Tennessee! Not only is this state home to The Great Smoky Mountains, their famed whiskey, the birthplace of country music, blues, & rock n’ roll, but it’s also home to the majority of Anne’s family! With aunts, uncles, and cousins on one side of the state and our siblings and nieces on the other, this called for a cross-state road trip! Tennessee has 16 self-guided driving routes connecting 95 counties, plus Tennessee Music Pathways, tracing the state’s music history and legends. With plenty of inspiration for our route, we zigzagged from Knoxville to Memphis and discovered so many wonderful off-the-beaten-path places.
On our 10-day Tennessee road trip, we were struck by the volume of historic little towns finding their mojo. From the former mining boomtown of Monterey to the college town of Cookeville, locals all talked about the recent influx of creative people and hip businesses turning their sleepy cities around. Tennessee seems to breed and attract artistic people and their towns are proud to celebrate them. We stumbled upon so many festivals, art workshops, free concerts, and community events that endeared us to these places even more.
See our favorite things to do across the state and start planning your own Tennessee road trip!
KNOXVILLE
With 11 relatives in the Knoxville area, I’ve been coming here for family reunions since I was a kid. Where the French Broad & Holston form the Tennessee River, Knoxville is surrounded by water and nature, so it always played host to our vacations, filled with swimming, hiking, and boating adventures. Though it wasn’t until recently that we started to play in downtown Knoxville. The “Scruffy City” was a little rough around the edges in the 90s and early 2000s, but this town has had a renaissance in recent years. They’ve cleaned up the industrial areas and nurtured 4,500 acres of green and open space. Cultivating talent and creating cultural venues, the city is now one of USA Today’s Top 5 Arts Districts in the country! Urban meets nature, Knoxville has a lot to love.
Staying Downtown at The Oliver Hotel
To fully experience the new and improved downtown Knox, we stayed at the boutique Oliver Hotel right on Market Square. This Southern Living Collection hotel holds its building’s history dear, from its days as a 19th-century bakery, drugstore, dance hall, and ultimately becoming a hotel when Knoxville hosted The World’s Fair. Retaining original architectural elements and decorating with historical touches, The Oliver is a gem! With two top-notch restaurants and one of the coolest speakeasies (hiding under the pseudonym Peter Kern Library) in the building, this hotel is a destination in and of itself.
Market Square
To explore the neighborhood, we took out The Oliver’s complimentary bikes. We cycled through Market Square, lined with beautiful buildings, cafes, shops, and centered around a garden, fountain, and open space to play—be it a game of tag or live music. Kids were splashing in the fountain, buskers were jamming, and diners were loving life on the outdoor patios. I could see why my aunt and uncle just bought an apartment here.
Old City
Heading over to Old City, what used to be known for warehouses, rough bars, and ladies of the night, is now the hippest part of town. We were all about their artisan shops, ethnic restaurants, distilleries, and art galleries in historic buildings. (For a cool souvenir, don’t miss Rala and Bethie Lou’s Fabulous Gift Store). After a drink at PostModern Distilling (one of the 25 distilleries on the Tennessee Whiskey Trail), we went to Kaizen, a fantastic Japanese fusion restaurant (randomly my college-age cousin happened to be there on a date night, so you know it’s cool!). We were going to go home after a full day, but Brother Wolf was throwing a “Jolene” themed party to keep the good times rolling from the city’s recent Dolly Fest, and we couldn’t resist!
Knoxville Locals Tour
The next morning, we met my aunt and uncle to get the locals tour. We started at the 18th-century First Presbyterian Church Cemetery, where all the state’s founders are buried. Nashville may be the capital now, but Knoxville governed the entire Southwestern Territory and got Tennessee to statehood. To deepen our knowledge of the region, we went to the East Tennessee Historical Society & Museum and learned about everything from the city’s Civil War abolitionists’ efforts, the roots of Appalachian music, the top-secret World War II lab that developed the A-bomb, and their favorite hometown girl, Dolly Parton. Just across the street is the Tennessee Theatre. “Oh, you have to see inside,” my aunt Chris exclaimed. “It’s incredible!” The 1920s Vaudeville Theater recently got a 30 million dollar renovation to restore its Moorish Revival architecture and it’s as glamorous as ever, hosting the symphony, Broadway shows, big-act concerts, and 170 days of events each year. Whether you come for a show or the Saturday behind-the-scenes tour, the Tennessee Theatre is a must. And my aunt and uncle’s final Knoxville recommendation? Get on the river.
