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Wine barDowntown
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.
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Wine barSouthside
Fifty Fifty Wine and Martini Bar splits its list between serious wine and cold martinis on Station Street in Chattanooga's Southside nightlife strip.
PourA classic gin martini alongside a by-the-glass flight
WineBroad by-the-glass list plus a 50/50 wine club
FoodButter and cheese boards, seasonal shareables
TipOwner Jason Bowers hosts the Chatt Cup bartending competition here; Friday and Saturday it pours until 01:00.
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New AmericanNorth Shore
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.
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SpanishDowntown
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.
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Cocktail barDowntown
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.
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Wine barLookout Mountain
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.