Upper Cumberland Wine Trail

Discover the Upper Cumberland Wine Trail


Explore the nine 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, Paris Winery in Cookeville, 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!

Wineries on the Trail


Chestnut Hill Winery


Located in Crossville ,TN, the golf capital of TN atop the beautiful Cumberland Plateau. Chestnut Hill Winery has capacity of over 20,000 gallons, making it one of the largest wineries in the state of Tennessee. Fermentation takes place in stainless steel tanks and all wines are bottled onsite.

DelMonaco Winery


It all starts with the vine. Take a waling tour of our 20+ acres of manicured vineyard and enjoy a free tasting of our award winning wines fermented on the premises of the Tuscany style winery.

Highland Manor Winery


For over three decades, Highland Manor Winery has been producing fine, handcrafted wines in Jamestown, TN. Our owners, Frederick and Rhonda Moody, are committed to continuing the winemaking tradition in Tennessee.

Holly Ridge Winery


Here at Holly Ridge Winery, we focus on the production of fine wines using Eastern wine grapes. We now offer a selection of over 29 wines, ranging from dry dinner wines to sweet dessert wines. It is our goal to have a wine to please every palate!

Northfield Vineyards


Northfield Vineyard and Winery is a family-owned winery tucked back in the hills of White County, Tennessee. The farm on which the winery and vineyard sit has been in the Ray family since 1904. The farm proudly grows not only grapes but hosts the stars of Northfield Vineyards, Burt and Rube.

Paris Winery


The farm was originally a cornfield with not even as much as a dirt road. Filling their land with cattle, pigs, ducks, geese, rabbits and domestic animals, they decided to plant a few acres of grapevines to make some personal wine. The vineyard started with 5500 vines and today there is over 9000 vines comprised of 23 types of grapes. About 3 years later, they decided to open the winery.

Stonehaus Winery


Stonehaus Winery enjoys statewide and multi-state distribution. Stonehaus wines can be found at the winery, in liquor stores, and grocery stores in Memphis, Nashville, Chattanooga, Knoxville, Tri-Cities, and all points in between. We are very proud or our wines, heritage, and family we have created here in the beautiful Cumberland Plateau.


Wine Trails