Tennessee River
Knoxville’s location at the convergence of the French Broad and Holston River isn’t a coincidence, it’s a scenic and strategic spot at the headwaters of the mighty Tennessee River. The city honors those waters with four river parks and dozens of access points. For a perfect nature-meets-urban adventure, we put in our kayak at Ijams Nature Center (also a must), and paddled from forest to skyscrapers. Passing herons, houseboats, and breweries, we tied up our kayak at the banks of the Print Shop Beer Co. We bought a few craft “crowlers” and when we reached the Gay Street bridge, with the sun setting and the city reflecting back at us, we raised a toast to Knox.
MORGAN COUNTY
Frozen Head State Park
Leaving Knoxville, most people go to The Great Smoky Mountains National Park, and often miss Tennessee’s 56 state parks and other glorious mountain ranges. We set out for Frozen Head State Park, which has 14 peaks over 3,000 feet, 24,000 acres of wilderness, and virtually no tourists. We hiked the Panther Branch Trail and in a mile stretch, we reached two gorgeous waterfalls, including Emory Gap Falls framed in a rippled limestone gorge. Back at the ranger station, we learned there are 50 miles of trails and 48 nature programs each month—everything from forest yoga, fire-tower climbs, mushroom identification, to glowworm night hikes. Who knew this state park in remote eastern TN had so much going on!?
Historic Brushy Mountain State Penitentiary
@honeytrek A maximum security prison holding Tennessee’s most ruthless criminals, including the man convicted of assassinating Martin Luther King Jr, is where nobody wanted to find themselves…until now. This century-old jail has reopened as museum, moonshine distillery, and restaurant behind bars. Take a swig of the End of the Line Moonshine and get ready for a tour given by a former prison guard…it’s an experience you aren’t gonna believe! #visittennessee #partner @tennesseevacation ♬ original sound – HoneyTrek
Another fun fact about Frozen Head? Their river water is captured for Frozen Head Vodka, made at the nearby Brushy Mountain Distillery and former petitionary! No joke, a 100-year-old prison, that held some of Tennessee’s most notorious criminals (including James Earl Ray, sentenced for the assassination of MLK) is now a museum, concert venue, restaurant-behind-bars, and moonshine distillery. Well, that sounded intriguing enough, so we paid the Historic Brushy Mountain State Penitentiary a visit. We made the video (above) to do this bizarre and oddly moving place justice.
MONTEREY
It was Tuesday, the perfect day to visit Monterey, TN. Each week of the summer, this little town tucked in the Cumberland Mountains hosts one of the best bluegrass jam sessions you can find in the Appalachians, “Pickin at the Market.” We pulled up to the farmers-market-meets-concert venue, cued up with amps, mic stands, and camping-chair seating. Musicians come from far and wide for this convergence of fiddlers, banjo players, guitarists, upright bass players, and Appalachian bluegrass singers. Like Tater, who has won multiple banjo competitions, and Jill who’s played violin at Carnegie Hall, and the event founder Terry, who can play five different instruments without skipping a beat. Without sheet music or a set list, it was incredible to hear these dozen musicians, ranging from ages 18 to 80, riff, harmonize, and break out in clogging dance moves.
Passionate locals are revitalizing this sleepy town. Walking the main street of this former coal mine town, there isn’t much at first glance…but eat at the farm-to-table Ben Anna’s Cafe, tour the Monterey Depot Museum with Dale or Rafferty (what storytellers!), and stay at the brand-new Spacious Skies Belle Ridge glamp-ground, and you’ll see this town is on the rise.
Things to Do in Monterey, TN
They say Monterey is “where the hilltops kiss the sky,” and we felt that when we hiked right from our campsite to Bridal Veil Falls and went to the Bee Rock Lookout to take in the sweeping views of the Cumberland Plateau. Come to Monterey to hike the limestone gorges, pay homage to their 4,000-year-old Mound Builders at Standing Rock Park, and catch Pickin’ at the Market every Tuesday, as Terry says, “from spring until our fingers get cold.”
COOKEVILLE
Continuing along the Promised Land Scenic Byway and the route of the state’s earliest settlers, we reached Cookeville. This town is home to Tennessee Tech and the fun college vibe immediately came through—especially in the Historic Westside District! We turned into the municipal parking lot, framed with an archway of two dozen bicycles welded together by a local artist. Walking Broad Street, cute boutiques literally beckoned us—from #Holly’s window sign saying “Hello Gorgeous, come on in!” to Glass Tangerine’s plant shop greeter, Elsa the adorable Labrador. And when we saw Red Silo, an actual grain silo turned into a brewery, we had to go in for a flight of their award-winning beer.
