Crossville & the Upper Cumberland
Wineries & Wine Country
Explore nearby wineries for a tasting, a vineyard visit, or an afternoon outing. Start with the current Crossville updates below, then plan a trip to Baxter or Jamestown.
Crossville winery updates
Chestnut Hill Winery
Permanently closed
Chestnut Hill’s official website announces its permanent closure. The former Crossville location is no longer listed here as a tasting destination.
Read the winery’s closure notice →Stonehaus Winery
No public tasting room or tours
Stonehaus continues making and distributing wine, but no longer operates a public storefront or offers tours, tastings, or on-site events. Its production location is now in Smithville.
Wineries to visit in the region
These wineries are outside Crossville. Use the directions links to plan your route.
Baxter, Tennessee
DelMonaco Winery & Vineyards
Explore the vineyard, tasting experiences, bistro, and winery events. Check the official website for visit options and reservations.
600 Lance Drive
Baxter, TN
931-858-1177Jamestown, Tennessee
Highland Manor Winery
Visit for wine tastings, guided tours, and a gift shop. The winery asks groups of more than ten to call ahead.
2965 South York Highway
Jamestown, TN
931-879-9463
Plan an outing
Hours & reservations
Check directly with the winery for today’s hours, tasting options, tour availability, and group arrangements.
Events at DelMonaco
Browse the winery’s calendar for upcoming activities and ticket information.
View winery events →Find more regional wineries
The Upper Cumberland Wine Trail offers a regional directory. Confirm each stop with its own website before traveling; some directory listings may be older.
Explore the wine trail →Make a day of it
Find restaurants, places to stay, and local attractions. Our maps page can help you explore the area.
Winery details reviewed October 4, 2026 using the businesses’ official websites. Follow the links above for current information.