VIRGINIA BIKE TOURS

Virginia bicycle tour destinations

Virginia may be for lovers, but it is definitely for lovers of great cycling.  Whether you prefer the more challenging country roads of the Shenandoah Valley or the flatter trails and roads around Historic Williamsburg, we have a great cycling vacation to share with you.

Virginia Tours from Carolina Tailwinds

Southern Shenandoah

Breathtaking Blue Ridge overlooks, pastoral valley farms, and winding mountain passes provide the setting for this incredibly diverse tour.  Jagged Alleghenies on the west and the awesome Blue Ridge on the east define the boundaries of the fertile agricultural Shenandoah Valley.

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Virginia Blue Ridge

Come ride the Blue Ridge Mountains.  Southwestern Virginia is home to beautiful sections of the Blue Ridge Parkway, the charming arts community of Floyd, bustling Blacksburg and mile after mile of beautiful road cycling.

This itinerary is great for the cyclist who doesn't care for van shuttles.  There is only one short shuttle built into the itinerary.  Otherwise, bike inn-to-inn each day!

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Colonial Virginia

This is a new and improved itinerary for this destination.  Dates will fill quickly!

Eastern Virginia is rich in history:  Home to the first successful English colony in America, the current capital city,  and the incomparable living historic park that is Colonial Williamsburg.  This itinerary also includes Smithfield, Virginia - a picturesque small town on the south side of the James River with lots of heart and much to love!  Bike routes on gently rolling hills and flat terrain connect these sites and more. 

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Tours

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2025

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The Carolina Tailwinds Experience