Annual 9 mile paddling event for non-motorized craft.

Circumnavigating one of Virginia’s few inhabited islands: Gwynn’s Island in Mathews County.

2023 Event is Saturday, June 24th
8am – 1pm

Islander Regatta water support is provided by the US Coast Guard Station at Milford Haven and by the USCG Auxiliary Flotilla 66, Mathews County. READ MORE

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).

Check out the Mathews Co Visitor Information Center (MCVIC) website for useful information like visitor accommodations & kayak rentals.

Video was filmed & produced by Gywnn’s Island resident Tab Warwick.


The Mathews Outdoor Club (MOC) is a nonprofit organization located in Mathews County Virginia dedicated to promoting outdoor fitness to area residents & visitors.

Farmboards LLC is a designer & manufacturer of custom paddleboards with its headquarters in Mathews County.

– Christine Johnson (MOC) and Will Berg (Farmboards) are co-directors of the Islander Regatta and have completed this 9-mile paddle a few times.

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.

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.

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.

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.



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