Best Eats in Cookeville
So many restaurants came recommended in Cookeville…Putnam Room, Seven Senses, Mauricio’s Italian Restaurant…it was tough to pick! We went with Father Tom’s for its cozy vibe and great veg options (who knew ricotta could be vegan? Yum!). The pub gets its name because the owner was a beloved professor at Tennessee Tech for so many years, that everyone just called him Father Tom. For dessert, we went to Ralph’s Donuts, a Cookeville institution making sure glazed fried dough is available into the wee hours…good man! Ice cream lovers, don’t miss the iconic Cream City!
Burgess Falls State Park
Just south of Cookeville is the fantastic Burgess Falls State Park. When we saw a photo of this 136-foot waterfall that comes to a point and cascades in three directions, it reminded us of the cover of National Geographic’s Rarely Seen! It’s a truly unique waterfall, made even cooler by the fact that you can kayak right to its base. We put in at Cane Hollow for a four-mile river trip, in a quiet canyon with jumping fish, darting King Fisher, and submerged forests. The roar of the falls drew louder and the limestone cliffs grew higher, and there she was…prettier than any photo could do justice. To its benefit, Burgess is not a rager, which means you can actually see the stunning rock formations behind the white curtain and get close enough to play in its current like a water park. We’d highly recommend this paddling trip, so if you don’t have your own watercraft, head out with Kayak Adventures of Tennessee. This eco-conscious outfitter also incorporates river cleanups into their trips, gotta love that! Not a paddler? The state park also has a trail to the falls overlook.
SMITHVILLE & CENTER LAKE
Buddy the Camper followed the river towards Smithville and Center Lake, where we had a reservation at a killer A-frame cabin overlooking the water. After a day of adventures, we could not have been happier just chilling on our forested patio with its firepit, hot tub, and BBQ and having a party for two. The cabin was decorated beautifully and our bedroom, with panoramic windows and spa-like bathroom, was divine. (If this vacation rental is booked up, the owner also has treehouse nearby!).
Downtown Smithville
After watching a gorgeous sunrise view from bed, we headed into the center of Smithville. Walking around Walnut Street, we popped into so many cute shops, like the Refined Boutique, Cheryl’s Beau Bees, and The Male Room Brotique, but the wild part is…they all opened in the past two years! Like many of us during the pandemic, these people realized life is too short to not do what you love…and they chose little Smithville as the perfect place to do it. Like Karen and Rick who turned an old mechanic shop into The Arts Garage, a place where they can create and teach art. “There is a maker in all of us,” Karen told me, “so we’ve created affordable classes and kits for anyone to get involved.” All the shopkeepers could not have been friendlier or more passionate about their small businesses—because they were all fulfilling a dream.
Fiddlers Jamboree
Smithville, while a small town of 5,000 people, goes all out in the name of the arts and a good time. For the past 52 years, they’ve hosted the Fiddlers Jamboree with 35 music and dance events and streets full of hand-made crafts, and food booths galore. The event draws ~100,000 people…and apparently, more of them are staying for good.
The Appalachian Craft Center
This Tennessee Tech campus is dedicated to the traditional Appalachian arts of blacksmithing, ceramics, weaving, glassblowing, woodworking, and its digital interpretations. Mid-century wooden buildings tucked in the forest, with craft rooms and bunkhouses, this place felt a little like a summer camp…and we wanted to enroll! After a walk through their series of art galleries and excellent boutique, we peeked into the glassblowing studio. As luck would have it, Professor Brock and Artist in Residence Tabitha were at work. Watching Tabitha dip into the molten glass, blow it into an orb, shape it against the steaming wood, and create art in a matter of minutes was mesmerizing. If you want to try your hand at any of these timeless crafts, the Appalachian Craft Center hosts weekend workshops for all skill levels.
DICKSON
Road-tripping Tennessee, we saw festivals at every turn! Knoxville’s Dolly (Parton) Fest, Smithville’s Fiddlers’ Jamboree, and now the Dickson Street Festival! This historic town, 45 minutes west of Nashville, throws it down each year with 100 booths, 25 food stalls, and 15 bands across 4 stages, plus fireworks! And what made it even more fun? We got to be part of the festival! Reading Rock Bookstore heard we were coming to town and asked us to do an author signing of Ultimate Journeys for Two and Comfortably Wild. We met so many nice people at our booth, strolling the streets, and dancing the night away in this great little town.
What to Do in Dickson, TN
Even if you can’t catch the June street festival, Dickson has got plenty going on. You could visit the state historic site of Clement Railroad Hotel Museum, take a paint and sip class at Wild Blue Yonder, get really good tacos & margs at Desert Rose Cantina, learn to make soap at Buff City, and catch live music at 119 Craft Brewery. Just outside of town, Sweet Charlotte is a candy lovers and Instagramer’s paradise with their old-time displays. For a little adventure, kayak the Spillway at Montgomery Bell State Park. The park also has cute cabins if you want to stay in nature but still near town.
