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Wine Trail


For more information on Agritourism in our Upper Cumberland Counties...


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Wine Trails
in the Upper Cumberland Region



Wine Trail Map

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What better way to see and experience the Upper Cumberland Region! Whether you're coming from Nashville, Knoxville, or points in between, there's a Winery close to you. Plan ahead and spend some time enjoying the best tasting wines produced in Tennessee. 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

»Click on the Winery below for more information!«

~ Chestnut Hill Winery ~
Chestnut Hill WineryChestnut Hill WinerySituated on the beautiful Cumberland Plateau, 2000' feet above sea level, the “Chestnut Hill Winery” is a "Place to Taste". The winery has a fermentation capacity of over 20,000 gallons, making it one of the largest wineries in the state of Tennessee.  Fermentation is done in stainless steel tanks and all wines produced are bottled on the premises. 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. Stop in and try their new wines. Released in 2009 Chestnut Hill Winery is proud to introduce 3 new wines, "MANDOLIN BLANC" a dry white wine with a hint of oak, "DULCIMER WHITE" a semi dry wine and their "SWEET WHITE MUSCADINE". Chestnut Hill Winery; "A PLACE TO TASTE BEFORE YOU BUY".

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78 Chestnut Hill Road
Crossville, TN 38555
Phone: 931-707-7878
Website: www.chestnuthillwinery.com
~ DelMonaco Winery & Vineyard ~
DelMonaco WineryWe make a variety of wines and grown 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. Opening Hrs.: Mon. – Sat. 10am – 7pm Sun. 12pm-5pm.

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600 Lance Drive
Baxter, TN 38544
Phone: 931-858-1177
Fax: 931-858-1178
Website: www.delmonacowinery.com
E-Mail: barbara@delmonacowinery.com
~ Highland Manor Winery ~
Highland Manor WIneryThe English Tudor building and classic cellar are evidence that tradition runs deep at Highland Manor. 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. Known for our famous Muscadine wine and our Old World charm. Free tastings and tours (time permitting)2965 South York Highway
Highway 127
Jamestown, TN 38556
Phone: (931) 879-9519
Website: www.highlandmanorwinery.net
E-Mail: HMW@twlakes.net


~ Holly Ridge Winery & Vineyards ~
Holly Ridge WineryHolly Ridge Winery is a family-owned and -operated farm winery located in Livingston, Tennessee.

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.

Watch our Video486 O’Neal Road
Livingston, TN 38570-5109
Phone: (931) 823-8375
Website: www.HollyRidgeWinery.com
E-mail: hollyrdgwine@twlakes.net

~ Red Barn Winery & Vineyards ~
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.

Watch our Video 1805 Tanyard Road
Lafayette, TN 37083
Phone: 615-688-6012
Fax: 615-688-6015
Website: http://www.redbarnwinery.com
E-mail: clements@nctc.com
~ Stonehaus Winery ~
Stonehaus WineryStonehaus Winery is located high atop Tennessee’s Cumberland Plateau. Located just off Interstate 40 at Exit 320. Stonehaus Winery is open to visitors 7 days a week year-round. Taste our fine wines from the rich Merlot to the dry Pinot Gris to our famous Muscadine. After the wine tour stop at our gift shop, for gourmet foods, antique mall, and more. on premises.

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


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