Hampton Roads, Virginia, is a coastal gem where the Elizabeth, James, and Nansemond rivers meet the Chesapeake Bay and Atlantic Ocean. This region, which includes cities like Norfolk, Chesapeake, and Hampton, offers a variety of motorcycle rides that no adventurous rider should overlook.
Though Virginia’s Blue Ridge Mountains often steal the spotlight, the Tidewater region offers unique routes that are perfect for riders. Next time you’re in the area, explore these trips around Hampton Roads for an unforgettable ride.
The Chesapeake Bay Bridge-Tunnel
The Chesapeake Bay Bridge-Tunnel links Norfolk and Virginia Beach to Townsend and Capeville at the northern tip. Celebrated as one of the modern world’s engineering wonders, this toll bridge and tunnel offer views of the Chesapeake Bay. One highlight of this trip is how the road plunges beneath the waves before resurfacing on the bay’s Eastern Shore. Nearby, explore historic Cape Charles with its charming shops, beaches, and renowned lighthouse.
Alternatively, you can visit Chatham Vineyards in Machipongo. You can also check out Kiptopeke State Park, known for its birdwatching and scenic trails, before continuing your ride north into Maryland.
Colonial Parkway
The Colonial Parkway is a 23-mile scenic route that connects Jamestown, Williamsburg, and Yorktown, three of Virginia’s most historic sites. Starting near the Jamestown Settlement, the parkway offers a peaceful ride through lush forests, rolling fields, and along the banks of the James and York rivers. Riders will appreciate the lack of commercial traffic, allowing for a more relaxed journey. Along the way, you can explore landmarks such as Jamestown Island, Williamsburg’s colonial district, and the Yorktown Battlefield, where the parkway ends.
Capital Country Byway or Nickel & Dime Drive
This loop takes you from Williamsburg, the colonial capital of Virginia, to the state’s modern capital of Richmond. Start in Williamsburg and take Route 5 to Richmond. As you ride, keep your eyes open for bald eagles, which commonly nest around the area. Also called Nickel Road, Route 5 passes three former presidents’ homes. There are also many Civil War battlefields to visit along the route, including Richmond National Battlefield Park.
To return to Williamsburg, head south on Dime Road (Route 10) and cut across to Jamestown on Route 31 with a quick ride on the Jamestown Ferry.
George Washington Memorial Parkway
Head north toward D.C. for a ride along the Potomac River, and be sure to stop at any of the historic sites along this 25-mile stretch of road to stretch your legs. The route includes several can’t-miss historical opportunities, such as Mount Vernon, numerous colonial home museums, and several old cemeteries.
Highlands Parkway to Damascus
The Highlands Parkway, part of Route 58, offers a stunning ride from Portsmouth to Virginia’s western border. The most scenic stretch begins near Meadows of Dan, where the road winds through charming small towns like Galax and Damascus. Damascus, known as “Trail Town, USA,” intersects with the Appalachian Trail, where hikers often mingle with locals. Continuing west, you’ll reach Cumberland Gap National Historical Park, a site rich with history and breathtaking views. A hike to Pinnacle Overlook rewards you with a panoramic vista of Virginia, Tennessee, and Kentucky.
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