# VA 5 & the Colonial Parkway *plantation row to the first peninsula* VA 5 & the Colonial Parkway is a ~90-mile back-roads route from Richmond to Yorktown on VA 5 and Colonial Pkwy, driven in 1–2 days, that stays off I-64 through the Atlantic Coast. - **Drive:** Richmond → Yorktown - **Distance:** ~90 mi - **Days:** 1–2 - **Highways:** VA 5, Colonial Pkwy - **Avoids:** I-64 - **Region:** Atlantic Coast - **Themes:** History & Markers, Battlefields: Other Wars, Vineyards & Wine Trails, Natural Beauty Two of America's oldest roads share one peninsula: VA 5 down the James past the river dynasties (Shirley, billed as America's oldest family business; Berkeley with its 1619 Thanksgiving claim and the bugle call Taps, composed on its grounds in 1862; Tyler's Sherwood Forest), then the Colonial Parkway's brick-tinted miles stitching Jamestown's actual 1607 fort to the siege lines at Yorktown. Four centuries in ninety minutes of driving, if you refuse every temptation, which you will not. Markers: The Parkway is its own interpretive system; the plantations post their histories, enslaved communities included, at the gates. ## The drive, segment by segment ### Plantation Row *Richmond → Sherwood Forest · ~35 mi* Shirley, Berkeley and Westover in procession along the river road's oak tunnels. Stops: - **Shirley** (Charles City) · History & Markers — A 1613 land grant still farmed by the same family eleven generations on, billed as the oldest family business in North America; the flying staircase has no visible support and no equal. - **Berkeley** (Charles City) · History & Markers — Claims America's first official Thanksgiving (1619), grew two Harrison presidents, and heard Taps first: the call was composed here during the army's 1862 encampment. - **Sherwood Forest** (Charles City) · History & Markers — John Tyler's home, said to be the longest frame house in America, and still owned by Tylers; the grounds walk past a president's actual privacy. ### Jamestown *Sherwood Forest → Williamsburg · ~30 mi* The ferry option, the island fort, and the archaearium's recovered lives. Stops: - **Historic Jamestowne** (Jamestown) · National Parks — The real 1607 site: the fort's rediscovered footprint, active digs, and the archaearium's recovered settlers, told bones-first. ### The Parkway to Yorktown *Williamsburg → Yorktown · ~25 mi* No trucks, no billboards, 45 mph of brick-red concrete to the surrender field. Stops: - **Colonial Williamsburg edge** (Williamsburg) · Small Towns — The Parkway tunnels directly beneath the restored capital; surface for Duke of Gloucester Street or save the full immersion for its own day. - **Yorktown Battlefield** (Yorktown) · Battlefields: Other Wars — The 1781 siege lines and Surrender Field where Cornwallis's army stacked arms; the Revolution's endgame, walkable in an afternoon. ## Tips and best time to go - The Parkway bans commercial traffic and holds 45 mph; it is the point, not the delay. - The Virginia Capital Trail parallels VA 5 the whole way if you'd rather do plantation row by bicycle. ## Worth a detour - **Upper Shirley Vineyards** — Wine on the James beside Shirley's fields; the porch view alone justifies the tasting. - **Fort Pocahontas** — A Union earthwork at Wilson's Wharf built and defended by US Colored Troops in 1864; preserved privately, open by event. ## Frequently asked questions ### How long is VA 5 & the Colonial Parkway and how many days does it take? VA 5 & the Colonial Parkway is about 90 miles and takes 1–2 days at a back-roads pace. ### Where does VA 5 & the Colonial Parkway start and end? It runs from Richmond to Yorktown. ### Which highways does VA 5 & the Colonial Parkway follow? It follows VA 5 and Colonial Pkwy. ### Which interstate does VA 5 & the Colonial Parkway replace? It avoids I-64, using VA 5 and Colonial Pkwy instead. ### How many stops are on VA 5 & the Colonial Parkway, and what are the highlights? 6 stops are mapped, including Shirley, Berkeley, Sherwood Forest, Historic Jamestowne and Colonial Williamsburg edge. ### Which ready-made itineraries include VA 5 & the Colonial Parkway? Tidewater & the Outer Banks (4 days) and Cradle & Surrender: Jamestown to Appomattox (3 days). ## Ready-made itineraries using this route - [Tidewater & the Outer Banks](https://dixieroadtrip.com/trips/tidewater-outer-banks) — 4 days, ~430 mi - [Cradle & Surrender: Jamestown to Appomattox](https://dixieroadtrip.com/trips/cradle-and-surrender) — 3 days, ~260 mi ## Connects with - [Lee's Retreat](https://dixieroadtrip.com/routes/lees-retreat) — Petersburg → Appomattox - [US 13: The Eastern Shore](https://dixieroadtrip.com/routes/eastern-shore-13) — Cape Charles → Chincoteague - [The Northern Neck](https://dixieroadtrip.com/routes/historyland-neck) — Fredericksburg → Irvington --- Canonical URL: https://dixieroadtrip.com/routes/va5-colonial Publisher: Dixie Media (Dixie Road Trip, https://dixieroadtrip.com/) Last updated: 2026-10-05