Cherohala Skyway Challenge

Discover the allure of Tennessee's most-visited state park, Fall Creek Falls State Park, which is home to Tennessee's tallest waterfall and a vast 30,000-acre wilderness. This route offers the best of both worlds: rolling roadways and dedicated trails within the park, as well as picturesque country roads beyong its borders. Plan to ride on weekdays or early mornings to savor the tranquility and natural beauty of this state park treasure. (less)

The Cummins Falls Out-and-Back is a low-traffic ride that you can easily combine with a trip to beautiful Cummins Falls State Park. The park makes a great place to start, not only because of the first-class visitor center and large parking lot, but also because it’s a beautiful place to explore after the ride, with both an easy walk to the overlook and a more involved hike down to the gorge and the swimming hole below the waterfall. The ride is relatively short, so you’ll have plenty of time to enjoy the park afterwards. (less)

Beautiful scenery, fun roads, and a ton of climbing (some of which is quite steep) add up to make this ride both challenging and rewarding. The ride starts at Sgt. Alvin C. York State Historic Park, which pays tribute to one of the most decorated soldiers of World War I, while also providing access to the historic York farm and homestead. (less)

For those craving an authentic West Tennessee cycling experience, look no further. This ride offers low-traffic rural roads and wide open farm fields, showcasing the state's agrarian charm. (less)

This historic landscape is one of the best places to ride in West Tennessee, offering a unique glimpse into the region's past. Shiloh National Military Park was the site of an epic struggle during the Civil War, with nearly 24,000 casualites. Nearby, Shiloh Indian Mountains National Historic Landmark preserves the site of an ancient cheifdom and earthen mounds. Don't miss the opportunity to pause at interpretive markers - you might even want to take a second lap to fully appreciate this unique mix of history and culture in Southwest Tennessee's natural landscape. (less)

The Middleton Loop is a fun little ride on some curvy low-traffic backroads through Southwest Tennessee's agricultural landscape. A few wooded climbs and descents will be rewarded by a post-ride meal in Middleton, Tenn. (less)

Some of the best riding in East Tennessee can be found in the Sequatchie Valley. That's why you'll find not just one, but three routes, each offering a unique perspective on the valley's geography and charm. The Middle Sequatchie Valley Loop begins with beautiful views from the Cookie Car Cafe in Dunlap and heads north through Sequatchie County, featuring historic sites, off-the-beaten-path attractions, and georgeous views of Walden's Ridge and the South Cumberland Plateau. Pair this route with the Upper and/or Lower Sequatchie Loops for a multi-day riding expedition. (less)

A suburb of Chattanooga, Signal Mountain offers scenic views with the convenience of urban ammenties. This route features undulating roadways with some of the best overlooks of the Chattanooga region. (less)

The Monkey Town Loop starts and ends in historic Dayton, Tenn., home of the highly publicized Scopes Trail, aka "Monkey Trial," of July 1925. This route is a monumental challenge, featuring two notable climbs: Brayton Mountain and Evensville Mountain. While both are challenging, Evensville takes the nod as the harder climb due to a steeper average grade leading up Walden Ridge. Enjoy this challenge, with its scenery and history, and a fabulous ending at Monkey Town Brewery. (less)

The Lynchburg Loop challenge starts in historic downtown Lynchburg, Tenn., best-known as the home of Jack Daniel’s Distillery. This scenic ride through Lynchburg's rugged landscape has some steep grades and challenges, but the reward is ending the ride at some of Tennessee's most renowned attractions, including a distillery tour and a meal at any number of famous Lynchburg restaurants. (less)

This challenging loop route launches from Mousetail Landing State Park on the Tennessee River in Middle Tennessee. This 40-mile loop offers up several short, steep climbs, with some steller wooded sections that make all the climbing well-worth it. (less)

Don't be fooled: Minor Hill Loop is named after the nearby town of Minor Hill, not because this route has minor hills. Expect undulating roadways and challenging climbs on this loop route, but you're in for a real treat as this ride is loaded with beautiful rural scenery and tree-covered country lanes. (less)

