Islander Regatta 2025

Annual 9 mile paddling event for non-motorized craft. Circumnavigating one of Virginia’s few inhabited islands: Gwynn’s Island in Mathews County.

With its origins as a fun summer challenge for a group of friends, the Islander Regatta is opening its door to more participants.

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.

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 in 2003 during Hurricane Isabel and was forced to close.

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 and USCG Auxiliary Flotilla 66, 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.

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 were ordered.Custom shirts with the event logos were ordered 2 weeks prior to paddle day, June 14. A limited number of extra shirts will be available on a first-come-first-serve basis. No refunds - we have started making event-related purchases so can no longer offer refunds of registration fees.