Upcoming Wine Trail Events


Saturday, September 8, 2018
11am ~ 5pm at the Highland Manor Winery
2965 South York Highway, Jamestown, TN

Tickets: $15 in advance and may be purchased on line or at any of the participating Wineries.
*Event will be held regardless of weather. No refunds. You must be at least 21 years of age to participate in Wine Trail events.



UCWT LogoJuly 28th ~ Upper Cumberland Cajun Day at Highland Manor in Jamestown


UCWT LogoAug. 18th ~ Dog Days of Summer Music
Join us for our first music event in the new pavilion! We’ll have Just Jeff playing from 4 to 6 p.m. and The Connection Band playing from 6:30 to 10:30 p.m. Templeton BBQ will be smoking up some delicious goodness and Happy Trails Brewery will be serving up the newest local craft beer here for a night of fun during the dog days of summer! Admission $5/each and no outside alcohol allowed!


DelMonaco logoSept. 22nd ~ Cork & Pork Festival
What could be better than Wine, Music & “Finger Licking Good" Barbecue? The Cork & Pork Festival is a celebration of America’s biggest pastime showcasing Cookeville’s best BBQ cooking, fine wine, live music, and craft vendors from across the state. Cookeville’s top BBQ restaurants and local teams will serve up their specialties while competing for the People’s Choice Award traveling trophy and of course bragging rights!
Entrance fee: $3 Cash for General Admission. Click HERE for more info

UCWT LogoSept. 28th-30th ~ Fall Market at Northfield Winery in Sparta. Over 50 vendors & great food!


UCWT LogoOct. 13th ~ Blues & Boooos & Local Brews
Join us for a night of Blues music with Few Miles On band, a costume contest and local brews and Northfield wine! More details to come!

Celler 53 logoOct. 13th ~ 4th Annual Harvest Festival. Live Music starts at 1pm. Food Trucks, Shopping & Great Wine!

DelMonaco logoOct. 20th ~ Wine Train from Nashville to DelMonaco Winery & Vineyards in Baxter


UCWT LogoNov. 3rd ~ Art N Ale Trail  at Northfield Winery in Sparta


DelMonaco logoNov. 10th ~ Wine Train from Nashville to DelMonaco Winery & Vineyards in Baxter