Nightlife in Winchester

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.

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.

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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.

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).

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.