Alvin C. York Tour
From Clarkrange to Cookeville
Approximately 104 miles roundtrip
Cumberland Mountain General StoreStart this historic hero journey by exiting I-40 at Exit #317. Go North on Hwy. 127 towards Jamestown. In Clarkrange, be sure to stop by the Cumberland Mountain General Store for the best milkshake on the plateau. Continue on Hwy. 127 N for approximately 18 miles from the store. Turn left to go towards the on the Hwy. 127 Jamestown Business District route. Go through town, past the courthouse and Mark Twain Park. On the other side of Jamestown, you’ll see Alvin C. York Agricultural Institute, founded by World War I hero, Sgt. Alvin C. York. Continue on through the Pine Haven Community. At the 127 By-Pass intersection, turn left to continue north on Hwy. 127. Turn left onto Squirrel Flat Road. Take another left on Double Top Road. Wind your way to the first fork, where you will bear left. At the second split, veer left again. Slow down to enjoy the views as you descend this majestic ridge. Continue straight until the road T-bones with Hwy. 325 (also called Stepp Gap Road). Turn right onto Hwy. 325 and follow until it intersects with Hwy. 127 South. Turn right onto Hwy. 127 S and get the camera ready for the Valley of the Three Forks.
This route will take you past old-fashioned general stores and through the heart of Sgt. York’s old stomping grounds. Stretch you legs at the state historic park named in his honor. Here you can take a guided tour of Sgt. York’s homeplace, visit the gristmill, or walk over the swinging bridge. Grab a cold drink and a sandwich while you sit on the banks of Wolf River and soak up Spring in the valley. When you’re ready, take Hwy. 127 S back into Jamestown.
At the top of the mountain, remember to turn right off the by-pass to go through town. At the second red light, turn right to go west on Hwy. 52: a can’t miss section of the tour. This road winds down through West Fentress. While it’s curvy, it offers spectacular views of the valleys and mountains. Enjoy the rich colors as you finish the journey by following Hwy. 52 through the town of Livingston to Hwy. 111. Go south on Hwy. 111 towards Cookeville and I-40. (Roughly 104 miles roundtrip.)
Beautiful Barns/Historic Hotels Route
From Gainesboro to Red Boiling Springs
Approximately 120 miles roundtrip
Start this rural route by exiting Interstate 40 at Exit #280. Go north on Hwy. 56 towards Gainesboro. Just on the other side of Gainesboro, turn left to stay on Hwy. 56N and cross over the beautiful Cumberland River. As you travel through the rich bottom land farms, start counting the stately old barns scattered throughout the countryside. Stay on 56 as you begin the curvy climb out of the valley, through the tunnels of trees. Veer right at the intersection to go west on Hwy 262. At the stop sign, go straight to stay on 262 (also Union Camp Road). Continue on Union Camp Road until it ends at the stop sign. Turn left onto Red Boiling Springs Road. Travel approximately 1.4 miles and turn left onto Ferguson Hill Road. Roll the windows down and enjoy the rural solitude as you meander by the creek and drive under the canopy of big hardwoods. Watch for the wild turkeys!
At the end of Ferguson Hill Road, turn left on to Hwy 10 and then take the first road on the right; Ford Branch Road. Your barn count should be up in the double digits by now as you drive through more scenic farmland. Veer right onto Drury Ridge Road and slow down as you enter this “can’t miss” section. The road is narrow but the view from atop this ridge is breathtaking. You can see miles of hardwoods as you look down onto the valleys and hills of Macon County. Turn right at the stop sign and right again at the red light to put you on Hwy. 52 East.
Grab a snack in Lafayette and continue east on Hwy. 52, over Long Fork Creek and past the Nestle Bottling Plant. Turn left onto Hwy. 56 N at the historic hotel sign. In less than a mile, turn right at the Citgo onto Hwy. 151 East. Stop in and tour the trio of historic hotels and learn about Red Boiling Springs fascinating history as a popular health resort town back in the late 1800’s and early 1900’s. Don’t miss the motorcycle museum! Armour’s Red Boiling Springs Hotel, The Donoho Hotel, and The Thomas House all have wonderful stories to tell and comfy beds if the drive has you worn out. You can relax in a front-porch rocker or stroll through the grand trees along the creek before heading continuing east on Hwy 151.
Stay on Hwy. 151 as it winds you through more tree-lined farmland. Be sure to snap a few pictures of the weathered grey and red barns that line the way back to Hwy. 56. From there, take Hwy. 56 South back through Gainesboro and to I-40. (Roughly 120 miles roundtrip.)
• Exit Interstate I-40 at Exit #280 onto Highway 56N towards Gainesboro.
• Continue straight on 56N through Gainesboro.
• Turn left to stay on Hwy. 56N towards Red Boiling Springs.
• Continue on Hwy. 56N to Hwy. 262.
• Veer right at the intersection to go west on Hwy 262.
• Continue straight on Hwy. 262 (Union Camp Road) until it ends at Red Boiling Springs Rd.
• Turn Left onto Red Boiling Springs Rd.
• Turn Left onto Ferguson Hill Road.
• Turn left at stop sign onto Hwy. 10.
• Travel about 1000 feet and turn right Ford Branch Road.
• Veer right onto Drury Ridge Rd.
• Turn right at stop sign.
• At the red light, turn right to travel E on Hwy 52.
• Straight on 52E for about 13 miles.
