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Learn more about Upper Cumberland Wine Trail.

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We invite you to follow the Upper Cumberland Wine Trail where you’re certain to find a Tennessee wine to suit every taste from West to East.  As you venture through the West trying some of the dry wines at Cellar 53, or when you further your knowledge at Red Barn where their owner’s understanding of grapes exceed expectation. After exploring the West, the center of our trail offers picturesque views at Del Monaco, and the small but cozy operations of Holly Ridge, while finishing up the central region by stopping at Northfield to indulge in the family atmosphere that dates back five generations of tending to the family farm.  Finally to the East where you can visit Highland Manor-Tennessee’s oldest winery, or excite your palate with Stonehaus’ sparkling wines, and don’t forget Chestnut Hill where you can tour the process of making wine and view their fermentation capacity of over 23,000 gallons—making it one of the largest wineries in the state of Tennessee.  As you travel the trail, pick up our card at any of the Upper Cumberland wineries or visitors centers.  Visit all our wineries and have this card stamped at each winery you visit.  You’ll receive a special thank you gift when you complete the trail and get your final stamp.  It matters not where you begin or where you end, good times abound all along the way! For more information on the trail, go to our website, or call toll—free at 1-800-868-7237. 

For further information, visit each of the wineries' individual pages on

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Map of Upper Cumberland Wine Trail
Vineyard Grapes
Wine Cellar
Exterior of Highland Manor Winery
Upper Cumberland Wine Trail

For the most up-to-date hours and information, please contact Upper Cumberland Wine Trail directly.


Cookeville, TN 38502


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Admission Rates



See the individual winery websites.

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