Extra Rides

There are too many nice rides around Williamsburg to fit into three days, so we have put together six Extra Rides for those who arrive early and/or leave later. There are both remote and Williamsburg Woodland Hotel starts, including the Yorktown Battlefield and rides across the James River in Surry and Isle of Wight Counties. Ride lengths range from 16 to 46 miles.

Williamsburg Rides – Hotel Start

  • Williamsburg Explorer – 16 Miles. This ride takes you through the College of William & Mary, old and new Williamsburg neighborhoods, and two City Parks. College Landing Park was one of two colonial ports established with Williamsburg in 1699. Redoubt Park interprets Redoubt #1 of Williamsburg’s Defensive Line and Williamsburg’s role in the Civil War.
  • Jamestown/Winery Loop – 25 Miles. This ride takes you from Williamsburg to Jamestown Island and the seven-mile Jamestown Island Tour Road loop. Following Jamestown Island, the route takes you along the Colonial Parkway to Treasure Island Road and on to the Williamsburg Winery where you can have a wine tasting and/or lunch or dinner. Then back to the Hotel along Jamestown Road. The Jamestown Island loop is a fee area, and requires purchasing a ticket at the Jamestown Island Visitor Center ($14 for the Tour Roads and Historic Jamestowne, good for 14 days, and also includes the Yorktown Battlefield Visitor Center and Tour Roads) or having a National Park Service Senior Pass (plus $5 for Historic Jamestowne). It is a requirement of the National Park Service that cyclists ride single file on the Colonial Parkway. This rule is enforced and they do give out tickets.

Yorktown Rides – Hotel and Remote Starts

  • Yorktown + Battlefield – 37 Miles. This ride starts at the Hotel and takes Penniman Road and the Colonial Parkway to the Yorktown Visitor Center (1000 Colonial Parkway, Yorktown, VA 23690). The route then takes the scenic Tour Roads around the Yorktown Battlefield where the American Revolution was won. Following the battlefield tour, the route goes into Yorktown where you can have lunch at one of the six restaurants along the waterfront. The Yorktown Visitor Center and the Tour Roads require purchasing a ticket at the Visitor Center ($7 and good for 14 days, and also includes admission to the Jamestown Island Tour Roads) or having a National Park Service Senior Pass. It is a requirement of the National Park Service that cyclists ride single file on the Colonial Parkway. This rule is enforced and they do give out tickets. This ride has a total of 19.6 miles on the Colonial Parkway (compared with 7 miles on the Sunday rides) which has a rough concrete aggregate surface. Many cyclists will say that this is too many miles on the Colonial Parkway for a single ride – so be forewarned. The Colonial Parkway from Williamsburg to Yorktown is also a commuter route, and traffic is much heavier than between Williamsburg and Jamestown.
  • Yorktown Battlefield Loop – 12 Miles. This short Remote Start ride starts at the Yorktown Visitor Center (1000 Colonial Parkway, Yorktown, VA 23690) and takes the scenic Tour Roads around the Yorktown Battlefield where the American Revolution was won. The Yorktown Visitor Center and the Tour Roads require purchasing a ticket at the Visitor Center ($7 and good for 14 days, and also includes admission to Jamestown Island Tour Roads) or having a National Park Service Senior Pass. We suggest that you first tour the exhibits at the Yorktown Visitor Center and then ride the Tour Roads.

Surry County and Isle of Wight County Rides – Remote Start

  • Chippokes Loop – 25 Miles. This Remote Start ride starts at the Jamestown Settlement parking lot (2110 Jamestown Rd, Williamsburg, VA 23185) – park in the section of the parking lot furthest from the Jamestown Settlement Visitor Center. You ride your bike onto the free Jamestown-Scotland Ferry and ride the ferry to Surry County. After leaving the ferry, the route goes to Chippokes Plantation State Park (695 Chippokes Park Rd, Surry, VA 23883), and then over scenic rural roads to the one traffic light town of Surry. From Surry it is a straight shot back to the ferry, with an option for a lunch or dinner stop at the Surry Seafood Company (closed Mondays).
  • Smithfield Loop – 46 Miles. This is one of Reed & Karen’s favorite rides. Cross the James River on the free Jamestown-Scotland Ferry and drive to the Remote Start at Chippokes Plantation State Park (695 Chippokes Park Rd, Surry, VA 23883). This ride explores the beautiful country roads of Surry County and Isle of Wight County and travels to the picturesque town of Smithfield. On the way into town the route takes you past the Smithfield Ham processing plant. There is a lunch stop at mile 26.1 at the Smithfield Station Restaurant (be sure to eat on the rear deck overlooking the Pagan River). There are more scenic roads on the way back to Chippokes Plantation State Park, and you will ride by Bacon’s Castle, the oldest brick dwelling in North America.

Detailed maps and cue sheets and downloadable .gpx files will be provided closer to the Rally. All rides were laid out using RideWithGPS.

If you have questions about the routes, email Reed at reednester@gmail.com.