Explore the captivating history of Reelfoot Lake, a shallow natural lake that formed when the Mississippi River ran backwards during the New Madrid Earthquake in 1811-12. Today, the area serves as a bird sanctuary, with the largest wintering Bald Eagle population in the eastern U.S. Explore this fast and fun ride around one of West Tennessee's natural treasures. (less)

This 55-mile loop launches out from the scenic Carroll County Thousand-Acre Recreational Lake in Huntingdon, Tenn. - the largest man-made lake in West Tennessee - and heads east to explore Natchez Trace State Park and Forest. Enjoy the variety of lakes and rural scenery along the way, but know that this route takes some serious effort with its series of short, punchy climbs. (less)

This scenic route rambles along the scenic Upper Clinch River in Kyles Ford, Tenn. Sections of this river and landscape are under the care of the Nature Conservancy of Tennessee and other state agencies and conservation groups concerned with protecting the rare and endangered species that abound there. Watch for bald eagles and other wildlife as you ride alongside the river. While the scenery along this route is more than enough to warrant the trip, there's plenty of other attractions and adventures to explore in the area. River Place on the Clinch River serves as the perfect starting point for this riverside ride - they offer cabin and river rentals. This scenic route rambles along the Upper Clinch River in Kyles Ford, Tenn. Sections of this river and landscape are under the care of the Nature Conservancy of Tennessee and other state agencies and conservation groups concerned with protecting the rare and endangered species that abound there. While there, make time to float the Clinch River and hike the Kyles Ford Falls trailhead. (less)

The Goshen Valley Loop traverses two picturesque valleys, with a mix of climbing workouts and scenic strolls. There's a serious climb at the halfway point as you make your way over the ridge that separates these two valleys. The beauty of East Tennessee's rolling hills and valleys will have you coming back for more. (less)

The Watauga Lake Winery Loop winds through the rural landscape of Johnson County, in the northeast corner of Tennessee, at the border of North Carolina and Virginia. This route is a relatively short ride, but it's a solid workout with plenty of climbing for the distance. The ride includes a great mix of scenery, including a section that follows Watauga Lake, as well as several creekside rambles. At the end, enjoy visiting two award-winning Tennessee wineries: Watauga Lake Winery and Villa Nove Vineyards. (less)

Cumberland Gap - named for the historic mountain pass behind the town where Tennessee, Kentucky and Virginia meet - is a charming little mountain town with stunning views and an ancient history. It’s also a great place to bike. The Cumberland Gap Loop heads south from town and runs parallel to the Cumberland Mountains, providing some fantastic vistas of this impressive mountain "wall." (less)

Ride 18 miles alongside the swift and cooling waters of the Tellico River through the Cherokee National Forest on the Tellico River Out-and-Back. Because this route is an Out-and-Back that runs upstream, it works for cyclists of any level. Whenever you feel fatigued, just turn around and let gravity help you roll back to where you started! (less)

Want to ride like a local? Look no further than the Townsend Out-and-Back, which offers a delightful escape from the area's more difficult climbs. Old Walland Highway boasts a gentle, rolling terrain with just one short climb. This "easy rider" route follows the Little River most of the way. Shorter in distance, the Townsend route is perfect for cyclists seeking a relaxing escape with stunning scenery. Ride like a local and explore this peaceful gem in the heart of the Smokies. (less)

The Mississippi River Ramble offers the exhilarating experience of biking across the mighty Mississippi River from Memphis, Tenn., to West Memphis, Ark., along Big River Crossing, a bike/ped walkway attached to the historic Harahan Bridge. Beginning at the Tennessee Welcome Center in downtown Memphis, this route explores the Memphis River Parks system, Big River Crossing, Mud Island River Park and the new urbanist-style neighborhood of Harbor Town. Soak in the culture and history of the Mississippi River as you expore the Memphis riverfront by bike. (less)

