Jamestown is part of the ‘historic triangle’ of Colonial National Historical Park that also includes includes Yorktown and Williamsburg.  Jamestown is the site of the first English settlement in North America, in 1607, and also the first arrival of African Americans (in 1619). It is currently both a historic site and also an active archaeological dig. One can do a quite nice run in Jamestown, combining the ‘walking tour’ of Historic Jamestowne and the scenic Island Drive around Jamestown Island. Also nearby is the Jamestown terminus of the Virginia Capital Trail, which extends for 50 miles to Richmond.  Note: See website for hours and admission fees

Jamestown Run. Start with the ~1.5 mile ‘walking tour’ of the Historic Jamestowne Settlement. You might have to run/walk this section. Then, you can enjoy a loop of Island Drive. It’s mainly wooded, combination of paved and dirt surface. Although there’s no sidewalk, there isn’t a lot of traffic and the road is popular with pedestrians and cyclists. There’s shorter ~3 mile loop (using the cutoff road), and a longer ~5 mile loop. So this can be a run of up to 6.5 miles, over rolling hill terrain. Note: Access to Island Drive is only during Park opening hours and admission fee is required. 

Virgina Capital Trail. This historic multi-use trail runs for 50 miles between Jamestown and Richmond. The Jamestown terminus of the trail is at the Jamestown Settlement parking lot. The first few miles from Jamestown is lovely, especially over the section over the Chickahominy River. Most of the trail parallels John Tyler Hwy (SR 5). 

Colonial National Historic Parkway. This is part of the National Park and runs for 8 miles east and north to Williamsburg (the first part of it along the James River) and then another 12 miles west to Yorktown. We don’t recommend it for running, because there’s no sidewalk/shoulder, and traffic can be heavy.