Kayaking along the canal draws participants to both the Paddle for the Border and the KayaXpedition events.

The great outdoors surrounds Chesapeake, Va., with the Virginia Beach oceanfront and the Great Dismal Swamp just minutes away. And, bustling downtown Norfolk is nearby, too. It’s a location that leads to unique family moments.

Whether you’re paddling on a board, canoe, or kayak, or watching along the 7 1/2 –mile route, the annual Paddle for the Border is a highlight of the outdoor season in Chesapeake. It all starts at 8:30am on May 5, as paddlers launch from the Dismal Swamp State Park in South Mils, N.C., and head to the boat ramp on the Dismal Swamp Canal Trail in Chesapeake.

The historic waterway is celebrated by the event that puts hundreds of kayaks and canoes into the calm canal waters for a leisurely three-hour journey through the Atlantic white cypress trees that line the banks. Deer, river otters, and even black bear watch the procession while migratory birds pass overhead along the Atlantic flyway.

George Washington’s land company surveyed this swampy terrain in 1763 before commissioning the canal’s construction. Slaves took advantage of the wetlands while traveling north to seek freedom.


Want to participate?

The 300 slots for participating paddlers fill up quickly, so your best bet is to watch for the annual registration to open up in April.

Participants unload their craft at the launch point, and then drive back to the finishing point where shuttle service will take them back for the actual launch. Participants who register receive the shuttle service, breakfast, lunch, and a commemorative hat or T-shirt.

The event is open to both adults and youth, but youth participants must be accompanied by an adult. Those ages 12 to 17 may paddle in a separate boat, but must be accompanied by an adult in another boat. Those under 12 must be accompanied by an adult in the same boat.


More this spring

The KayaXpedition that takes place June 9–10 is a perfect family festival for adventurous families who like to kayak, canoe, or use a stand-up paddle board. Reservations are required for most of the events.

The Chesapeake Jubilee on May 17–20 is a combination carnival and food fest with the annual shrimp feast and barbecue cook-off competition. It also features fireworks, music, rides, and games for the whole family.


Learn more

Chesapeake Tourism: visitchesapeake.com

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