ferry, 365-day Casco run

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