Annual 9 mile paddling event for non-motorized craft.
Circumnavigating one of Virginia’s few inhabited islands: Gwynn’s Island in Mathews County.
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2026 Event is Saturday, June 27th
8am – 1pm
Registration cost is $65 per person not per boat. Tandem kayaks, 8-person racing shells, paddle boats and even dragon boats (!!) are permitted as long as they are human powered, non-motorized. Each paddler must register separately (must be 14 or older). Custom shirts will be ordered two weeks prior (extras available on a first come, first serve basis). We will start making event-related purchases at that time as well, so refunds will no longer offered.
Islander Regatta water support is provided by the US Coast Guard Station at Milford Haven and by the USCG Auxiliary Flotilla 66, Mathews County.
www.DaveTheKayaker.com
Charlottesville, VA
Tel: 804-608-9727
2026 Event Schedule
6:30 – 7:30am check in – our volunteers will be waiting for you at the parking entrance to check you in for the event. They will provide you with a parking pass, event swag, and the course map. Proceed to park after check-in and unload your boat on the lawn – get ready to paddle.
8:00am paddle start – after some brief instructions, paddling will begin. Launch from the sandy beach (water only up to your knees) and begin the counter-clockwise circumnavigation around Gwynn’s Island.
Post-paddle activities – read more about our post-event fun & other island activities such as the annual Gwynn’s Island Festival.
The Course
The Islander Regatta course follows the outline of Gwynn’s Island, which has been described as having a “shark fin” or triangular shape. Paddlers will launch from the beach of The Islander Hotel (see venue section for more info) and proceed counter-clockwise under the Milford Haven Bridge into Milford Sound. Click here for a closer look at the course map.
Briefly portage across a sand section and enter the Chesapeake Bay and continue along the shoreline, around the tip of the island into the Piankatank River, where the final section of the journey ends. Just remember: keep the island to your left!
Expectations
Can I do it? What should I bring? Other important details here.
The Venue
The Islander Hotel is a landmark on Gwynn’s Island – visible for miles from the water and one of the first sights when you cross Milford Haven Bridge onto the island. A once popular destination resort, it is still owned by the same family who built it in the mid 1960s. The Islander suffered extensive damage during Hurricane Isabel and was forced to close.
The Islander owners continue to work on repairs and hope to re-open this iconic establishment one day soon. [Private Property: 633 Old Ferry Road, Gwynn VA].
The Logistics
Safety, Support and other important Stuff. Hosting an outdoor event – in particular one on the open water – requires thoughtful planning & preparation. The Islander Regatta is supported by the US Coast Guard Auxiliary Flotilla 66, which is headquartered at the USCG Station at Milford Haven. Providing shallow water support are volunteer boaters from Mathews County – all of whom are connected via radio communication with the Race Directors throughout the event.
Mathews Outdoor Club 