Inaugural Island Run Paddle Challenge 2026
Inaugural Island Run Paddle Challenge 2026 sends paddlers onto the waters off Esker Point Beach in Groton on Saturday, August 22, with three courses ranging from a one-mile fun paddle to an eight-mile run toward Fishers Island, followed by an afternoon celebration featuring a barbecue, live music and SURFRIDER sprints.
The new event is designed to work for more than serious racers. Participants can choose a course based on experience and ambition, with divisions for stand-up paddleboards, C1 canoes and K1 kayaks. Everyone who completes the challenge receives a finisher medal, while the fastest paddlers compete for prizes from local businesses.
More importantly, the day benefits a Mystic-based organization with an unusual approach to helping veterans rebuild their working lives: Work Vessels for Veterans.
Three Courses, Three Different Challenges
The Island Run Paddle Challenge starts and finishes from Esker Point Beach, with three distances available.
The Long Course covers approximately eight miles and takes paddlers toward Fishers Island. It begins at 9 a.m. and provides the day’s biggest endurance challenge.
The Short Course is a four-mile route around Ram Island, beginning at 9:30 a.m.
For paddlers looking for something more approachable, the Fun Course covers one mile around Palmers Cove and begins at 10 a.m.
Check-in for all participants begins at 8 a.m.
The three distances make this less intimidating than an event built exclusively around an eight-mile open-water race. Experienced paddlers can tackle Fishers Island while recreational participants can still get onto the water and be part of the day without committing to the longest course.
SUPs, Kayaks and Canoes
The competition is open to several types of paddle craft.
Participants can race using a stand-up paddleboard (SUP), C1 canoe or K1 kayak.
Registration is $99, and all paddlers receive a finisher medal.
First-, second- and third-place finishers will receive gift cards and swag contributed by local businesses.
The event listing currently states that registration ends August 31, although the race itself is August 22. That appears to be a date error in the registration information, so anyone planning to participate should register before race day rather than relying on the listed deadline.
Register for the event by clicking Event Ticketing below
The Party Starts at Noon
You don’t necessarily have to spend the entire day racing.
The competitive portion leads into a noon trophy ceremony, followed by a barbecue and live music at Esker Point Beach.
SURFRIDER sprints are also planned after the barbecue, with Surfrider Foundation Connecticut serving as co-host of the event.
That makes the afternoon portion particularly accessible for friends and family who aren’t getting into a kayak or onto a paddleboard themselves. They can watch the paddlers return, stick around for the awards and then join the post-race gathering.
Supporting Work Vessels for Veterans
The beneficiary gives the inaugural race a strong local connection.
Work Vessels for Veterans is a West Mystic-based nonprofit founded in 2008 to help injured veterans establish businesses and pursue career education by providing them with the equipment they need.
And despite the organization’s name, that doesn’t necessarily mean boats.
A “vessel” can be virtually any piece of equipment that helps a veteran build a livelihood. The organization has supplied veterans with everything from agricultural and construction equipment to tools needed for other small businesses. Rather than issuing loans or simply handing recipients cash, Work Vessels for Veterans purchases or obtains the equipment itself.
The organization reports that it has now assisted more than 4,300 injured veterans, with recipients in all 50 states as well as Puerto Rico and the U.S. Virgin Islands. More than $4.3 million worth of equipment has been provided, helping launch more than 800 businesses and generating an estimated $42 million in economic activity.
That mission has particularly deep roots around Mystic, Groton and Noank. Work Vessels for Veterans was co-founded by people with connections to southeastern Connecticut’s marine industry, and several members of its current board come from Groton, Mystic, Noank and Niantic.
So although the Island Run Paddle Challenge is new, the organization it’s supporting has been doing this work for nearly two decades.
A Day on the Water at Esker Point
Esker Point Beach makes a natural headquarters for the event.
The Groton beach looks across Palmer Cove toward the waters surrounding Groton Long Point, Ram Island and Fishers Island Sound. From there, organizers can send paddlers onto three substantially different courses without moving the event away from its central gathering point.
It’s also a setting where the race and the afternoon celebration fit together particularly well.
Come to compete and you can spend the morning on the water.
Come to support somebody who’s racing and there’s still a barbecue, live music, awards and the waterfront waiting when they return.
Event Details
Event: Inaugural Island Run Paddle Challenge 2026
Date: Saturday, August 22, 2026
Event Hours: 8:00 a.m.–4:00 p.m.
Check-In: 8:00 a.m.
Long Course: 8 miles toward Fishers Island; starts at 9:00 a.m.
Short Course: 4 miles around Ram Island; starts at 9:30 a.m.
Fun Course: 1 mile around Palmers Cove; starts at 10:00 a.m.
Craft: SUP, C1 and K1
Registration: $99
Finisher Medal: All paddlers
Awards: First-, second- and third-place prizes featuring gift cards and swag from local businesses
Trophy Ceremony: Noon
After the Race: Barbecue and live music
Additional Competition: SURFRIDER sprints following the barbecue
Location: Esker Point Beach
Address: 900 Groton Long Point Road, Groton, CT 06340
Beneficiary: Work Vessels for Veterans
Co-Host: Surfrider Foundation Connecticut
More Information
To participate in one of the three paddle courses, use the Event Registration link below.