• Turn Left onto Hwy. 56 N.
• Right onto Hwy 151 East.
• Straight on 151, to stop sign.
• Left on Hwy. 56 back towards Whitleyville, Gainesboro, then I-40.
Biker's Delight
Ongoing riding tours throughout the Upper Cumberland whether you're on your bike or in your car!
Listed below are links to some of the best rides the Upper Cumberland Region has to offer. Whether you're on your bike or in your car, these are well worth the drive. Each tour includes driving directions, estimated drive time, mileage, and points of interest. Discover some of the best scenic views, historical sites, eateries and more... just around the next bend.
Select anyone of the self-guided tours below for more information!
Center Hill Thrill - 77.8 miles (about 2h 15min)*
Ride Back In Time - 109.2 miles (about 2h 42min)*
Byway To Bluegrass - 104.6 miles (about 2h 38min)*
Sergeant Yorks Ride - 114.6 miles (about 2h 33min)*
Rugby Ride - 178.6 miles (about 4h 21min)*
Standing Stone Loop - 93.5 miles (about 2h 31min)*
Famous Falls - 177.9 miles (about 4h 31min)*
Over The Lakes - 148.8 miles (about 3h 56min)*
Water To Wine - 160.0 miles (about 3h 47min)*
Calfkiller Loop - 66.5 miles (about 1h 46min)*
Boilermaker - 120.1 miles (about 6h 6min)*
That Dam Ride - 183.8 miles (about 4h 48min)*
*The above tours were created and made possible through the "Harley-Davidson Ride Planner, Powered by H.O.G."
Broadway of America Tour
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Center Hill Lake Tour
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Hilltop heritage Tour
Begin this adventure by exiting I-40 at Exit #258. Go south on Highway 53 and turn left at the caution light. Check out the beautiful architecture of the older homes lining Main Street as you cruise through Gordonsville. At the railroad tracks, turn left to stay on Hwy. 264 N. Enjoy the roller coaster, as breathtaking views great you at the crest of each hill. Turn left onto Hwy. 70N. The rolling farmland continues as you drive by the Smith County residence of former Vice President Al Gore. Slow down to enjoy the ride on the green bridge that takes you over the Caney Fork River. Continue on down 70, past the interchange with Hwy. 25 and through the town of South Carthage. Turn right to go on the Cordell Hull Bridge, which was built in 1936, and over the Cumberland River.
Smith County CourthouseTurn left at the red light and welcome yourself to a picture of rural American life on the Smith County Courthouse Square. The courthouse was built in 1879, and in it’s time, was the finest in all of Tennessee. Hang a right onto Third Street to visit the Smith County Heritage Museum (open Wednesday, Friday, and Saturday from 10am to 2pm). The museum tells many stories and their new Civil War Exhibit is a must-see. Back on Main Street, continue going north, away from the courthouse. Enjoy the magnificent maple and magnolia trees that line the street. Continue until the intersection of Main and Hwy. 25. Go straight through the light, to travel on Hwy. 263 N, towards Cordell Hull Lake Dam. As you climb, enjoy the views of fall’s splendor on the left. Turn right at the sign for the U.S. Army Corp of Engineers Cordell Hull Lake Dam. Here you can enjoy a picnic and playground, hike on the Turkey Creek Trail, and stop by the visitor’s center. Be sure to go all the way to the end of the road to get a good look at the dam.
After you’ve gotten in touch with nature, backtrack back down to the red light. Turn left to go south on Hwy. 25. Smith County hands you a few more vistas of rambling farms and rolling hills as you follow the signs back to I-40. (Roughly 25 miles roundtrip.) If you’re tired of the interstate, go west on Hwy. 70 N to Lebanon or east to Cookeville.
- Exit I-40 on the Gordonsville Exit #258. Go south on Hwy. 53.
- Left at caution light to Hwy. 264 North.
- Left at RR crossing to stay on 264 N.
- Turn left to go west on Hwy. 70 North.
- Stay on Hwy. 70N through South Carthage.
- Turn right to go over Cordell Hull Bridge over Cumberland River and into downtown Carthage.
- Turn left at light.
- Continue down South Main Street.
- At intersection of Hwy. 25 and Main, go straight through light onto Hwy. 263N.
- Veer right at split.
- Right at Cordell Hull Dam sign.
- Return back to intersection of Hwy. 25 and 263.
- Left at light to go south on Hwy. 25 By-pass and back to I-40.
Wine Tour
Travel Tennessee's beautiful Upper Cumberland back roads, enjoying spectacular views, visiting small historic towns, and finding our wineries as you meander through our region.
Explore the eight Wineries & Vineyards that the Upper Cumberland Wine Trail has to offer. Cellar 53 in Brush Creek, Chestnut Hill in Crossville, DelMonaco in Baxter, Highland Manor in Jamestown, Holly Ridge in Livingston, Northfield in Sparta, Red Barn in Lafayette, Stonehaus in Crossville; all our wineries are small and family owned.
Follow the Upper Cumberland Wine Trail for a day tour or start planning your weekend of wine tasting. Pick up our Wine Trail Rack Card at any of the eight wineries or visitors centers and have card stamped at each winery you visit.
Once you have completed the trail and get your final stamp you'll receive a special thank you gift. It matters not where you begin or where you end, good times abound all along the way!
Join us for our very special events throughout the year. We host these events together as a trail as well as special tastings, music and more at our individual wineries.