Upper Cumberland Wine Trail

Upper Cumberland Wine Trail

A road trip through Tennessee wine country.

Add to TripRemove

From rustic tasting rooms to picture-perfect rows of grapevines curving up rolling hillsides, discover the rural charm of wine country in middle Tennessee’s Upper Cumberland region. As you drive down quiet country roads to each vineyard on the Upper Cumberland Wine Trail, take in picturesque views of verdant valleys, glittering lakes and charming small towns along the way.

Vineyards at Cellar 53 Winery in Brush Creek
Vineyards at Cellar 53 Winery in Brush Creek

Start your Tennessee wine experience at Red Barn Winery & Vineyards in Lafayette, offering an array of sweet wines and scenic vineyard views less than an hour south, the Cumberland River snakes through forested mountains, and it’s here you’ll find Cordell Hull Lake: an outdoor oasis with waterfront cabins, fishing and boating. Also on the Cumberland River, the historic riverboat town of Granville offers all the charm of a bygone era. Stop in the old-fashioned T.B. Sutton General Store for lunch and an iced sweet tea, and don’t miss the Old Time Music Hour at the store with Southern cookin’ and live music.

wine train
Take the Wine Train from Nashville to the Upper Cumberland 

Situated on a family farm in Brush Creek, Cellar 53 Winery produces approximately 10 wines made from locally grown fruits. After a wine tasting and tour, enjoy the natural beauty of nearby Center Hill Lake at Edgar Evins State Park, where you can enjoy hiking, boating and fishing. Or enjoy a paddle down the Caney Fork River in a scenic canoe trip with Canoe the Caney or a kayak tour with Caney Fork Outdoors.

Visit Cream City at Cookeville’s West Side for Ice Cream
Visit Cream City at Cookeville’s West Side for Ice Cream

At DelMonaco Winery & Vineyards in Baxter, enjoy wine tastings in the grand Tuscan-style tasting room, and head out on the wraparound balcony to enjoy sweeping views of the vineyard. For a family-owned winery in the heart of pastoral Sparta, visit Northfield Vineyards, located on the historic Ray Family Farm, where you can sample an array of unique varietals and stock up on locally made fruit butters, preserves, cheeses, homemade soaps and more.

A little moonshine from Short Mountain Distillery, anyone? 

Farther south, marvel at incredible rock formations or catch a Bluegrass Underground concert inside the cave of McMinnville’s Cumberland Caverns, or relax with a guided meditation or yoga class at the Isha Institute of Inner-Sciences. In Spencer, explore miles of rugged hiking trails atop the Cumberland Plateau at Fall Creek Falls State Park.

Up north, Holly Ridge Winery and Vineyard in Livingston offers everything from dry red wines to sweet white wines. Buy a bottle, and make your way to Dale Hollow Lake, where you can stay in a waterfront cabin or quaint bed-and-breakfast and enjoy smallmouth bass fishing, houseboating or just picnicking on the shores.

Dale Hollow Lake
Dale Hollow Lake - #4 best houseboat lake in the country

At Big South Fork National River & Recreation Area, go hiking or horseback riding during the day and stargazing at night. Nearby is Highland Manor Winery, Tennessee’s oldest winery. Drive along the scenic, rural roads to this English Tudor-style winery just outside downtown Jamestown, where you can enjoy free tours and wine tastings.

twin falls
Twin Falls at Rock Island - perfect for kayaking 

Meanwhile, in Crossville, learn about the winemaking process with a tour and tasting at Chestnut Hill Winery, or stop by Stonehaus Winery for wine tasting, custom cheese pairings and live music events. During the day, delve into local history at Cumberland Homesteads Tower & House Museum, and at night, experience the magic of the theater with enchanting musicals, rollicking comedies and more at one of the most popular regional theaters in America — Cumberland County Playhouse. Crossville also happens to be the “Golf Capital of Tennessee,” boasting 10 championship courses in the area. For the ultimate retreat, stay at nearby Fairfield Glade, a stay-and-play resort with five championship courses, nature trails and serene lakes.

Rob Ramsey
Wine tasting with Rob Ramsey at Stonehaus Winery in Crossville

Get even more ideas for your perfect road trip through scenic Upper Cumberland

Ole Time Music Hour at Sutton General Store in Granville
Ole Time Music Hour at Sutton General Store in Granville

Take a look at our Upper Cumberland Visitor's Guide

Map with directions to the 8 Upper Cumberland Wineries
Map with directions to the 8 Upper Cumberland Wineries 


Places in this article

The Mountains Are Calling You to Gatlinburg

The mountains are calling.

Read More