Located just 30 minutes from Memphis, the tiny town of Moscow, Tenn., feels worlds away from the hustle and bustle of the big city. This loop ride features rolling rural roads, very little traffic and tranquil landscapes. (less)

The Ripley - Henning Loop is a surprisingly hilly ride, defying the typical notion of West Tennessee's flat terrain. Experience a variety of scenery along this route, from expansive farmland to dense woodlands, with challenging climbs and fun curvy stretches. The route runs along the edge of the Chickasaw National Wildlife Refuge, which is located along the Mississippi River and is the largest tract of bottomland hardwood forest in Tennessee, as well as the small towns of Ripley and Henning. If you have time, stop by the Alex Haley Museum & Interpretive Center in Henning, the boyhood home of author Alex Haley. (less)

While 31 miles and 2,000 feet of climbing may not seem that intimidating, the climbing packs a punch with plenty of double-digit grades. But conquering the challenge of these steep pitches is well worth it. You'll be rewarded with some fantastic stretches ranging from narrow tree tunnels to wide-open farmland to ridgeline vistas. (less)

This route has it all - beautiful wide-open ranchland and tree-lined ridge roads, challenging climbs and fast descents, smooth pavement and bumpy chipseal. It also includes 13 miles of the Natchez Trace Parkway. The variety on this ride is fantastic, but be advised that quite a few of the climbs are super steep, with grades reaching close to 20%. Despite these challenges, we highly recommend this route, as it showcases everything that Middle Tennessee has to offer in one beautiful ride. Starting at Historic Leipers Fork is an added bonus - this tiny community is centered around the immensely popular Fox & Locke restaurant and music venue. Leipers Fork also has a couple of art galleries, a spa, and a wine-tasting room featuring local wines. (less)

The Land Between the Lakes National Recreation Area gets its name from the two lakes, Kentucky Lake and Lake Barkley, that form the west and east boundaries of the park. Visitors can enjoy camping, paddling, hiking, biking and fishing, as well as attractions like a planetarium and a living history farm. Bison and elk were reintroduced to the area and can be spotted in designated areas. The main north-south roadway through the park (TN-49) is designated as the Woodlands Trace National Scenic Byway and a joy to experience on bike. Cyclists can explore the scenic byway, mountain bike trails and gravel roads. The park gets busy during peak travel times and holidays. For a quieter ride, weekday mornings during the off-season are recommended. (less)

The Liberty Challenge route packs a punch! With over 2,400 ft of elevation gain concentrated in two steep climbs, this route will test any cyclist's grit and stamina. But the effort is rewarded with stunning scenery along quiet roads and a couple of exhilarating descents that leave you wanting more. This route is a physical challenge and a scenic escape – pure cycling bliss! (less)

Don't let the distance fool you – the Dale Hollow Ramble is no easy spin around the lake! For those who love a challenge, the climbs are rewarded with incredible scenery. Get ready to conquer those climbs and soak in the beauty of Dale Hollow Lake. (less)

The Rock Island Loop offers a solid workout paired with post-ride outdoor adventure at Rock Island State Park. Winding backroads transform every hill into a rewarding climb, offering a scenic ride and satisfying workout. After conquering the loop, you'll have plenty of time for the short hike to Twin Falls and to explore the park. (less)

Cycle through an ancient landscape at Pinson Mounds State Archeological Park. The park preserves more than 15 earthen mounds, some towering more than 70 feet high and dating back 2,000 years. This route offers enough climbing to provide a satisfying workout, without leaving you exhausted for a post-ride stroll through the park. (less)

This loop route begins and ends at Natchez Trace State Forest grocery store and encircles the preserved woodlands of nearby Natchez Trace State Park. These tree-covered roads are a rare treat in a largely agricultural region, offering cool shade during Tennessee's humid summer afternoons. The route explores some farmland roadways in the middle of the ride to balance out the scenery. There are several opportunities to venture off route to soak up the views at Pinoak, Red Bud and Cub Lake within the State Park. There are ample camping and lodging options within the park for those seeking a multi-day riding experience. (less)

