Jonesborough: The Town From A Storybook

Christmas had arrived in Tennessee’s Oldest Town and I was lucky enough to experience it on the coldest Saturday of the season thus far. Needing a little warm up, I opened the front door to the cozy Corner Cup, the most charming coffee shop in town. I perused the colorful menu and decided on a gingerbread latte and a side of toast with banana and peanut butter.

A gingerbread latte and a side of toast topped with peanut butter and banana from a local baker.

I unbuttoned my wallet to slide out my debit card and pay for my breakfast and realized it wasn’t in its usual slot.

“Oh no! I don’t have my debit card!”

“Well, are you local?” The barista behind the counter asked me.

“I am,” I replied.

“Then in that case I’ll start you a tab and you can pay next time you come in.”

I thought this only happened in those novels that take place in small fictional towns where people ride their bikes to the farmers’ market and wave knowingly at all the people they pass. What I found out, was that Jonesborough most definitely is one of those storybook towns.

As I sat down to enjoy my latte in the eclectic dining room, I savored my side of toast, topped with bananas and homemade from a local baker. The Corner Cup offers a menu of bagels, specialty toasts, brewed coffee, lattes and a host of more goodies. But most importantly, they extend to you a good cup of friendliness and honesty. A perfect start to a day experiencing Christmas in Olde Jonesborough. My next stop was a tour through downtown with a seasoned pro.

My downtown tour guide, Bob, dressed in vintage style clothing in front of the Chester Inn Museum.


The shops and businesses that make up downtown Jonesborough are filled to the brim with history, and it’s absolutely fascinating! I took an in-depth tour back in time with a knowledgeable guide from the famous Chester Inn Museum. I soaked in plenty of little intricacies of everything from the iron trim around some of the door frames of downtown buildings, to how many times the town has caught on fire (and which building has never caught on fire). My particular tour guide was dressed to the nines wearing a festive top hat with a pluck of holly. He very passionately told us of the trials and errors of his beloved town including stories of Andrew Jackson, which building was the town’s telegraph office, more recent history regarding the world renown International Storytelling Center plus detail after detail about this fascinating town. I felt like I was turning back the pages of Northeast Tennessee’s history book in this lovely place.

For the current holiday season, Christmas in Olde Jonesborough takes place every Saturday in December until Christmas. On this particular Saturday, the streets were filled with young children and their parents, snapping photos with characters from the holiday classic The Grinch, visitors “shopping small” with the unique shops and restaurants which line Main Street. The smell of fresh popped popcorn wafted down the sidewalks, luring families into the well-loved Lollipop Shop. Music played softly in the background of the holiday cheer, and memories were being made all around me.

After shopping, strolling, touring and watching all the joy take place in my midst, I realized it had been a few hours since I ate. With lots of different places to eat on Main Street, I decided to eat at a local restaurant of the same name: Main Street Cafe.

Kielbasa Stew, a not so basic grilled cheese and chocolate pie from Main Street Cafe.

As I walked a couple steps up and into the front door, I was greeted with smells that reminded me of Christmas during my childhood. Warmth and hospitality are well practiced in this town, and at this restaurant. The young people working behind the bakery case assisted in my very difficult decision making. I finally picked their Kielbasa Stew and a not so basic grilled cheese sandwich. Of course, dessert was necessary. So after gazing at all of the lovely choices behind the glass, I picked a classic Chocolate Pie.

Every inch in the Main Street Cafe is beautifully preserved. Your eyes are drawn up to the high ceilings, and all the way down to the original creaking wood floors. One cannot seek a place without history in Jonesborough and find one. This was certainly a lunch well savored.

My midday meal put me in a state of calm and satisfaction, and my head was still reeling with the beauty and culture of the Oldest Town in Tennessee and the Storytelling Capital of the World. But just one more stop was in order.

The Pineapple Upside Down Cake would have been a delicious dessert sipper on its own. But the Dark Roast was my favorite from Tennessee Hill Distillery.

Right across the railroad tracks, situated next door to the oldest private home in Jonesborough, is a new distillery built into an old salt house. The train chugs past over a dozen times a day, lending to the character of the distillery. The raw wood throughout the distillery felt cozy and rustic. I was greeted by the welcoming employees and the owners themselves, coaxing me to come and sample their flavored whiskeys and bourbons from Tennessee Hills Distillery. I’m not much of a liquor drinker, but I let myself taste a few of their favorites. Lemon Drop was a surprising flavor, made with real lemon juice so it doesn’t have the taste of artificial sweeteners. The Pineapple Upside Down Cake would have been a delicious dessert sipper on its own. But the Dark Roast was my favorite. It was delightfully coffee infused but not so strong it puts hair on your chest.

Well fed, well taught and warm with whisky in my belly, I drove home with a new appreciation for Historic Jonesborough. My day was drawing to a close, but the heart of Jonesborough will always be beating.

For information on what to do, where to eat and more in Jonesborough, go to www.jonesborough.com.