Upcoming Wine Trail Events



Chocolate Lovers' Wine Trail logo

Chocolate Lovers' Wine Trail

Travel the trail to enjoy delectable treats. Each paired with a special Tennessee Wine

From February 13 to 16, 2020

Thursday, Friday, & Saturday: 10am to 6pm
Sunday: Noon to 5pm

Tickets: $30 Per Person • $50 Per Couple • Advance Purchase Required

Ticket price includes a souvenir wine glass

Transportation to each of the wineries is not included in the ticket price.

*If you want to leave the driving to others please visit:
Tour the UC logo

Event will be held regardless of weather. No Refunds

You must be at least 21+ years of age to participate in the Upper Cumberland Wine Trail events.

Visit any or all of the participating wineries and enter your ticket in a drawing for:

One gift certificate for a two night stay at Talley's Cabins & Breakfast. And one gift certificate for a basket with goodies from each of the participating wineries.


Cellar 53 • Brush Creek

Salted Dark Decedant Chocolate Tart with Old Vine Zinfandel
115 Oakview Drive East • 615-934-3353

Chestnut Hill • Crossville

Whipped Peanut Butter Mousse with Fiddler Red
78 Chestnut Hill Road • 931-707-7878

DeMonaco • Baxter

Double Chocolate Chip Cookie with Razzmatazz Raspberry
600 Lance Drive • 931-858-1177

Highland Manor • Jamestown

Fresh Strawberry and Cream Cupcake with Royal Rosé
Highway 127 • 931-879-9519

Holly Ridge • Livingston

Rich Chocolate Brownie Bits with Sweet Ruby Red
489 O'Neal Road • 931-823-8375

Northfield • Sparta

Delectable Cream Cheese or Chocolate Tartlet with Ruben's Red, Red Cranberry or Shag Nasty Red Moscato
515 Ray Cemetery Road • 931-761-9463

Paris • Cookeville

Cotton Candy French Meringue Nests with Cotton Candy Wine
701 E. Spring Street • 931-646-0897

Stonehaus • Crossville

Lusciuos Red Wine Spiked Brownies with Kiss this Cherry Wine
2444 Genesis Road • 931-484-9463


How the Trail Works

1. Start the event at any of the eight participating wineries.
Please note - each winery's tasting room policies remain in effect during Wine Trail events and are not included in the ticket price. Some wineries charge for additional wine tasting.

2. Pick up your souvenir wine glass at the first winery you visit.

3. Visit the wineries in any order you wish.

4. Take your ticket and wine glass with you to each stop.

5. Drop off your ticket at the last winery you visit to enter the drawing

6. Have fun, but please enjoy this event responsibly

Winery Map