Some of the best riding in East Tennessee can be found in the Sequatchie Valley. That's why you'll find not just one, but three routes, each offering a unique perspective on the valley's geography and charm. The Upper Sequatchie Valley Loop will take you from Pikeville north to where the Sequatchie Valley begins. Enjoy the valley’s undulating, low-traffic roadways and historic agricultural landscape, as well as gorgeous views of Walden's Ridge and the South Cumberland Plateau. Pair this route with the Middle and/or Lower Sequatchie Loops for a multi-day riding expedition. (less)

Some of the best riding in East Tennessee can be found in the Sequatchie Valley. That's why you'll find not just one, but three routes, each offering a unique perspective on the valley's geography and charm. The Lower Sequatchie Valley Loop begins in Jasper, Tenn., and heads north through the valley toward the community of Cartwright, featuring fantastic roads and gorgeous views of Walden's Ridge and the South Cumberland Plateau, with unique stops along the way. Pair this route with the Middle and/or Upper Sequatchie Loops for a multi-day riding expedition. (less)

The Chatata Valley Loop is a scenic ride featuring fun, twisty backroads through farmlands and excellent pavement - plus a fantastic winery with a panoramic view of the mountains of the Cherokee National Forest. Don't be fooled by this route's short length - this is hill country, and many of the punchy climbs on this route are in the double-digit grades. So be prepared to gear down and power up the steep pitches. It's a challenging route that feels much longer than 25 miles, but it is well worth the effort to take in the surrounding mountains and scenery. (less)

Bell Buckle is set within Middle Tennessee's iconic countryside and has that Small Town America appeal. This makes it a perfect place to launch a ride through the scenic landscape of South Central Tennessee, followed by rest and relax in the quaint town of Bell Buckle, Tenn. (less)

The Sewanee Loop route combines rolling roads through farmland with an exhilirating tree-covered descent and climb back up Tennessee's South Cumberland Plateau. This ride begins and ends at the historic University of the South campus in Sewanee, Tenn., which is surrounded by the wilds of South Cumberland State Park and Savage Gulf State Park. You’ll be hard-pressed to get more bang for your buck on any 33-mile route, especially surrounded by the spectacular landscape of Tennessee's South Cumberland region. (less)

This scenic loop winds through some of Middle Tennessee's wooded landscapes and a section of the Natchez Trace Parkway, a national roadway that commemorates and preserves the historic Nachez Trace, which connects Nashville, Tenn., to Natchez, Miss. This scenic route highlights the pastoral landscape of Tennessee, traversing the hills and waterways that make this area unforgettable. (less)

This loop route is big on Northwest Tennessee scenery from start to finish. The route begins in the heart of Troy, Tenn., and meanders through curvy, hilly terrain, open farmland, and tree-lined creekside strolls. This route delivers just enough climbing to give you a proper workout. (less)

This loop route begins and ends at the Tennessee National Wildlife Refuge along the Tennessee River, which was formed to preserve important habitat for migratory birds. The midway point of the route is Paris Landing State Park, one of the state's most-popular parks located along the western shore of the Tennessee River and Kentucky Lake Reservoir. Immerse yourself in the rolling terrain as you enjoy one of West Tennessee's most treasured landscapes. (less)

This out-and-back journey begins in downtown Camden, Tenn., and heads east to explore Nathan Bedford Forrest State Park, located along the banks of the Tennessee River and Kentucky Lake Reservoir. While there, make time to stop at the Tennessee River Folklife Interpretive Center and Musuem, situated on one of the highest points in West Tennessee, Pilot Knob. This route offers plenty of climbing and highlights the region's historic landscape. (less)

This rollercoaster of a ride takes you through an incredibly historic rural landscape, with a stunning backdrop of the Great Smoky Mountains. The route begins at David Crockett Birthplace State Park, known as the birthplace of legendary Tennessee frontiersman Davy Crockett, and features East Tennessee's typical rolling terrain. While the climbs may be short, their frequency adds a challenge paired with fun descents that offer cyclists a chance to settle into a rythym while exploring the area. The state park is situated along the Nolichucky River, offering river rentals, camping and interpretive exhibits - you can even purchase your own Davy Crockett-style raccoon hat! (less)

