We invite you to discover the seven wineries along the Upper Cumberland Wine Trail. We are certain you will find a Tennessee wine to suit your taste. As you travel the trail, pick up our card and have it stamped at each winery you visit. You’ll receive a special thank you gift when you complete the trail.

· It matters not where you begin or end the trail good times abound all along the way!
· Plan your own route and take your own time, experience the Upper Cumberland!
· Read the blog "Drink Up the Good Life in Tennessee Wine Country" featured on tnvacation.com


Winery Map

»Click on the Winery below for more information!«

~ Chestnut Hill Winery - 7
Chestnut Hill WinerySituated on the beautiful Cumberland Plateau, 2000' feet above sea level, the "Chestnut Hill Winery" is "The Place to Taste". The winery has a fermentation capacity of over 23,000 gallons, making it one of the largest wineries in the state of Tennessee. Fermentation takes place in stainless steel tanks and all wines produced are bottled on the premises. While visiting ask for a tour of the winery. We want your visit to be enjoyable, memorable, and educational. The best and most enjoyable way to shop for wine is to visit the winery in person. When you visit the Chestnut Hill Winery, be sure to have a taste of the wines. Stroll through the unique gift shop with mostly Tennessee made items. Chestnut Hill Winery also has "Gifts to Go"; these gifts are wrapped and ready, waiting for you to pick up.

HOURS~ Mon-Sat: 9am-6pm; Sun: 12pm-5pm
Major holidays: Closed

78 Chestnut Hill Road
Crossville, TN 38555
Phone: 931-707-7878
GPS Coordinates: 35.9608, -84.9829
Website: www.chestnuthillwinery.com

~ DelMonaco Winery & Vineyard - 1
DelMonaco WineryAt DelMonaco Winery we make a variety of wines and grow our own grapes on site. We produce whites, reds and dessert style wines that will please a range of palates. Free tastings of all of our wines and winery tours available daily. Our beautiful Tuscan style building has a two story ball room with wrap-around balcony overlooking the vineyards. Our rooms are available for rent for weddings, private parties, business meetings, or any occasion. Back patio and picnic area in the vineyard available for guests to enjoy wine and cheese outdoors.

HOURS~ Mon–Sat: 10am–7pm; Sun: 12pm-5pm
Major holidays: Closed

600 Lance Drive
Baxter, TN 38544
Phone: 931-858-1177
GPS Coordinates: 36.16335, -85.61555
Website: delmonacowinery.com
E-Mail: barbara@delmonacowinery.com
~ Highland Manor Winery - 5
Highland Manor WIneryThe English Tudor building and classic cellar are evidence that tradition runs deep at Highland Manor off TN 127 near Jamestown. While traditions are important, it is also important to recognize progress in the wine making equipment. Tennessee's oldest licensed winery specializing in handcrafted wines. Highland Manor is known for their famous Muscadine wine and our Old World charm.
Free tastings and tours(time permitting).

HOURS~ Mon-Sat: 9am-5pm; Sun: 11am-5pm
Call for Holiday Hours

Highway 127
Jamestown, TN 38556
Phone: (931) 879-9519
GPS Coordinates: 36.37741, -84.9429
Website: www.highlandmanorwinery.net
E-Mail: HMW@twlakes.net

~ Holly Ridge Winery & Vineyards - 3
Holly Ridge WineryHolly Ridge Winery is a family-owned and -operated farm winery located in Livingston, off TN 85. Since 1998, Holly Ridge Winery has been producing award-winning wines made from grapes grown in sloping vineyards surrounding the winery. Much emphasis is placed on viticulture at the winery as we want to use only the highest quality grapes for our wines. Currently, we grow 14 different cultivars ranging from the French hybrid variety Seyval Blanc to American standards such as Concord and Niagara.

HOURS~ Mon-Sat: 10am-6pm; Sun: Closed

486 O’Neal Road
Livingston, TN 38570-5109
Phone: (931) 823-8375
GPS Coordinates: 36.37419, -85.38557
Website: www.HollyRidgeWinery.com
E-mail: hollyrdgwine@twlakes.net

~ Northfield Vineyards - 4
Holly Ridge WineryNorthfield Vineyards is located on the Ray Family Farm that goes back five generations. The barn that was built in 1904 still stands as a reminder of the days when folks who lived in rural areas lived off the provisions of the farm. The Ray Family Farm tended to milk cows, crops, and tobacco. Today, it's the home of Northfield Vineyards. It's Southern Hospitality at its best at Northfield Vineyards. The country setting with beautiful views is worth the visit all by itself. When you add the friendliness of the Ray Family, you will be glad you came.

Hours~ Fri-Sat: 10am-5pm; Sun: 1-5pm

515 Ray Cemetery Rd.
Sparta, TN 38570-5109
Phone: (931) 761-9463
GPS Coordinates: 36.0481303, -85.5254971
Website: www.northfieldvineyards.com

~ Red Barn Winery & Vineyards - 2
DelMonaco WineryThe Red Barn Winery & Vineyards is located on the Highland Rim of Macon County …sitting between Lafayette and the historic Red Boiling Springs.  We are located approximately 50 miles northeast of Nashville. The scenic Red Barn Winery & Vineyards is the first in Macon County to become an Agricultural Farm Winery.  Over this 100-acre farm lie the North American and the French Hybrid grapes of the Glen Clements family.

HOURS~ Wed-Sat: 11am-5pm; Sun 1-5pm
Mon, Tue & all major holidays: Closed

1805 Tanyard Road
Lafayette, TN 37083
Phone: 615-688-6012
GPS Coordinates: 36.491570, -85.942590
Website: redbarnwinery.com
E-mail: clements@nctc.com
~ Stonehaus Winery - 6
Stonehaus WineryStonehaus Winery a family owned winery located high atop Tennessee’s Cumberland Plateau produces a generous variety of wines from the dryer sparkling Seval Blanc to the sweeter and much beloved Muscadine, otherwise known as “God’s gift to the sunny south”. Additionally, we have homemade fudge, gourmet foods, unique gifts, and educational toys.

HOURS~ Mon-Sat: 9am-7pm; Sun: 12pm-5pm
Major holidays: Closed

2444 Genesis Road
Crossville, TN 38558
Phone: (931) 484- WINE (9463)
GPS Coordinates: 35.98503, -85.01110
Website: www.stonehauswinery.com


Wine, Stien, and Shine Tour