Start your journey in West Ocean View. Slap the metal fence at the end of Chela Ave while taking in a quick view of the Chesapeake. Run parallel to the beach on Ocean View Ave. After passing 19th Bay Street, continue straight onto E Beach Drive for a scenic loop through the shaded, oak-lined streets of the East Beach neighborhood.
From there, merge onto Shore Drive, taking in the peaceful views of Pretty Lake from the bridge. Settle in for the long haul as you continue along Shore Drive, channeling your inner Navy SEAL as you pass Joint Expeditionary Base Little Creek.
Climb the Lesner Bridge and soak in sweeping views of the Chesapeake Bay—a perfect halfway-point reward. Just past the bridge, turn right on Jade Street, then take a quick left to join the start of the Cape Henry Trail.
This next 6-mile stretch leads you through First Landing State Park—the historic landing site of the English settlers in 1607. The trail is a mix of paved and gravel surfaces, surrounded by pine trees and cypress swamps.
At the eastern exit, pop out onto 64th Street, then head south on Atlantic Avenue. Once you reach 40th Street, you’re on the final stretch: the iconic Virginia Beach Boardwalk. Cruise the last 3 miles on concrete with ocean views and the salty breeze in your face.
Snap a photo with King Neptune, then sprint to the finish and tap the guard rail at the southern end of the boardwalk. You did it—OV to VB.
