Highland Manor Winery

Tennessee’s Oldest Winery — Right Here in Jamestown

Most people don’t expect to find an award-winning winery in the middle of the Cumberland Plateau. But then again, most people don’t know Fentress County like we do. Highland Manor Winery in Jamestown has been producing fine wines for over four decades, making it the oldest licensed winery in the state of Tennessee — and it’s been delighting visitors and locals alike ever since.

The Wines

Highland Manor produces a wide range of wines from both locally grown and regional grapes, with varietals including Chardonnay, Riesling, Cabernet Sauvignon, and a popular selection of sweet fruit wines that reflect the agricultural character of the region. The winery has earned numerous awards at state and regional competitions over the years, and the quality shows in every glass.

The Visit

A visit to Highland Manor is a genuinely pleasant experience. Free wine tastings are offered to all visitors of legal drinking age, and the staff is friendly, knowledgeable, and happy to walk you through the tasting selection. Guided tours of the winery and facilities are available, giving visitors a behind-the-scenes look at the winemaking process from grape to bottle.

The winery also has a well-stocked gift shop featuring wines, local cheeses, crackers, and specialty food items — making it an excellent stop for picking up gifts to bring home. Many visitors combine their winery visit with a picnic on the grounds, enjoying a glass of wine while taking in the peaceful Tennessee scenery.

The Perfect Ending to a Day Outside

After a day of hiking waterfalls, exploring Big South Fork, or touring the Alvin York historic park, there is no better way to wind down than with a tasting at Highland Manor. It has become a beloved Fentress County tradition for both locals and visitors — and one that keeps people coming back.