Top Places To Design Your Own Two-Wheeled Wine Tasting Trip

What if organized tours aren’t your thing? If you’d rather set your own course and agenda, there are plenty of options for areas and trails that are cyclist-friendly, scenic and surrounded by wineries. Here are three ideas we love:

Virginia Capital Trail: This dedicated, paved pedestrian and bicycle trail connects Jamestown and Richmond for 52 miles along the scenic Route 5 corridor. Cyclists can stop for sips at Upper Shirley Vineyards, located near mile marker 30, and end at Williamsburg Winery, which is about 5 miles past the end of the trail, accessible either via Jamestown Road or the Colonial Parkway (with scenic views of the water).

Middleburg: An area of wineries called Mosby Cluster—primarily along Route 50, John Mosby Highway, as it travels through the villages of Aldie and Middleburg—sit close enough together that you could easily bike from one to the next. We recommend getting off your cycle to swirl at Chrysalis Vineyards, Green Hill Winery & Vineyard and Boxwood Estate Winery, all a short distance from each other.

Virginia Creeper Trail:
Take a recreational ride on this 34-mile scenic trail in the state’s southwestern corner that goes from Abingdon through the town of Damascus along the Whitetop Laurel River and up to its highest point at Whitetop Station near the N.C. State Line. Plan on a visit to Abingdon Vineyard—from the Abingdon trailhead, it’s about 8.5 miles to Alvarado Station, where you can take a detour off the trail to the winery, about a half mile away on Alvarado Road.

Written By

Melissa Stewart