Portage Assistance Added to the Islander Regatta

Posted byChristine JohnsonPosted inUncategorized

New for 2026: Mathews County Parks & Recreation Support

Whether you are already registered for this year’s event or have joined us in past years, we wanted to share an exciting update for the upcoming Islander Regatta on Saturday, June 27, 2026.

Mathews County Parks & Recreation Commission will be stationed at the approx 3-mile point along the course to assist paddlers with portaging their boats across the narrow sand spit crossing. Volunteers will be available to help participants safely and efficiently move kayaks, canoes, and paddlecraft during this short transition point on the circumnavigation route around Gwynn’s Island.
Registration is Open

For those of you who have already registered for 2026 — welcome back! We are excited to have you returning for another memorable day on the water.

And for our past participants who have not yet signed up this year — we would love to welcome you back to the Islander Regatta community. The event continues to grow while maintaining the relaxed, scenic, and supportive atmosphere that has made it such a special experience on Virginia’s Chesapeake Bay.

The Islander Regatta offers:
  • A unique circumnavigation of Gwynn’s Island
  • Supported rest stops and safety monitoring
  • Beautiful Chesapeake Bay scenery and coastal wildlife
  • A welcoming paddling community for recreational and experienced participants alike

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