Nightlife in Richmond

Select Local Merchants

In 1783, Captain John Holder established Holder's Tavern along the region's main thoroughfare: the Kentucky River. Now part of Hall's on the River, the site persists some 200-plus years later as a place to gather around food and drinks. Today, visitors dig into classic Southern dishes, ranging from steaks and smoked pork chops to frog legs and a seafood platter stacked with shrimp, oysters, scallops, clams, and fried ocean catfish.

1225 Athens Boonesboro Rd
Winchester,
KY
US

The brick walls of Woody's Sports Bar and Grill showcase large, wall-mounted flat-screen TVs to broadcast multiple sporting events while sheltering burger-bearing wait staff who serve patrons steaming entrees and frosty beverages from the menu. Crackers, crispy celery, and crunchy carrots lounge around a dish of signature beer cheese dip ($3.99) to gossip about the potato skins' designer sour cream purse ($6.75). With the 8-ounce prime rib dinner, choose a cut of tender prime rib and two sides such as a fresh salad or golden fries ($13.95). Slices of roasted turkey, bacon, juicy ham, and tomato cozy up under a rich cream sauce and melted cheese blanket in Woody's hot brown platter ($10.45). The kitchen team exercises one of its most useful assets—patience—to slow cook the pork that bathes in Herschel Walker's #34 barbecue sauce in the pulled-pork barbecue sandwich ($6.25). Meander out to the patio during a pick and jam night, where talented locals tickle eardrums with singing, guitar strumming, and ear-shaped feathers.

923 Bypass Rd
Winchester,
KY
US

Bigg Blue Martini pleases palates with more than 20 specialty martinis, beers from Lexington Brewing Company, and a menu of regional and seasonal favorites served daily until midnight. The extensive list of liquid libations boasts original martinis such as the Old Bigg Blue, made with Kentucky’s Pure Blue vodka, blue island pucker, blue curaçao, and orange juice ($9); and the Bourbon Ball, a sweet blend of Marker’s 46, Godiva dark chocolate, and Frangelico ($9). Start ingestion sessions with Chef Winslow’s four-cheese pimento dip, a creamy blend of smoked gouda, white and sharp cheddar, and parmesan cheeses ($7), before moving onto a state specialty, the Kentucky Hot Brown, a sandwich piled high with turkey, ham, bacon, and tomatoes and blanketed with a creamy cheese sauce ($14). The masterful culinarians rely on fresh, local ingredients to bolster meals, steaming the Bigg Blue mussels in Kentucky Pale Ale ($8), slathering Kentucky-bourbon barbecue sauce on the beef-brisket sandwich ($10), or sprinkling deep-fried bluegrass on everything.

369 W Vine St
Lexington,
KY
US

Yelpers give Natasha’s Bistro & Bar an average of four stars, TripAdvisors give it an average of three owl eyes and 76% of Urbanspooners recommend it.

112 Esplanade Alley
Lexington,
KY
US

Blue Agave Cantina and Tequila Bar serves a menu specializing in marinated meats and margaritas. Guests unable to domesticate their fire hydrant can cool off with a bowl of guacamole, prepared to order from fresh avocados, tomatoes, onions, cilantro, and lime ($6). Entrust hands to tacos, served with salsa, lime, cilantro, and onions on corn tortillas, with your choice of steak, shredded or marinated pork, or chicken ($4 for two). Diners licensed to operate silverware can take a test run with the red-chili and shredded-pork carnitas platter ($11) or the alambres, marinated steak topped with cheese, peppers, and onions, served on a hot skillet ($16).

410 W Short St.
Lexington,
Kentucky
US

Friends Again Grill & Tavern slings classic American pub fare, frosty brews, and entertaining diversions seven days a week. The menu showcases appetizers such as handmade potato skins ($5.99) and fried pickle spears ($5.49) to stir languid taste buds from their slumber as gently as a wake-up call from Enya. Pound down protein with the beer-cheese burger ($7.99), an angus chuck patty topped with beer cheese, or show reverence for poultry with the homemade chicken-salad sandwich ($5.99). Serious sit-down diners can peruse the tavern’s triumphant platters, such as the classic Hot Brown, a slice of bread topped with ham, turkey, cheese, bacon, and a special sauce ($7.99). Friends Again's staff also pours a full bar’s worth of cocktails and brewskis for game night, date night, and discovering your inner Herbert Hoover night.

841 Lane Allen Rd
Lexington,
KY
US