Colonial Williamsburg Bike Tour

Cycle Virginia’s Historic Triangle!

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.

Tour Highlights

Virginia Capital Trail

Tour the Jamestown Settlement

Williamsburg Winery

Yorktown Battlefield

Lodging Options

Berkeley Hotel

Wedmore Place

Day 1:  The group will meet today at your hotels and/or the group parking location near the Richmond International Airport.  The day begins with a 21-mile ride through historic Richmond visiting many historic sites along the way, with a stop for a café lunch along the way. We’ll then make our way to the Berkeley Hotel for the evening. The historic, upscale Berkeley is at the western edge of the historic Shockoe Slip. Stroll the cobblestone streets, window-shopping and taking in the Revolutionary architecture! 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 of lodging at the Wedmore Place at Williamsburg Winery.  If you’d prefer a high-mileage day, ride the whole 55.7-miles route. An optional van shuttle will take riders to an alternate starting point for a shorter ride of 35 miles. 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. We’ll have dinner together at the highly-acclaimed Café Provençal.


Day 3:  Today’s ride starts from the Wedmore and takes us into Surry County via the Jamestown-Scotland Ferry across the James River. Ride the rural roads of Surry Country to a picnic lunch at Chippokes Plantation State Park, with an optional visit to the Mansion House and
Farm Museum. Take the ferry back to the north shore and explore Jamestown Settlement or Historic Jamestowne, part of Colonial National Historical Park. You can either ride a lot or a little on Jamestown Island, then ride back to lodging. After the ride, clean up at the Wedmore for a late-afternoon wine tasting and winery tour. If you’d like to explore Williamsburg for dinner tonight, a van shuttle is available to take you there!


Day 4: Our final ride takes us along the Colonial Parkway, a 23-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! 

Great tour for history buffs and bicycle riders!

~Don & Jennifer Mayer

Trip Information


Trip Length - 4 Days

New York Finger Lakes Bike Tour
Tour Type
Road Bike
Tour Rating
New York Finger Lakes Bike Tour Elevation
Route Overview

Daily Mileage

Check In Location
Richmond, VA
Jamestown to Yorktown map
Tour Area
SAG Vehicle New York Finger Lakes Bike Tour
Support & Gear Vehicle

Minimum Age


3 Breakfasts | 4 Lunches | 2 Dinners

  • PP Double Occupancy

  • Single Supplement*

  • Standard Bike Rental


*This is required if you are traveling solo or if you are traveling with someone but require separate beds.


Select your departure date and click to reserve your bike tour!

  • 2021 Dates
  • If your desired date is no longer available, to be placed on a waitlist or request a private departure, please follow the ‘Request Itinerary’ button below & send us a message or call our office number below to speak to one of our reservation staff. We may open additional tours, and those on the waitlist receive priority on future tours