The 13 Best Things To Do In Pikeville, Kentucky

Eastern Kentucky has always been an off-the-beaten-path kind of place. The tiny town of Pikeville, with a population of around 7,000, for example, wasn’t accessible to most until the landmark Pikeville Cut-Through Project gave it new life. The initiative built a channel through Peach Orchard Mountain that rerouted the Levisa Fork of the Big Sandy River and allowed for the construction of a four-lane highway connecting Pikeville to other destinations. The project, which began in 1973 and wrapped up 14 years later, not only protected Pikeville’s downtown from frequent flooding, but it helped put the quiet but lively town on the map. “We’re an authentic Eastern Kentucky town that’s really grown by leaps and bounds over the years,” says Jill Dotson, executive director of community relations for the city. Today, you can stroll the charming downtown, enjoy the gorgeous natural mountain surroundings, and learn about two of the country’s most infamous families in Pikeville. Here are the 13 best things to do on a trip to Pikeville, Kentucky.

What To Do In Pikeville, Kentucky

Stroll Down Main Street

If you want to see the best of Pikeville, downtown’s Creative Arts District (located at Main Street and 2nd Street) is the place. With brick pavers, string lights, and a whimsical public arts installation known as Umbrella Alley, this picturesque stretch of road is as charming as it gets. If you’re in the mood for a little retail therapy, stop into The Shoppes at 225, a one-of-a-kind business incubator and indoor market that features seven unique retailers that specialize in everything from apparel to vintage vinyl. For more local love, be sure to attend a Night Market at Pikeville City Park, where artisans sell their wares in a festival-like setting.

pikevillemainstreet.com; 243 Main Street, Pikeville, KY 41501; 606-213-2358

Take A Hatfields And McCoys Tour

There may not be any fiercer or more infamous feud than the one between the Hatfields and McCoys. The 1800s Appalachian families lived around the Kentucky-West Virginia border, and their decades-long feud, involving lying, cheating, stealing, and even murder, is the stuff of legends. Learn all about the two families’ fascinating history on the self-guided Hatfields and McCoys Historic Driving Tour. Pikeville, and surrounding Pike County, is home to many landmarks, sites, and monuments all related to the feud. From gravesites of men and women who lost their lives in the feud to the actual sites where fights and duels took place, there’s plenty to explore. You can find a tour map online, and visit the spots at your own pace.  

tourpikecounty.com

Walk Across The Historic Pauley Bridge

To get a gorgeous glimpse into Pikeville’s past, look no further than the historic Pauley Bridge, a WPA project that began in 1936 and was finished in 1940. The wooden bridge is bookended by imposing sandstone towers on each end that make for a wonderful photo op. With the lush, tree-covered Appalachian mountains all around and the Big Sandy River below, you won’t find a more scenic spot in all of Pikeville. Though the bridge has been closed to cars since 2000, you can still get out and walk the length of the 390-foot-long landmark.

Tour Dueling Barrels Distillery

Located in the heart of downtown, Dueling Barrels is much more than your average distillery. The complex includes a visitor center, tasting room, gift shop, distillery, brewery, and a restaurant called Pearse’s Place. Tours include an entire history of moonshining in Appalachia and Eastern Kentucky, an overview of the distilling process, and four tasting tokens that can be used for beer or moonshine in the brewery and distillery. Live music and karaoke are weekly occurrences, proving that this is one all-encompassing entertainment, drinking, and dining destination.

duelingbarrels.com; 745 Hambley Blvd., Pikeville, KY 41501; 606-766-3835

Explore The Arts At The App

The App, also known as The Appalachian Center for the Arts, is a hub for arts and culture in Pike County. Guests can visit the gallery to see rotating exhibits displaying visual art from local and regional artists. They can also head to the 200-seat theater to see anything from a comedy show to live music and theatre performances.

theapparts.org; 218 Second St., Pikeville, KY 41501; 606-262-4004

See A Show At Appalachian Wireless Arena

Pikeville may be a small town, but the acts who make their way to the Appalachian Wireless Center are anything but. Located in the heart of downtown, the 7,000-seat arena sees hosts artists and performers ranging from The Black Crowes to Soulja Boy to the Harlem Globetrotters. The complex also has an outdoor plaza called the Mountain Top Media Stage that hosts a free music series called Main Street Live during many months of the year.  

appalachianwirelessarena.com; 126 Main Street, Pikeville, KY 41501; 606-444-5500

Take A Hike At Bob Amos Park

With the majestic Appalachian Mountains as a scenic backdrop, outdoor activity is even better at Bob Amos Park. In addition to sport courts, fields, a playground, and walking track, the park is also home to 13 miles of hiking trails, horseback riding opportunities, ziplining, and eight miles of river trails that can be explored via kayak, canoe, or paddle board.

