Virgina's Route 5 Scenic Byway , between Interstate 295 east of Richmond and Jamestown, provides your pathway for exploring the historical legacy of 1607, from the establishment of Jamestown and the introduction of Virginia's plantation economy to the Civil War and the end of slavery. Four centuries of history is yours to discover on your approach to Jamestown.

The trail begins in Henrico County, continues through Charles City County and terminates in James City County. These are three of Virginia's original eight shires established in 1634. The trail includes three National Park Service sites, seven open-to-the-public National Historic Landmark and National Register plantations, three county parks, and 37 state and local historic highway markers. The final segment of the trail includes Greensprings Road, the 17th-century road that led from Governor Berkeley's plantation to Jamestown, one of America's oldest roads.

The trail begins east of Richmond in Henrico County. The history of the Civil War is the focus of the first two sites, Henrico County's Deep Bottom Park and the Malvern Hill Unit of the Richmond National Battlefield Park . The Civil War brought an end to slavery and the plantation economy that produced the grand plantation houses located further east in Charles City County along the James River.

Berkeley plantation offers house and grounds tours daily, while Edgewood , North Bend , Piney Grove , Sherwood Forest and Westover plantations offer self-guided gardens and grounds tours daily and group house tours by appointment. Belle Air plantation is open for Historic Garden Week and for group tours by appointment. All of the plantations also offer many special event tours throughout the year.

At the midpoint of the trail is Charles City County's Lawrence Lewis Jr. Park at the site of Grant's Crossing of the James River. Just two miles east is Charles City Court House, the location of the actively used 18th-century courthouse and the Charles City County Center for Local History, a research center that is of interest to genealogists and historians. A short drive on Route 155 leads visitors to the historical marker commemorating the birthsite of Lott Cary , America's first African-American missionary, and a short drive north on Route 618 is the Adkin's Store community, home of the Chickahominy Tribal Center , where the annual Chikahominy PowWow takes place.

Visitors along the trail may enjoy elegant regional cuisine in Charles City County at Indian Fields Tavern , a restored Victorian farmhouse. Landmark plantation bed and breakfast lodging is available in Charles City County at Piney Grove, North Bend and Edgewood plantations.

Continuing east toward Williamsburg, the Chickahominy River is crossed on Barrett's Ferry Bridge. Immediately after crossing the bridge will be James City County's Chickahominy Riverfront Park . Recreational opportunities, such as fishing boating, swimming and wildlife watching, abound at this beautiful riverside location.

Three miles east, at the traffic light, turn right to continue on Route 5 East. Just slightly more than a mile, turn right onto Greensprings Road. This ancient road continues two miles to Jamestown Settlement . Here, visitors can explore a series of exhibits, a re-creation of Jamestown Fort and replicas of the ships that brought Jamestown founders.

Just a quarter mile east on the Colonial Parkway is Historic Jamestowne , the original settlement site, which is jointly administered by the National Park Service and the Association for the Preservation of Virginia Antiquities . Archaeological investigations are currently revealing James Fort and other important early features of America's first permanent English settlement in the New World.