​​In early spring hundreds of paddlers launch their vessels into the Dismal Swamp Canal’s dark, mirrored waters. This historic waterway serves as the backdrop for Paddle for the Border, an annual 7.5-mile paddling excursion to the North Carolina/Virginia border.

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This annual event highlights the canal’s rich history, which dates to 1763 when George Washington’s land company first surveyed the swamp before commissioning the waterway’s construction. In the 19th century, the canal’s dense wetlands provided refuge for those enslaved traveling the Underground Railroad before continuing their journey north.

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The fee is $65 per person.  After enjoying a pre-launch "grab-and-go" breakfast at the Dismal Swamp State Park, in South Mills, NC, paddlers embark on the leisurely three-hour journey to cross the state line. They finish the day out with a picnic lunch on grounds of the Dismal Swamp Canal Trail at the Great Dismal Swamp Boat Ramp at Ballahack Rd. in Chesapeake, VA. Registration fills quickly!

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Registration available (online & in-person) January 7th, 2026 at 9am!

Pre-registration is required for this event.  This event is limited to 375 paddlers.  

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​Registration Open

 

Paddle For the Border Online Registration/City of Chesapeake

 

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Paddle For the Border Registration Form & Waiver

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FOR MORE INFORMATION:

Paddle for the Border Brochure 2026

Paddle for the Border FAQ 2026

2023 Where is CD Now? (one woman's PFTB experience)

Phone: 252-771-8333

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Kayak Rentals/Outfitters 2026​​

• Dismal Swamp State Park/ 252-771-6593

•  Chesapeake Parks, Recreation & Tourism/ 757-382-6411

• OBX Adventure/ 252-489-8146 (Click the link & Book Now)

• Adventure Kayak & SUP/ 757-237-8776

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2025 Paddle for the Border Memories 

(Photography: Camden TDA/Alley Williams)

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