VIRGINIA: Wine Country Itinerary

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Below is a brief description of the Virginia Wine Country bike tour itinerary, including links to interactive route maps with elevation profiles. PLEASE NOTE: All of our routes can be adjusted to make them more or less challenging. With the support of our SAG vehicle, we can provide a variety of starting and finishing points on each day to provide a customized ride.

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For those who arrive in Charlottesville early and want a taste of what lies ahead, enjoy an optional afternoon ride in the hills west of Charlottesville. Explore the University of Virginia campus and the pedestrian mall on historic Main Street before dining downtown at one of Charlottesville's best restaurants.

OVERNIGHT ACCOMMODATIONS: Oakhurst Inn (Charlottesville)

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Ride incredibly scenic farm roads that become more impressive with each turn, a perfect introduction to the beauty (and hills!) of rural Virginia. Sample the award-winning wines of White Hall Vineyards after the ride. Enjoy the view overlooking the Shenandoah Valley along with the complimentary wine and cheese happy hour at the Iris Inn before dinner in Waynesboro.


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Take in the calendar-worthy views of the Shenandoah Valley, with its fertile farmland framed by a Blue Ridge Mountain backdrop, on a hilly 34-mile ride. Enjoy an excellent lunch on the lovely patio of CrossKeys Vineyards followed by wine tasting. Cap off the day with dinner at Zynodoa, one of our all-time favorite farm-to-table restaurants.


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Challenge yourself with a monster climb up to the Blue Ridge Parkway, followed by a screaming descent down the other side! Finish another gorgeous day of riding at beautiful Pippin Hill Farm & Vineyards, where we'll have lunch and sample their wines while enjoying one of the best views in Virginia. Savor one last group dinner at another of Charlottesville's finest restaurants.

OVERNIGHT ACCOMMODATIONS: Oakhurst Inn (Charlottesville)


Enjoy one final breakfast in Charlottesville before heading home.

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