Whiskey Thief ★ 4.5
Cocktail bar$$$downtownMon-Thu 16:00-23:00; Fri 16:00-24:00; Sat 14:00-24:00; Sun 14:00-21:00
Whiskey Thief was Chattanooga's first rooftop cocktail lounge and remains its best, 100 whiskeys poured above the Edwin Hotel and the river bridges.
Tip: The roof opens at 14:00 on Saturday and Sunday and at 16:00 the rest of the week; Sunday is the early close, at 21:00.
Paloma Bar de Tapas ★ 4.4
Spanish$$$downtownMon-Thu 16:00-23:00; Fri-Sat 16:00-24:00; closed Sunday
Paloma Bar de Tapas holds down the Westin's tenth floor with Spanish wines, gin tonicas and late tapas over downtown Chattanooga's rooftop skyline.
Tip: Closed Sunday; happy hour runs 16:00 to 19:00 on weekdays and the terrace rail tables go first in fair weather.
Matilda Midnight ★ 4.3
Cocktail bar$$downtownDaily 16:00-24:00
Matilda Midnight hides behind the Dwell Hotel lobby in downtown Chattanooga, a jewel-box bar mixing tarot-themed cocktails under a false night sky.
Tip: Revived at the start of 2026 after a pause; nightly 16:00 to midnight, and the velvet front room suits small groups.
Alan Gold's Discotheque ★ 3.9
Cocktail bar$mccallieThu-Sat 20:00-02:45
Alan Gold's Discotheque has been Chattanooga's LGBTQ+ anchor on McCallie Avenue since the 1980s, drag shows, dancing and a crowd that spans the decades.
Tip: Thursday to Saturday only, 20:00 to 02:45; drag showtimes post on the club's events page, and the floor peaks after midnight.
JMac's Vino & Vinyl ★ 4.5
Wine bar$$downtownTue-Wed 17:00-22:00; Thu-Sat 17:00-23:00; closed Sun-Mon
JMac's Vino & Vinyl is Chattanooga's wine-and-records listening room on Georgia Avenue, sommelier John McCune pairing pours with whatever spins next.
Tip: Live music Saturdays and open-mic nights midweek; closed Sunday and Monday, and seats are few, so arrive at 17:00 open.
Pickle Barrel ★ 4.2
American$$downtownMon 18:00-03:00; Tue-Sat 11:00-03:00; Sun 12:00-03:00
Pickle Barrel is the Chattanooga dive of record, a flatiron wedge on Market Street pouring until 03:00 nightly with a roof deck over the downtown grid.
Tip: Strictly 21 and over at all times. The wedge-shaped roof deck is the best people-watching perch downtown.