Historic Jonesborough: Tour the Oldest Town in Tennessee

The minute you set foot on Historic Jonesborough’s Main Street, you feel a sense of place. Brick storefronts lined up under the watchful eye of the courthouse clock. People greet each other on the way to work or they gather for coffee and a sandwich at lunch.

Jonesborough is Tennessee’s oldest town, so people here have had a long time to build a sense of community. Perhaps the town’s frontier heritage established a tradition to know the neighbors and look out for each other.


Fortunately for the visitor, the town’s embrace extends to everyone who comes by. With flower boxes decorating sidewalks, American flags flapping in the breeze, and shop windows tempting you to step inside, Jonesborough is a pleasant destination.

A trusting, relaxed attitude is pervasive here. A shopkeeper asked a couple to mind the store for just a minute. She needed to slip into the restroom. “Just make sure no one walks off with the cash register.” At a specialty shop a few door down, the shopkeeper was apparently running an errand, but left the door open so I could look around. One locked business had a “Gone Fishing” sign.


Small businesses feature an enticing selection of antiques, collectibles, home decorating items, toys, glass art, quilts, crafts, jewelry, and weekend apparel. The best place to indulge is Earth & Sky Confections where artisan chocolates are beautiful works of art and unbelievably delicious.


Beginning in May, free musical entertainment attracts a congenial crowd to the sidewalks in front of the Washington County Courthouse. Music may be bluegrass, Celtic, jazz or old-time blues. To mix things up a little bit, performance artists and storytellers join local and regional bands on the stage. Traffic is blocked off so lawn chairs can spill into the street. This free entertainment begins at 7 p.m. every Friday night through September.

Jonesborough Days, a July 4 holiday extravaganza, features a parade, Civil War encampment, Native American village, craft, live entertainment, food vendors, and fireworks.


The biggest event in town is the National Storytelling Festival produced by the International Storytelling Center in the heart of Jonesborough. Locals feel a tremendous ownership of the festival, and take lots of pride in the high caliber of storytellers who spin their tales to audiences large and small. Early ticket sales indicate attendance will be very good this year. More than 100,000 people are expected to attend each year.

A Teller-in-Residence program almost guarantees visitors will hear a story when they come by the International Storytelling Center. From ghost stories to traditional tales, stories are woven.


Jonesborough has other entertainment venues, such as the favorite Jonesborough Repertory Theatre. You might want something simpler, like playing bocce or listening to bluegrass at the Depot Street Brewing Co. This local brew pub sells a flavorful selection of craft beers to enjoy in casual indoor and outdoor tasting rooms.

For dinner, locals directed me to The Dining Room at the old Town Hall building for fine Cuban-influenced cuisine. The empanadas, asparagus soup and Cuban sandwich I ordered had some tasty seasoning. I had an equally pleasing meal earlier in the day at the Main Street Café. It attracts a jubilant luncheon crowd because of its sinfully rich brownies and pastries, the perfect dessert to their wholesome sandwiches, salads, quiches and soups. Submarine sandwiches, burgers, milk shakes and root beers are served at the Jonesborough General Store and Eatery.


Hospitality in Jonesborough dates back to the era of John Sevier, Tennessee’s first governor. Main Street was once the Old Stage Road, a vital connector from the frontier to older settlements. The renovated Historic Eureka Inn hosts overnight guests, as does the cozy Blair-Moore House, a bed and breakfast with great charm and award-winning breakfasts. Visitors can glimpse history at the Chester Inn, also on Main Street, which now serves as a historical museum with a very knowledgeable guide who leads tours through the second floor guest suites. Andrew Jackson, James K. Polk and Andrew Johnson, all destined to become U.S. presidents, slept here.


A descriptive map for a walking tour of Jonesborough’s historical sites can be picked up at the Historic Jonesborough Visitors Center. In addition to an information desk, it has a small heritage museum and gift shop.

Have you experienced Historic Jonesborough? What stood out?

Hi! I’m Linda Lange. As a travel writer living in Knoxville, I fully appreciate barbecue, bluegrass and Dollywood. My...Read on


  1. Pingback: Write Your Next Chapter at Storybrook Farm | Tennessee Triptales

  2. avatar


    I feel like you captured the community feeling of Jonesborough. Thank you for sharing this.


    Nathan Kiger

    Tank you for taking my email and I hope that you are having a good day can u help me and my class learn about this town. I used to live here and I hope that you can help me learn


    Nathan Kiger

    I used to live here


    Sandra Gurrola

    Hello our family will be visiting Jonesborough Mid September, are there any Rentals, Cabins or Hotels around the area that you can recommend?

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