WOODSTOCK, VA — Wine enthusiasts and scenic drive lovers have a new reason to explore the rolling hills of Shenandoah County this fall. The Shenandoah Scenic Wine Loop offers visitors a picturesque journey through some of the region’s most charming vineyards, combining award-winning wines with breathtaking rural landscapes.
The self-guided tour begins in historic Woodstock and winds through the countryside, connecting four distinctive wineries along a carefully mapped route that showcases the best of Virginia wine country.
Starting southbound on Route 42, the loop first leads to Wolf Gap Vineyards via a series of country roads including Cave Ridge and Hamburg roads. From there, visitors can explore Cave Ridge Vineyards before continuing to the Winery at Kindred Pointe in Mount Jackson, where amenities include picnic areas, walking trails, and lawn games perfect for an afternoon of relaxation.
The journey concludes at Shenandoah Vineyards in Edinburg, the oldest vineyard in Shenandoah County, before looping back north to Woodstock along Ox Road.

“This route really captures the essence of our agricultural heritage while celebrating our growing wine industry,” said one local tourism official.
The scenic loop is ideal for a day trip and offers visitors a chance to sample Virginia wines while taking in the pastoral beauty of the Shenandoah Valley.
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