Food & Drink 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.

Connected by an asphalt web of highways, state roads, and thoroughfares, blocky yellow signs gleam nonstop, casting a dandelion glow from the words “Waffle House.” The booths at the eateries fill 24 hours each day with the aromas of sizzling pork chops, Jimmy Dean sausage, and endless mugs of coffee. Line cooks brown shredded potatoes on a grill as waiters shout back in a language all their own for hash browns “smothered,” “covered,” or “topped”—served with onions, cheese, or chili, respectively. Angus burgers and steak melts share space on the rippling-hot surface at all times of day, allowing tired drivers to stop for food when they are on a long journey or just listening to an 11-hour drum solo on the radio. The first Waffle House switched on its lights in 1955, and some menu items still bear the names of Waffle House staff of the past, including Bert's chili from Dallas and Alice's iced tea.

In 1921, Ruth Hunt turned a penchant for candy-making into a business that quickly outgrew her home’s kitchen. Today, guests can visit the factory in Mt. Sterling and peruse a selection of more than 70 candy varieties and gifts such as signature boxes, gift baskets, holiday tins filled with the companies' favorite products, Elmwood Inn teas, Ale 8 One products, Kentucky cookbooks, and simply Kentucky jam cakes. Ruth Hunt Candies is a KY Proud company where customers during factory tours can see chefs stilling using original methods, making candy by hand as well as using the same copper kettles that Ruth Tharpe Hunt used to mix together high quality ingredients including real whipping cream, roasted nuts, and additive-free chocolate.

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.

Jerry's Restaurant opened in 1961, and since then it's served family-style meals, which incorporate some of the 15+ vegetables the kitchen uses. The team cooks breakfast, lunch, dinner, and whatever meal humans think up next. Their food ranges from cheesy spaghetti and lemon-pepper chicken entrees to potato skin and onion ring entrees. Jerry's serves the popular J-Boy sandwich—a double-decker cheeseburger with a special sauce—and even a hot fudge cake.

While there aren't many online reviews for Smashburger's newly opened Nicholasville Rd. location, six Yelpers give the Upper Street location a 3.5-star average: