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.
View our image gallery
2nd Annual Wine Festival
Join us for Art – Jazz – Food
At the Watertown Wine Festival
June 3rd, 2017... Visit our Events page for more details.
Follow us on Facebook for the latest in Events & Specials at all 8 Upper Cumberland Wineries