Tapster lets you build your night your way with a self-pour tap wall of rotating beer, wine, cocktails and yes, bourbon. Start with a quick…
401 W Main St #101 (Lexington) · ✓ checked Jul 31
“Tapster lets you build your night your way with a self-pour tap wall of rotating beer, wine, cocktails and yes, bourbon. Start with a quick splash or settle in with a favorite, maybe hit a trivia night this week and call it a win.”
Darling Wine Bar keeps wine fun and un-snobby, with a rotating glass list that always spans reds, whites, bubbles, rosé, and orange, plus a…
101 W Loudon Ave (Lexington) · ✓ checked Jul 31
“Darling Wine Bar keeps wine fun and un-snobby, with a rotating glass list that always spans reds, whites, bubbles, rosé, and orange, plus a bottle shop and seasonal cocktails where spritzes never clock out.”
OBC Kitchen is the rare Lexington mashup of chef-driven Southern plates and an almost-museum-level bourbon collection, backed by thoughtful…
3373 Tates Creek Rd (Lexington)
“OBC Kitchen is the rare Lexington mashup of chef-driven Southern plates and an almost-museum-level bourbon collection, backed by thoughtful craft beers and wines. Settle in for crispy, soulful bites, pick a pour from the vault, then congratulate yourself on excellent life choices.”
Whether you’re team dry, funky, or crisp, Wise Bird Cider Co. is pouring small‑batch cider made from Kentucky apples and cider‑specific…
1170 Manchester St #140 (Lexington) · ✓ checked Sep 12
“Whether you’re team dry, funky, or crisp, Wise Bird Cider Co. is pouring small‑batch cider made from Kentucky apples and cider‑specific varieties from Virginia, Ohio, and Pennsylvania, with Little Fork slinging a smash burger, shareable boards, and seasonal bites like a Chistorra Sausage Skewer and twice‑fried tofu.”
Skip the same-old bar routine and hit Trifecta Cocktail Lounge, where you can watch molten glass become art while sipping creative pours…
243 Walton Ave (Lexington)
“Skip the same-old bar routine and hit Trifecta Cocktail Lounge, where you can watch molten glass become art while sipping creative pours like the locally tipped Mary Todd Sour. Book a glassblowing class or just hang in the gallery lounge and let the sparks boost your week.”
Belle's Cocktail House shakes up playful, polished drinks like Naked in the Garden and Purple Rain, plus dessert-y trouble like Gimme…
156 Market St (Lexington)
“Belle's Cocktail House shakes up playful, polished drinks like Naked in the Garden and Purple Rain, plus dessert-y trouble like Gimme S’more, so your weeknight catch-ups suddenly feel like occasions. Try the Aloha Bitches or Matcha Magic if you like fruity sparkle or a little green tea glow.”
Bourbon on Rye is the low-key spot for pub grub classics and shareable bites paired with a dedicated bourbon list, plus craft cocktails,…
115 W Main St (Lexington)
“Bourbon on Rye is the low-key spot for pub grub classics and shareable bites paired with a dedicated bourbon list, plus craft cocktails, beer and wine. Ideal when you want a relaxed hang, a solid pour, and food that hits the spot without trying too hard.”
East End Tap and Table keeps weeknights easy with a craft beer lineup, proper cocktails, and an Asian-American fusion menu that actually…
333 E Main St Unit 180 (Lexington) · ✓ checked Sep 1
“East End Tap and Table keeps weeknights easy with a craft beer lineup, proper cocktails, and an Asian-American fusion menu that actually delivers. It’s the kind of roomy, laid-back spot where your crew can hang, share plates, and debate whether spicy or sweet wins tonight.”
Georgie's Social House pours original cocktails dreamed up by mixologist Donny and named for famous Georges, plus zero-proof options,…
161 N Limestone (Lexington)
“Georgie's Social House pours original cocktails dreamed up by mixologist Donny and named for famous Georges, plus zero-proof options, chef-prepped charcuterie and hotdogs, and a serious wine and bourbon lineup. This week, try The Force espresso martini made with Lussi Brown cold brew.”
Centro keeps downtown nights easy with no-fuss craft cocktails, local drafts, and a deep bourbon lineup with flights to explore. The…
113 Cheapside Park (Lexington)
“Centro keeps downtown nights easy with no-fuss craft cocktails, local drafts, and a deep bourbon lineup with flights to explore. The brick-lined room and patio that opens to the street make it perfect for post-Rupp hangs, Farmers Market sips, or just catching up with friendly bartenders and neighbors.”
All-day brunch, crispy thin-crust pizza, hand-breaded tenders, and rotating craft taps make Cocktails Too an easy yes whenever the craving…
130 W Tiverton Way #195 (Lexington) · ✓ checked Aug 7
“All-day brunch, crispy thin-crust pizza, hand-breaded tenders, and rotating craft taps make Cocktails Too an easy yes whenever the craving hits. Add karaoke nights and live music on weekends, and you’ve got your go-to for laid-back eats, cold beers, and low-stress fun.”
From the Nicholasville newsletter, September 13, 2026
Comedy Off Broadway is an intimate, adults-only club that brings well-known acts to a tight room where the laughs hit harder, plus a…
161 Lexington Green Cir Unit C4 (Lexington)
“Comedy Off Broadway is an intimate, adults-only club that brings well-known acts to a tight room where the laughs hit harder, plus a low-stakes one-drink minimum whether booze or soda. Keep an eye on their rotating calendar with open mics and touring headliners if you need a weeknight reset.”
Gillum's Sports Lounge nails the local hang vibe with crispy wings, stacked burgers, legit pizzas, and Big Randall Breadsticks that…
830 Eastern Bypass (Richmond)
“Gillum's Sports Lounge nails the local hang vibe with crispy wings, stacked burgers, legit pizzas, and Big Randall Breadsticks that disappear way too fast, plus a full-service bar for a cold one while you catch the game. Low-key, reliable, and exactly what this week needs.”
Chenault Vineyards is Richmond’s easy win this week, with on-site handcrafted wines, a tasting room menu that actually hits, and live…
2284 Barnes Mill Rd (Richmond)
“Chenault Vineyards is Richmond’s easy win this week, with on-site handcrafted wines, a tasting room menu that actually hits, and live music, trivia nights, and themed dinners on the calendar. Grab a tasting, wander the scenic trails, maybe sneak a tour, then linger for dinner and the views.”
Proud Mary BBQ is your indoor/outdoor go-to for legit barbecue, crispy fried catfish, and even frog legs, paired with cold drinks and live…
9079 Old Richmond Rd (Lexington)
“Proud Mary BBQ is your indoor/outdoor go-to for legit barbecue, crispy fried catfish, and even frog legs, paired with cold drinks and live local music that hits just right. Midweek slump or weekend win, treat yourself to a laid-back Bluegrass soundtrack and plates that taste like summer.”
