Long Weekend

Cradle & Surrender: Jamestown to Appomattox

3 days · ~260 miles · from Williamsburg

Open this trip in the map →

Start
Williamsburg
Days
3
Distance
~260 miles
Length
Long Weekend
Themes
🏛️ History

The bookends of American history in one Virginia weekend: the first permanent English colony and the Yorktown victory that won independence, then the plantation road to Petersburg and the courthouse where the Civil War ended.

This trip chains: VA 5 & the Colonial Parkway · Lee's Retreat

Day by day

Day 1: The Colonial triangle

Historic Jamestowne where it began in 1607, the edge of Colonial Williamsburg, and the Yorktown battlefield where Cornwallis surrendered — the Colonial Parkway between them, no billboards allowed. Overnight Williamsburg.

Day 2: The James River plantations → Petersburg

VA 5 west past Sherwood Forest, Berkeley and Shirley plantations along the James, then Petersburg: Pamplin Park and the trenches where the long siege finally broke. Overnight Petersburg.

Day 3: Lee's Retreat → Appomattox

Follow the 1865 retreat west — Five Forks, Sailor's Creek, the High Bridge, and Farmville's Moton Museum of a later fight for freedom — to Appomattox Court House, where it all came to an end.

More itineraries

Browse all 37 ready-made trips → · All 85 routes →