JONESBOROUGH LOOKS LIKE an antique postcard. Walk down Main Street, and you’ll see a red brick courthouse to the right, a church steeple behind it, and a general store at the corner. The uneven sidewalks of the historic district are lined with old buildings that house cafés, antique shops, and clothing boutiques where the wooden floors creak beneath your feet. But then you pass the new, 14,000-square-foot International Storytelling Center, which hosts hundreds of professional storytellers each year for the National Storytelling Festival. A couple holding cups of Dunkin’ Donuts coffee walks by, pushing a double stroller, and you’re back in the present day.
Jonesborough, founded in 1779, is the oldest town in Tennessee, about eight miles west of Johnson City at the base of the Great Smoky Mountains. Home to about 6,000 residents, it’s a hub for kid-friendly activities and festivals and just a three-hour drive from Charlotte, so I take my six-year-old for the last weekend of his summer vacation.
Its heritage is a source of pride, and local storeowners will tell you about it if you ask. But the tour guides dressed in period clothing won’t blitz you with names of battles and war heroes. An hour-long walking tour is a leisurely stroll through the historic district. Our guide, Joel, tells a few stories of Daniel Boone and Andrew Jackson, eastern Tennessee’s early pioneers, but it’s the ongoing construction of the East Tennessee Railway—and the sight of a real-life train chugging down the tracks!—that holds my son’s attention.
Jonesborough, with an area of only four square miles, is that kind of wholesome; think of it as a smaller, less kitschy version of Colonial Williamsburg. Johnson City, a blossoming, live music-rich town of nearly 70,000 with breweries and nightlife, is a 20-minute drive to the east. But Jonesborough is the kind of place where you can ditch your car and let your kids lead the way down a main drag that’s less than a mile long—and with a history lesson, or a story, at every turn.
We check into our room at the Historic Eureka Inn, a bed-and-breakfast run by Jonesborough residents Blake and Katelyn Yarbrough. The two-story hotel, Blake explains, is one of the only original wood structures that survived fires in the late 1890s. The restored inn has 13 guest rooms with Victorian-era furniture and antiques, but also WiFi and central air-conditioning. After we investigate the common areas and sit in every. single. one. of the 12 rocking chairs on the upstairs porch (because he’s six), we head down the street for lunch at the Main Street Café.
The breakfast and lunch spot, opened 37 years ago by locals Herman and Beverly Jenkins, is packed on Saturdays. Today it’s run by their son Zac and his wife Kati, but Beverly’s artwork still hangs on the walls. When it’s our turn at the counter, the woman behind us tells me the chicken salad is divine, so I go with her recommendation (accurate) and try to distract my child from the dessert case brimming with homemade cakes, pies, and cookies. He’d already spotted The Lollipop Shop down the street, and I promised him that would be our next stop.
Like any kid with a pulse, he beelines it to the candy store’s canary yellow awnings and hops into the pint-sized vintage cars underneath. Inside, we find wall-to-wall bins of candy, retro toys, and bottled sodas in flavors like peanut butter, pumpkin pie, and sweet corn. We fill a bag with lollipops and taffy and head to the Chuckey Depot Museum to play in the 48-year-old caboose outside. For the rest of the afternoon, we peruse handmade jewelry and paper crafts at the Makers Faire at Mill Spring Park.
After dinner at Texas Burritos & More, we walk back toward The Lollipop Shop for Movies on Main, which the town hosts on Saturday nights in the summer. Tonight’s flick is The Secret Life of Pets 2, and by 8 p.m., this section of Main Street is blocked off so families can set up lawn chairs and watch the movie on a big screen in the street. Before the show, Lollipop Shop owner Jeff Gurley hosts a rousing game of candy bingo, which goes on for nearly an hour. Tonight, he won’t say no to requests for just one more round. It’s the last weekend of summer, and these kids aren’t ready for it to end.
When the movie’s done, we fold up our chairs and walk back to the inn. I smile and whisper goodnight to the couple from earlier—the one with the Dunkin’ Donuts coffee—carrying their little ones, already asleep.
At the Made Around Here Market (Nov. 8-10), find hundreds of gifts and holiday décor from local vendors at the Jonesborough Visitors Center. Admission is free, but donations benefit the town’s December children’s event, Fun with Frosty and Friends.
ENJOY HOLIDAY CHEER
Christmas in Olde Jonesborough events start in late November. Visit Santa, browse the Christmas Market, and see the lighting of the Christmas tree outside the courthouse the Saturday after Thanksgiving.
Mill Springs Makers Market is a gift shop on Main Street that feels like a hometown etsy store. Shop for one-of-a-kind jewelry and paper crafts, or take home a handmade holiday wreath and support a local artist.
Historic Eureka Inn, 423-913-6100, $119-$169