Get to know the many sides of Asheville with this blog series, which examines Asheville through its unique, colorful, spirited, and incredibly distinct neighborhoods. Next, we’re heading to Hendersonville. 

With the second largest downtown in Western North Carolina, Hendersonville is a city not to be ignored on your next getaway to the area. Just south of Asheville, about 30 minutes down I-26, visitors can explore more than 100 shops and 25 restaurants in the seven-mile stretch of the town. 

In the center city, turn-of-the-twentieth-century brick buildings containing shops, galleries, and restaurants span seven well-manicured blocks around historic Main Street. Pedestrian-friendly and quaint, Hendersonville is a great place to spend a day in WNC. While strolling around town, you might come across a few of the city’s famous painted bears. Every year, the Bearfootin’ Art Walk & Auction lines Main Street with about 20 brightly painted bears created by primarily local artists, raising money for various nonprofits in Hendersonville. 

Hendersonville, also known as Apple County, is the perfect place to find orchards in August-November to explore. Visitors can also stay for the NC Apple Festival, held every year on Labor Day weekend, which kicks off apple season in the region. 

Start your Hendersonville exploration with a quick trip to HenDough Chicken & Donuts for breakfast, which serves artisan donuts, fried chicken, and mouth-watering biscuits. For a more down-home, southern charm experience, visitors should visit Pop’s Diner or Kosta’s Fireside Restaurant & Pancake Inn, two spots that boast some incredible reviews from recent patrons. 

Time to shop! Some of the best places to shop for women’s clothing include Banana Moon and The Sanctuary Boutique. And if you’re looking for a unique store to explore, stop by Homestead Fine Linens, a fine linen and gift emporium. Outdoor enthusiasts should also head to Mast General Store, which has a little bit of something for everyone—especially tourists looking to find the perfect gift to take home. 

For the art-lover, two galleries you can’t miss are Silver Fox Gallery, which has a variety of art and elegant furniture on display, and Woodlands Gallery, a nature-inspired gallery featuring local and regional art, lifestyle, and home products located in Downtown Hendersonville. 

Dive into the area’s history by visiting the Carl Sandburg Home National Historic Site, the late poet’s former homestead, with the bonus of hiking trails and a farm with adorable dairy goats. Last but certainly not least, on your tour, catch a show at Flat Rock Playhouse, the official state theater presenting Broadway-caliber shows. 

When dinner is calling, you must go to Postero, an open kitchen that crafts New American fare; West First Wood-Fired, a wood-fired pizza place; Never Blue, a quirky downtown spot for classy cocktails and tapas; or Elevations Chophouse, a steakhouse that puts a delicious spin on traditional favorites.

Called the “Crest of the Blue Ridge Wine County,” Hendersonville was also titled an American Viticultural Area, a designated wine-grape-growing region in the U.S. that provides an official appellation for the mutual benefit of wineries and consumers, in 2019. Start your wine tour at Burnshirt Vineyards, which offers views of 30 acres of vineyards that can be overlooked from the tasting room. Next, head to Saint Paul Mountain Vineyards, a working vineyard and orchard in Hendersonville that produces wine, hard cider, and spirits. Discover a new favorite varietal at Sawyer Springs Vineyard, a family-run Hendersonville winery that produces small-batch vintages. 

For a taste of the Old World, travel to Stone Ashe Vineyard, a Hendersonville winery focused on replicating Bordeaux, France’s vineyard experience. Move to Marked Tree Vineyard, the first winery in Flat Rock, just outside Hendersonville. And then end your winery tour at Point Lookout Vineyards, a Hendersonville winery that sits atop the southeast slope of Point Lookout Mountain with 30-mile panoramic views. 

If beer is more your speed, Hendersonville also has you covered. A new brewery in the area seems to pop up every few months or so now, with newcomers Oklawaha Brewing and D9 Brewing already making a big name for themselves. Southern Appalachian Brewery specializes in small batches of craft beer and can even be found in most local grocery stores, and Dryfalls Brewery serves beers created by a father-son brewing team. 

Apples, wine country, and bears—oh my! There’s an incredible list of reasons to explore Asheville’s nearby area of Hendersonville. Explore more things to do in Hendersonville on our A Look at Asheville directory.