Bonus Town: Franklin
Just 36 miles southeast of Dickson is one of the most charming and sustainable towns in the USA…Franklin, Tennessee! Founded in 1799, this pristine place has accomplished the rare combo of National Historic Register of Places and LEED-certification…citywide! We were so inspired by our visit we wrote this in-depth guide.
HENDERSON & STILLWATERS FARM
When researching our glamping book, we fell in love with the simple charms of farmstays and we now make them a part of our trips whenever we can! When looking for one in Tennessee, Stillwaters Farm and Winery in Henderson totally jumped out at us. With its classic red barn, framed under a 200-year-old oak tree, pastures with happy horses and miniature donkeys, rows of Chardonel vines, and a secluded farmhouse cottage for guests, it’s a truly idyllic place. Funny enough, the proprietors Valeria and Rich, aren’t farmers or winemakers by trade; he’s a fiber optics consultant who just really likes driving tractors and she’s a school teacher who wanted to learn a new way of life and share the experience with guests.
@honeytrek Hiding on the bucculoic Stillwaters Farm in western Tennessee, there’s a pirate winery. And when we say pirate, a descendent of Blackbeard is trying her hand at winemaking—bootleg and island-style. Using tropical fruits, flowers, and herbs and aging them in whiskey barrels, Capn’ Val is throwing out the rules and making surprisingly good wine in the shadows of her garden shed. As of summer 2023, 40 Cannons Winery’s silo-tasting room is open to try wines like Bleedin’ Hearts, Wild Rose, and The Revenge…if you dare! @tennesseevacation #partner #madeintn #stillwatersfarm #winery ♬ The Wellerman (Sea Shanty) – Instrumental – Tik Tak Tok
We knew Stillwaters Farm’s latest endeavor was Forty Cannons, but little did we know that the inspiration behind this pirate-themed winery is Valeria’s ancestor…the infamous Blackbeard. Channeling that renegade spirit and island style, Capn’ Val is using tropical fruits, flowers, and herbs and aging them in rum barrels. In her grain silo-turned-merry tasting room, we got to try creative infusions with cheeky names like Queen Anne’s Revenge and Scurvy Dog. We had `never tried wine infused with rose petals, basil, or key lime, and couldn’t believe how good they were! That night, sitting on our cottage patio, watching the fireflies glow and listening to the crickets’ chorus, our love for farmstays grew even more.
What to Do Around Henderson, TN
The small but colorful town of Henderson is just 15 minutes away from Stillwaters with some lovely old buildings, like the Chester County Courthouse, the hip UrbanHouse espresso bar & bistro, Sue Shelton White Park, and a monument to their hometown music legend, Eddy Arnold! For more adventures in the area, Chickasaw State Park has a beautiful lake perfect for swimming and trails, including an impressive boardwalk that lets you walk straight across the water.
MEMPHIS
The last stop on our Tennessee Road Trip…our beloved Memphis! With my sister, bro-in-law, and nieces living here for the past for 10 years, we’ve visited upwards of 20 times and have grown to know and love Grind City. More than Graceland, Beale Street, and BBQ, we’ve got all sorts of tips for an authentic trip to the home of the blues, soul, and rock n’ roll. Read this dedicated travel guide to exploring Memphis like a local!
Why Do People Love Tennessee So Much?
After 10 days and 500 miles, traveling the backroads from Knoxville to Memphis, we connected two great American cities and discovered so many fantastic little towns, beautiful wilderness, and genuinely lovely people along the way. Little moments of serendipity seemed to happen on the daily, like spotting that Five & Dime hidden in the ivy, that impromptu glassblowing session, the farm dog that became our new best friend, or late-night clogging with the Monterey Pickers. We’ve been to all 50 states and can say Tennessee has a strong sense of place and one worth being proud of. TN has world-famous attractions, but take your time to ramble along the backroads and you’ll find the best-kept secrets.
Many thanks to Tennessee Tourism for inviting us to their state and supporting our storytelling! To show our gratitude to the lovely people and places in this state and continue our HoneyTrek Cares initiative, we’ve donated to the following nonprofits: Tennessee Scenic Rivers Assocation for protecting the waterways, Tennessee Trails for championing outdoor access and inclusion, and Knowledge Quest for building strong communities!
Have any questions about this Tennessee road trip itinerary? Drop them in the comments!
