The best bars & nightlife in Richmond

“Small-batch, curiosity-fueled pours and experimental runs make Ghost Fox Winery a fun detour just up the road in Nicholasville. The tasting room opened in 2023 and keeps things no frills, all flavor, with easy reservations and private parties if you're corralling a crew.”

From the Richmond newsletter, September 2, 2026

“The Home Stretch Bar and Grill keeps it simple in the best way, with lunch and dinner, a full bar and wine selection, a full menu, plus daily specials that hit when you’re over cooking. Easygoing vibe, solid plates, and a place you’ll actually see your neighbors.”

From the Richmond newsletter, September 10, 2026

“Craving something local and legendary? Madison Garden Bar and Grill has been making memories since 1982 with Buff Stuff dry-rub wings, Angus burgers, and pizza, plus the area’s largest craft beer and bourbon selection and live events that turn a quick bite into a night.”

From the Richmond newsletter, September 3, 2026

“m. hunger hits, Wink's Bar is the kind of down-home spot where a juicy burger or oozy grilled cheese pairs with an easy cocktail or cold beer. Zero pretense, just solid comfort food and a relaxed vibe that feels perfectly Richmond.”

From the Richmond newsletter, August 29, 2026

“When your week calls for an easy win, Blue Stallion Brewing Company Richmond Taproom / Holler Burger pairs crisp, German-style beers with smash burgers and fresh-cut fries.”

From the Richmond newsletter, September 22, 2026

“Burgers & Irish classics are served in a homey dark-wood pub that features regular live music.”

“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.”

From the Richmond newsletter, September 15, 2026

“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.”

From the Richmond newsletter, September 18, 2026

“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.”

From the Lexington newsletter, September 12, 2026