Explore The Grand Canyon Of The South

Located just 30 minutes from downtown Pikeville, Breaks Interstate Park is often referred to as the Grand Canyon of the South due to the fact that it’s home to one of the deepest gorges east of the Mississippi. The Virginia park is a treasure trove of incredible vistas and exciting outdoor adventures. Hike one of 10 beautiful trails, book a tour to see elk living on rehabilitated coal mine sites and forests around the Breaks, get a rush of adrenaline by ziplining the canyon rim, go fishing or kayaking on the Russell Fork River, or spend a day boating on Laurel Lake. For true thrill seekers, you can also white water raft, rock climb, and mountain bike in the park.

breakspark.com; 627 Commission Circle, Breaks, VA 24607; 276-865-4413

Where To Eat In Pikeville, Kentucky

Have A Delicious Italian Meal

You can see a historic site and enjoy a great meal at this restaurant that’s located on the end of Main Street in the former Randolph McCoy House. Chirico’s Ristorante is a multigenerational family-owned business that was started by Frank Ray Chirico back in 1981. Today, the restaurant is run his three sons, who proudly carry on the family tradition and recipes. The menu features all the classics, from brick-oven pizzas and calzones to every type of pasta and fresh bread. For dessert, order a slice of their famous Brickle. The frozen confection is made with fluffy cream cheese, buttery pecan brickle, and creamy caramel atop a graham cracker crust.  

facebook.com/ChiricosRistoranteKY; 235 Main St, Pikeville, KY 41501; 606-432-7070  

Try The Local Barbecue

It’s practically a sin to visit a Southern town without sampling their barbecue. Luckily, Pikeville visitors can get their fix at Biggen’s BBQ. Choose from a jam-packed menu of brisket, ribs, pulled pork, smoked chicken, smoked brats, and more. Don’t forget sides like kale pasta salad, sweet potato casserole, and mac and cheese.

facebook.com/biggensbarbieq; 404 South Mayo Trail, Pikeville, KY 41501

Savor A Steak Dinner

In some ways, Sal’s Steak and Ribs is your classic steakhouse, and in other ways, it’s most definitely not. The family-owned and -operated restaurant is known for serving classic cuts of beef perfectly cooked over a hot flat-top, but it’s also known for its excellent Central American fare, from quesadillas to burritos to fajitas. Start your meal with a plate of Sal’s Rattlers, corn ribs tossed in homemade seasoning and served with lime aioli, and then buckle up for a big meal. You’re guaranteed to leave full and happy no matter which section of the menu you order from.

facebook.com/salssteakandribs; 90 Weddington Branch Road, Pikeville, KY 41501; 606-899-8226

Get An Old-School Smashburger

Known for their smashburgers (many believe the style of burger originated at the restaurant’s nearby Ashland location), Dairy Cheer is a classic roadside joint located just off Route 23. Stop when you see the giant green-and-white sign, and head into the 1970s dining room that’s complete with wood paneling and pastel-colored booths. Serving breakfast, lunch, and dinner—plus plenty of tasty ice cream treats for any time of day—this is the ultimate place to go for a heavy dose of nostalgia. A smashburger, onion rings, and hot fudge sundae or tangerine swirl cone is the perfect order.

facebook.com/DairyCheer; 344 S Mayo Trl, Pikeville, KY 41501; 606-432-5222

Where To Stay In Pikeville, Kentucky

Stay At The Landmark Hotel

Pikeville’s only locally owned accommodation, the Landmark Hotel is a comfortable stay in the heart of town. With four floors of both king and double rooms, there’s plenty of space to house a crowd. An outdoor pool and cozy living room complete with a fireplace make this spot feel like home.

landmarkpikeville.com; 190 S Mayo Trail, Pikeville, KY 41501; 606-432-2545