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 Elliot Marsh, 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.
Guided tour · 3 hours
Discover the flavors of Chattanooga on a food tour of the Southside neighborhood. Learn about the history of the area and the food from a trained guide.
Guided tour · 3 hours
Discover the flavors of Chattanooga on a guided food tour of the downtown district. Savor the flavors of the city as you enjoy a variety of dishes at up to four curate...
Guided tour · 3 hours
Discover the flavors of Chattanooga on a food-focused walking tour. Visit four different restaurants and meet the proprietors behind them, all while tasting tapas-size...
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.
PourHalf-price bottles every Tuesday night
WineUnusual, natural-leaning bottles
FoodAppalachian-inspired kitchen to 22:00
Tip21 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.
PourCava at sunset on the terrace
WineSpanish bottles, sherry and cava
FoodTapas and conservas
TipClosed 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.
PourAn astrology-inspired house cocktail under the star ceiling
WineShort, sharp list beside a cocktail-first bar
FoodBar snacks
TipRevived 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.
PourA glass on the tree-canopy patio at sundown
WineApproachable by-the-glass list with tasting nights
FoodPastries and light boards
TipClosed 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.
PourWhatever McCune is opening for the counter that night
Wine75+ wines by the glass, old and new world
FoodCharcuterie boards
TipLive music Saturdays and open-mic nights midweek; closed Sunday and Monday, and seats are few, so arrive at 17:00 open.
