What better way to spend a long weekend than to explore historic Virginia! This is a perfect trip for someone new to bicycle travel and experienced travelers alike. Visiting small towns like Jamestown and Williamsburg, we’ll have a chance to explore places like the Yorktown Battlefield, Colonial Williamsburg, and Historic Jamestowne. We’ll immerse ourselves in the history of the area as we ride rolling rural roads past farms and pastures, and enjoy the views that come with riding along the coast. We’ll even spend time riding on the iconic TransAmerica Bicycle Trail and possibly see some cyclists starting (or ending) their epic cross-country journey. After this long weekend is over, you may even be setting your sights on your very own epic adventure!
"Cycling just gets better and better as you get older."
Day 1. Williamsburg to Surry, Virginia, 22 miles
As we embark on four days and three nights of our long weekend, we will ease ourselves into the experience with healthy doses of scenery and adventure, taking us through Colonial Williamsburg and into Jamestown where we’ll cross the James River by ferry. We’ll continue to our campsite for the night, tucked in on Cobham Bay.
Day 2. Surry to Williamsburg, 39 miles
We’ll take a new route through rolling terrain heading back to the James River ferry on nice country roads through Surry County. Arriving back in Jamestown, consider a visit to the Historic Jamestowne Visitor Center before jumping on the Virginia Capital Trail to our next overnight spot, which is once again by the water. On part of today’s ride, you’ll be the TransAmerica Bicycle Route, which starts or ends in nearby Yorktown.
Day 3. Williamsburg to Newport News, 34 miles
With one more pass through Jamestown onward to our next overnight, you’ll be able to take in anything you may have missed. We’ll ride part of the Colonial Parkway, which connects the Yorktown Battlefield, Colonial Williamsburg, and Historic Jamestowne.
Day 4. Newport News to Williamsburg, 29 miles
We’ll spend time today riding trails through the largest park in Newport News before taking the Colonial Parkway back to Williamsburg. Be sure to take a break and check out the sights as you pass through Yorktown — maybe you’ll even catch a bicycle tourist starting or ending their cross-country journey! We’ll return to Williamsburg, accomplished and maybe a little tired, but excited to plan our next adventure!