Islander Regatta 2025

Saturday, June 28, 2025 8:00 AM (GMT-4) - Saturday, June 28, 2025 12:00 PM (GMT-4)

Event info
Sport: Paddling
Location: Gwynn, VA, United States
Registrations: 83
Registration closes: Thursday, June 26, 2025 11:59 PM (GMT-4)
Organized by: Mathews Outdoor Club
Event website: https://islanderregatta.com
Event notes

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).

 

New Swag: Island Themed Shirts.Custom shirts with the event logos will be ordered 2 weeks prior to paddle day, June 14. If you sign up on or after June 14, the limited number of extra shirts will be available on a first-come-first-serve basis.

Show more Show less

Contact organizer

Use this form to send an email to the organizer.

Your name
Your email address
Confirm email address
Message to organizer
Send

The entry fee varies - make selections to show the fee.
Entries are limited - make selections to show number available.
Webscorer account
Who are you registering?
Team name
 
First name
 
Last name
 
Email address
 
Age on event date
Gender
 
Phone #
 
Address
 
Emergency contact name
 
Emergency phone #
 
City
 
Zip code / Postal code
 
State / Province
 
Country
 
Select "Individual"
 
Event entry fee TBD
Each paddler - even if part of a multi-person boat - needs to register separately and select appropriate shirt size.
Shirt size (Unisex)
 
 *
I understand that this event is limited to participants age 14 or older.
 
 *
Processing fee
--
Total
--
Please review the waiver provided by the event organizer and click the check box below to accept it. Print waiver

Physically Able. I have read the event description, understand the course conditions and believe myself capable of completing the self-powered paddle around Gwynn’s Island.

 

Self Conduct & Race Crew Instructions. I agree to adhere to the school and council rules of conduct and sportsmanship while participating in this event. I will follow instructions of the race crew including – but not limited to – the keeping the required equipment (PFD) with me during the event.

 

Medical Insurance Waiver. I understand that neither the Islander LLC nor the Mathews Outdoor Club provide any registrant medical or hospitalization insurance whatsoever, and hereby waive any and all claims against the Islander LLC, the Mathews Outdoor Club or any other person affiliated with these entities and sponsors for injuries sustained while watching or participating in this event or traveling to and from event. Health Precautions. I acknowledge that certain health risks are inherent with public activities and that the event organizers will provide reasonable safety precautions (such as providing space/room for social distancing) at the event start/finish areas. While the participants are not within the start/finish areas, it will be each participant’s responsibility for adhering to the safety precautions.

 

Photography Waiver. I agree that photographs taken of my child or me while participating in this activity may be used for publicity.

Name of parent or guardian who approves this activity