The perfect summer outdoor activity awaits and it’s called the Islander Regatta…
Picture this – you and your closest adventure buddies throw your SUPs, kayaks or canoe in the pickup and set out on the water for a morning paddle in the waters of one of Virginia’s only inhabited islands – Gwynn’s Island. You can be there for the laughs, or you can come competitively, but regardless this memorable event is calling your name on June 27th, 2026.
Hosted around beautiful Gwynn’s Island, the Islander Regatta is a 9-mile paddling event. Kayaks, paddle boards, canoes, racing shells, and other non-motorized boats are all welcome, making it less about competition and more about sharing the experience.
The annual Mathews Outdoor Club Islander Regatta has quickly become exactly that kind of tradition — part adventure, part celebration, and part floating reunion.
About the Event
June 27, 2026, 8am to 1pm, 633 Old Ferry Road, Gwynn VA
Registration is $65 per person and open to paddlers ages 14 and older.
Paddlers launch from the historic Islander Hotel property and travel through Milford Haven under the iconic swing bridge, along the Chesapeake Bay shoreline, and into the Piankatank River before returning back to shore.
Along the route are rest stops with music, refreshments and portapotties, floating rubber duckies, and plenty of encouragement from volunteers and fellow paddlers.
While the scenery is spectacular, participants say the atmosphere is what keeps them returning each year. Friends paddle together, families cheer from boats and docks, and paddlers feel proud of their 9 mile achievement.
The event is fully supported by the U.S. Coast Guard Auxiliary and local volunteer boaters, helping create a safe and welcoming experience even for newer paddlers.
Once you’ve completed the Islander Regatta, stick around to unwind and enjoy post-paddle refreshments, graciously provided by Mathews Family YMCA & One Man Liquor Stand. It’s a perfect way to cool down, relax, and mingle with fellow paddlers while reflecting on the day’s adventure.
“Gwynn’s Island Days” – Weekend Long Fun
This year’s Regatta also pairs perfectly with other Island events happening the same weekend.
Friday, June 26th
Gwynn’s Island Chicken Dinner – Drive by in the drive through for the famous Gwynn’s Island Chicken Dinner with all the fixings! Friday, June 26, 2026, 4:30pm-7:00pm. No pre-sale tickets.
Gwynn’s Island Museum open 1pm to 5pm
Oyster Hatchery Tours & Tastings – Book an oyster hatchery tour to learn how baby oysters get their start in a commercial hatchery. Afterwards, enjoy a tasting of raw and roasted oysters paired with wine.
Nearby Restaurants Open – Hole in the Wall Waterfront Restaurant and The Hatchery Oyster Eatery.
Saturday, June 27th
Gwynn’s Island Festival from 9am to 4pm gives participants even more reason to make a full day of it. Festival has a variety of handmade crafts and local vendors including jewelry, leather, paintings and photography. Festival will also feature live music, Lord Dunmore skits, food vendors, and a kids zone!
The event is located at the Gwynn’s Island Civic Center, 1996 Old Ferry Rd., Gwynn, VA 23066.
Gwynn’s Island Museum open 1pm to 5pm Saturday & Sunday
Nearby Restaurants Open – Hole in the Wall Waterfront Restaurant and The Hatchery Oyster Eatery. ♬ Live Music by Rural Folk Fiasco from 6-8pm!
Whether you’re chasing a personal challenge, looking for a new summer tradition, or simply searching for an excuse to spend a day on the water with good people, the Islander Regatta offers something rare: an adventure that feels both exciting and wonderfully local.
For details and registration, visit Mathews Outdoor Club – Islander Regatta.
Mathews Outdoor Club 