Brace yourself for this epic ride up Roan Mountain, which reaches an elevation of 6,285 feet at its highest point. This historic mountain landscape - which witnessed action during the American Revolution - is covered in native rhododendrons that bloom each June. The Appalachian Trail traverses the mountain - it's a short, steep hike up the AT to Carvers Gap (elevation 5,512 ft.) to view the sea of surrounding mountains. It's important to plan accordingly to tack this challenge - early mornings are best and avoid riding this route during events like the annual Rhododendron Festival. The Roan Montain Challenge is a big effort with a huge payoff - something you will never forget! (less)

This scenic out-and-back route begins in the charming town of Jonesborough - Tennessee's oldest town - and works its way to Horse Cove Gap within the mountains of the Cherokee National Forest. Enjoy the stunning mountain views as the route transitions from rural farmland to forested mountain roadways. After your ride, plan to explore Jonesborough's downtown, with its lovely display of buildings that range from the 18th to 21st century architectural styles, as well as numerous restaurant options, a distillery and quaint shops. (less)

The Farmland to Forest Challenge will test your endurance. While this route may not feature a signature climb, it’s classified as a Challenge because of the cumulative elevation gain and steep grades along the way. Prepare for the burn that will leave your legs trembling — but the reward? Spectacular views that make every pedal worth it. (less)

If you relish a challenging ride with incredible scenery, the Norris Lake Hill Challenge is one to experience. This route boasts steep climbs and challenging gravel sections, manageable with 30mm tires or greater. After conquering the climbs, cool off with a quick dip in Norris Lake. (less)

Few rides in the eastern U.S. offer climbs and descents of this length, coupled with vistas comparable to Colorado and the western states. The entire Foothills Parkway is a treat, but the new section is a rare gem that will undoubtedly be ranked as one of your top all-time favorite rides. The views of the Smoky Mountains are that good, and the descents are that fun! It’s a tough ride (even when shortened) with a huge payoff for the effort. We can’t recommend this ride enough. (less)

Meeman-Shelby Forest State Park is just 13 miles north of Memphis, but it feels like another world entirely. The park features mature Bald Cypress trees and Tupelo swamp, as well as a rollercoaster of roads that wind through the wooded landscape along the Mississippi River. Most of the park sits atop the Chickasaw Bluffs that rise up from the river bottomlands and are covered with large oak trees. Although the mileage and total elevation gain are relatively low, this route packs a punch with multiple short but very steep climbs, the majority of which have grades in the mid-teens. (less)

Seeking a route to stretch your legs without confronting major climbs? Look no further - the Covington Loop offers gentle rollers and predominantly flat farm roads, ideal for leisurely spinning or honing your time-trialing skills. Enjoy a hassle-free ride that's great for cyclists of all riding and endurance levels. (less)

Enjoy a delightful loop ride through miles of serene low-traffic farm roads, complete with just the right amount of twists and turns to keep things interesting. (less)

The Lascassas Loop offers stunning scenery and a challenging workout! There are ample opportunities to stretch your legs amidst wide-open spaces followed by some serious climbs that will test them. Enjoy consistently smooth pavement throughout most of the route. This route rolls through one of the state’s fastest growing counties, where you toe the line between rural Tennessee and suburbia, watching new houses pop up in former farm fields. Fortunately, there’s still plenty of unpopulated backroads to explore, and this route showcases them. (less)

Experience the charm of Tennessee's pastoral landscapes on this exceptional route, featuring a harmonious blend of open fields, wooded stretches, and serene creekside rambles. While the scenery delights, prepare for a workout with challenging climbs, including some with grades reaching the upper teens. This ride promises both visual splendor and physical exertion, making it an unforgettable adventure for cyclists seeking the best of Tennessee's countryside. (less)