Apr. 26, 2022 – Among the prettiest little towns in East Tennessee, Jonesborough was once the end of civilization. That messy business with the British was settled, and the nation’s westward expansion was burgeoning. Intrepid pioneers waylaid in Jonesborough, the last stop on the stagecoach line, to form caravans and stock up on provisions before continuing their journeys.

Jonesborough, about 90 miles northeast of Knoxville, is the state’s oldest town. It was founded in 1779 as part of North Carolina before Tennessee became a state in 1796. The population today numbers about 5,400.

The town’s historical legacy is entwined with links to both sides of the Civil War. Although Tennessee joined the confederates, public sentiment in these parts was largely abolitionist. The country’s first periodical dedicated to eradicating slavery was published here.

Jonesborough makes modern-day history as the Storytelling Capital of the World. Now celebrating its 50th year, the National Storytelling Festival celebrates the Appalachian tradition of storytelling. The three-day festival, held the first full weekend in October, brings together acclaimed tellers who spin wondrous tales, and thousands of captivated listeners from around the globe.

Storytelling performances and events are also held during the year at the International Storytelling Center. (Left) Mary B. Martin Storytelling Hall at the International Storytelling Center in Jonesborough.

Let me tell you the story of my visit to Jonesborough, Tennessee.

Jonesborough Town Tour

I had only a day to see, do, and learn as much as I could, so I signed up for a guided tour at the Chester Inn State Historic Site and Museum. It’s the oldest commercial building in town, built in 1797 as a fine hotel on the stagecoach line. Several United States presidents slept here, including Andrew Jackson and James K. Polk. After numerous additions, iterations, and renovations, it opened as a history museum in 2011.

Within the museum’s collections are artifacts, displays, and photographs that trace the history of Jonesborough from its inception.

You can also view the upstairs parlor, dining room, and lodgings restored to the Victorian era. (Right) Chester Inn State Historic Site and Museum.

On the Jonesborough Town Tour, a costumed interpreter – Bob, in my case – guides you while relating the town’s colorful past and a litany of fun facts. The building stock is an architectural conglomeration of Federal, Greek Revival, Italianate, Craftsman, and other styles, depending on who built it and whence they came.

A 1777 log cabin, relocated to Main Street, is where a young Andrew Jackson lived and practiced law while awaiting a caravan.

According to local legend, his ghost occasionally appears near the cabin or walking toward the old courthouse. (Left) Bob, a costumed tour guide, in front of Christopher Taylor House, a log cabin built in 1777.

The brick sidewalks that line beautifully preserved Main Street are not the originals. Those were pulled up in the 1930s and replaced with concrete as a modernization project. Then, when the downtown area was listed on the National Register of Historic Places in 1969, the concrete was removed, and bricks were laid to bolster the ambiance of yesteryear.

I was curious to note an L-shaped chunk of stone (right) standing at the curb. Turns out, it’s a mounting block, or carriage step – a stair step that helps passengers climb in and out of a carriage or stagecoach.

It was time for me to explore on my own, and I started with lunch.

Main Street Café

Located in the town’s 1930s post office building, Main Street Café is a charming lunch spot decked with a pressed-tin ceiling, hanging globe lamps, and other original architectural features. The menu features homemade soups, salads, quiches, and an array of burgers and grilled sandwiches. Chicken and tuna salads are house specialties, and the desserts are just like Grandma used to make.

Historic Eureka Inn

After topping off my lunch with a yummy slice of coconut cream pie, I checked into the Historic Eureka Inn, an elegant boutique bed-and-breakfast. The two-story structure was built in 1797 as a private residence, and later became a boarding house. The first bathtub with hot and cold running water was added in 1910.

Today, the Historic Eureka Inn is impeccably restored with 13 uniquely decorated sleeping rooms with private baths, gracious lounging spaces, and front-and-back porches appointed with rocking chairs. Photo provided by Town of Jonesborough.

In the back yard is a spacious courtyard with a gazebo and organic gardens.

Innkeepers Blake and Katelyn Yarbrough offer the height of hospitality, making sure I had ample beverages, wi-fi, and directions to local interests.

Katelyn led me to my room, named The Maxwell Room for a previous owner in the 1850s. It was a vision of Laura Ashley-inspired sweetness, awash in tints of green and coral, with a queen-size four-poster bed, armoire, and writing desk. The botanical wallpaper matched the pillow shams, dust ruffle, swaggy window valances, and shower curtain, while a contrasting coral mini-print wrapped the bathroom.

Strolling on Main Street

As a shopping maven, I decided to explore the retail establishments carved into the historic architecture. The brick-lined sidewalks are dotted with park benches and urns planted with festive flora.

More discoveries were The Lollipop Shop, a colorful boutique loaded with retro toys and candy from your childhood; Jonesborough Antiques & Artisans, a multi-level warren of all things vintage and then some; and Gabriel’s Christmas, a year-round emporium of holiday trees and bling.

I really wanted a cute wooden stool at the antique store, but limitations of carry-on luggage persuaded me to buy a Christmas tree ornament as a souvenir instead. (Right) Jonesborough Antiques & Artisans on Main Street.

I also walked around the Old Jonesborough Cemetery, mainly because I’m the kind of person who does that sort of thing. It was a community burial ground established about 1800 and in use through the mid-20th century. Many of the town’s early movers and shakers were laid to rest here.

Tennessee Hills Distillery

Across the railroad tracks that parallel Main Street is Tennessee Hills Distillery, housed in the red brick Salt House, built in 1840 to store salt. The building was empty for 20 years before chemists Stephen and Jessica Callahan transformed it with a combination of Appalachian scrappiness and recipes, and distillation methods carried to America by their Irish forefathers. Among the offerings are about 15 liquors – including S.E. Callahan’s straight bourbon whiskey with hints of smoky oak, vanilla, and honey – and Tennessee Hills pecan pie rum spun from molasses.

In the garage is the taproom, where you can choose from a revolving menu of mules, shots, and creative cocktails. (Left) Tennessee Hills Distillery on Fox Street.

Texas Burritos & More

A local favorite, Texas Burritos & More boasts generations of family recipes infused with Tex-Mex flavors and spices. The casual eatery is known for burritos, which you can tailor with meats, fillers, add-ons, and heat. My beef enchiladas were satisfyingly seasoned, smothered with chili con carne and queso, and topped with shredded cheese and generous sprinkles of more beef. Rounding out the platter were cowboy beans, rice, lettuce, and tomatoes.

Depot Street Brewery

After dinner I stopped by Depot Street Brewery, Northeast Tennessee’s first brewery, for a tasting. The venue is a rustic indoor-outdoor space with pinball machines, firepits, a bocce ball court, and, usually, a nearby food truck. The microbrewery’s rotating roster includes lagers and India Pale Ales.

Most popular are the flagship Loose Caboose, a German-style lager, and Freight Hopper, a malty IPA. (Right) Depot Street Brewery.

Farewell to Jonesborough

After a luxurious night’s sleep at the Historic Eureka Inn, I checked out early to move on to my next adventure. First, I was treated to a Southern-style breakfast in the dining room. I was expecting simple prefab fare like those at so many hotel chains. However, when Innkeeper Blake offered made-to-order eggs Benedict, I wasn’t about to refuse. An epicurean start to a new day!