Fifty Fifty Wine and Martini Bar splits its list between serious wine and cold martinis on Station Street in Chattanooga's Southside nightlife strip.
Editorially verified August 18, 2026 by Lewis Vaughan, TableJourney editor. Source.
Food program: Butter and cheese boards, seasonal shareables
Tip: Owner Jason Bowers hosts the Chatt Cup bartending competition here; Friday and Saturday it pours until 01:00.
Address: 43 Station Street, Chattanooga, TN 37408
The Rosecomb built its bar around unusual wines and the best beers it can find, poured in a 1920s cottage garden in Chattanooga's Riverview blocks.
Signature pour: Half-price bottles every Tuesday night
Wine focus: Unusual, natural-leaning bottles
Food: Appalachian-inspired kitchen to 22:00
Tip: 21 and over only. Kitchen closes at 22:00 while the bar runs later; Sunday is a daytime 11:00 to 16:00 service.
Paloma Bar de Tapas matches Spanish wines and sherry with tapas on the Westin Chattanooga's tenth-floor rooftop on Pine Street, sunset views included.
Signature pour: Cava at sunset on the terrace
Wine focus: Spanish bottles, sherry and cava
Food: Tapas and conservas
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 mixes tarot-themed cocktails and keeps a tight wine list under an artificial night sky at the Dwell Hotel in downtown Chattanooga.
Signature pour: An astrology-inspired house cocktail under the star ceiling
Wine focus: Short, sharp list beside a cocktail-first bar
Food: Bar snacks
Tip: Revived at the start of 2026 after a pause; nightly 16:00 to midnight, and the velvet front room suits small groups.
Canopy Coffee and Wine Bar pivots from morning espresso to evening pours on Scenic Highway up Lookout Mountain, just outside Chattanooga proper.
Signature pour: A glass on the tree-canopy patio at sundown
Wine focus: Approachable by-the-glass list with tasting nights
Food: Pastries and light boards
Tip: Closed Sunday. It doubles as the mountain's coffee shop from 07:00, so evening wine crowds are calmest midweek.
JMac's Vino & Vinyl pours more than 75 wines by the glass to vintage records on Georgia Avenue in downtown Chattanooga, sommelier John McCune's room.
Signature pour: Whatever McCune is opening for the counter that night
Wine focus: 75+ wines by the glass, old and new world
Food: Charcuterie boards
Tip: Live music Saturdays and open-mic nights midweek; closed Sunday and Monday, and seats are few, so arrive at 17:00 open.
