Virginia’s Capital Trail & Williamsburg Bike Tour

On this Virginia bike tour, you’ll spend four days cycling the best of historic Williamsburg, Virginia! Ride through the heart of the American Revolution, explore authentic colonial sites like the Jamestown Settlement, enjoy fine regional wines and kick back for three nights in upscale boutique lodging.

Williamsburg was capital of the Virginia Colony from 1699 to 1780 and played a significant role in the American Revolution. It forms the “Historic Triangle” together with Jamestown and Yorktown, which we visit as well. Its heart is Colonial Williamsburg, a historic district and living-history museum where actors in period costume depict daily Colonial life in the streets, stores and workshops. Williamsburg was named one of the top 15 cities in the U.S. in Travel + Leisure’s “2017 World’s Best Awards” survey.

Enjoy scenic, historic cycling, local wines, shopping and Revolutionary history on this memorable Virginia bike tour.

Day 1:  You will meet your guides today at your hotel or the parking location near the Richmond International Airport. The day begins with a 19-mile ride through historic Richmond visiting many historic sites along the way, with a stop for lunch along the way. We’ll then make our way to the Omni Richmond Hotel for the evening. We’ll have dinner together at one of Richmond’s many fine restaurants. 

* While you will pedal through Colonial Williamsburg, we sadly won’t have time to visit the many attractions. If you would like more time in Williamsburg, we suggest that you schedule a day before or after your bike tour to explore! 

Day 2:  Pedal the paved Virginia Capital Trail to two nights at an upscale Williamsburg lodging, Cedars Bed & Breakfast. If you’d prefer a high-mileage day, ride the whole 52.5-miles route. Today we will also tour the Jamestown Settlement. Near the site of the original colony, Jamestown Settlement tells the story of 17th-century Virginia; from the arrival of English colonists in Jamestown in 1607 to the cultural encounters and events that planted the seeds of a new nation. You’ll enjoy dinner on your own in Historic Williamsburg. 

Day 3: Today starts with a ride across the James River on the Jamestown-Scotland Ferry into Surry County. Once on the south side of the river, we will ride the rural roads through portions of Chippokes Plantation State Park. Chippokes Plantation is one of the oldest continuously farmed properties in North America, having just celebrated its 400th anniversary. After this short but beautiful ride, we’ll jump back on the Ferry to the north shore where we will have the option to ride around Jamestown Island or explore the settlement some more. After the ride, clean up at your lodging, and meet then everyone for our last dinner as a group at a local Williamsburg restaurant.

Day 4: Our final ride takes us along the Colonial Parkway, a 31.5-mile scenic roadway stretching from the York River at Yorktown to the James River at Jamestown. It connects Virginia’s historic triangle: Jamestown, Williamsburg, and Yorktown. This route is the perfect avenue to enjoy the natural and cultural beauty of Virginia. Our ride ends after 34 miles at the American Revolution Victory Center at Yorktown, the site of the last major battle of the Revolutionary War. Take your time to explore this historic spot before our final shuttle back to the airport!