Christine Johnson, the founder of the Islander Regatta, sat at a picnic table overlooking the swing bridge leading to Gwynn’s Island. As she gazed out over Milford Haven, the calm waters that separate mainland Mathews County from the island, she reflected on how the event began. “Of course,” she smiled, “it started in COVID.”
After months inside, Christine found herself antsy for outdoor adventures and suggested to a group of friends that they paddle around Gwynn’s Island. On a sunny morning, eight kayaks launched into the peaceful waters of Milford Haven, not knowing what lay ahead.
“We had no idea how far it was [around the island] or how long it’d take us,” Christine recalled. “We just took off.” Her love for nature and the inherent challenge the group trip poses is a constant driving force. “Paddling in the Chesapeake Bay was a little spicy, but what a high.”
The group completed the nine-mile journey, circling the island through three different bodies of water: Milford Haven, the Chesapeake Bay and the Piankatank River. By lunchtime, they were back at The Hole in the Wall restaurant, sharing stories and celebrating their adventure.
That day stuck with Christine, and a year later, she founded the Mathews Outdoor Club (MOC), a nonprofit organization aimed at promoting outdoor activities and sports tourism in Mathews County, Virginia. The MOC hosts several events annually, including 5K runs, open water swimming competitions, micro-triathlons and the Mathews Marathon. But the memory of that paddle lingered.
“All I could think about was, ‘I’ve got to run this to ground and see if I can make it happen.’ ” She was determined to create an event that the entire community could enjoy.
And that’s exactly what she did. What started as a simple day of paddling with friends turned into one of the premier water events in the region—the Islander Regatta.
A group of friends celebrating together post-paddle of the Islander Regatta.
But pulling it off wasn’t as simple as taking to the water. The logistics behind the event were just as challenging as the paddle itself, requiring meticulous planning to ensure safety, secure parking and community support.
Fortunately, the U.S. Coast Guard has a year-round station at Milford Haven, which is supported by the USCG Auxiliary Flotilla 66. Christine worked through the necessary paperwork and received the Auxiliary’s full support for the event.
Janet Thorn and Dan Solari paddling the Islander Regatta together.
She then reached out to the owners of the Islander Hotel, an historic hotel located on a private neck of the island. The Hotel, closed after extensive damage by Hurricane Isabel in 2003, offered the only venue with sufficient parking to accommodate the event. Christine’s persistence paid off. With the support of local families and the USCG Auxiliary, the Islander Hotel graciously allowed the MOC to use their property.
Participant prepares for the 9-mile trip in his flag-flying kayak.
In 2022, the inaugural Islander Regatta was held with 16 paddlers and two local residents manning support boats. The day was a success. The following year word spread, and by June 2023, more than 70 participants arrived on the shores of Gwynn’s Island.
Among the crowd was “Dave the Kayaker,” the owner of West Side Boats in Charlottesville. Dave’s rig was outfitted with GoPro cameras. He paddled the course providing stunning visuals and thoughtful commentary for his YouTube channel.
The Regatta’s popularity grew. In 2024, 125 paddlers in kayaks, stand-up paddleboards and canoes came to participate. “It’s not a race,” Christine emphasized, reflecting the event’s inclusive, non-competitive nature. “Any non-motorized vessel can enter. I’m really hoping to see a dragon boat or scullers in the years to come.”
Safety remains the top priority for the event. The USCG Auxiliary distributes whistles and boat ID tags to participants, as well as providing free boat safety inspections. Private support boats are visible throughout the course to watch for paddlers who may encounter rough water. “The Coast Guard,” Christine assured, “is the final arbiter of safe boating conditions and monitors the weather for the Regatta.”
Kym Ramsey kayaking as she enters the Chesapeake Bay.
Ensuring that paddlers get adequate support, the course includes two rest areas on private properties along the island. The rest stops, marked with giant floating rubber duckies, feature music, refreshments and, most importantly, porta-potties.
The Islander Regatta is a great family fun event for adults and children alike.
Eric Pritchett, meteorologist for News29 in Charlottesville poses with his inflatable rubber duckie during the event.
Kym Ramsey, vividly recalls her experience at the 2023 paddle. Kym, in her sixties at the time, had only been kayaking for two years but was determined to stay active and embrace new challenges. “Finishing was the biggest feeling of accomplishment I had in decades,” her voice full of emotion.
A framed photo of Kym finishing the Islander Regatta hangs above her couch in Fishersville, Virginia. It is her daily reminder of the beauty of the Chesapeake Bay and the thrill of overcoming personal challenges.
Entering its fourth year, the Regatta continues to grow in participation and uniqueness. According to Christine, this year’s participants will celebrate their adventure with a festive Hawaiian-style shirt and a lively after-party. Following the Regatta’s activities, everyone is encouraged to attend the annual Gwynn’s Island Festival. The free and family-friendly event is held minutes from the finish line.
While enjoying the scenic beauty of Gwynn’s Island, take a moment to soak in its rich history. The island’s name originates from Hugh Gwynn, who arrived in the area in the 1600s.
According to legend, he rescued a young woman who had fallen from her canoe. The woman identified herself as Pocahontas, daughter of Chief Powhatan. In gratitude, the Chief allegedly gifted the island to Gwynn.
More reliably documented is the Battle of Cricket Hill, a significant event during the American Revolution. After fleeing Norfolk, Virginia’s appointed royal governor, Lord Dunmore, encamped on Gwynn’s Island. Commemorated at the base of the Island’s swing bridge, colonial forces drove Governor Dunmore off Gwynn’s Island and eventually out of Virginia, advancing the cause of the American Revolutionists.
Whether you come for the adventure, for the history or to reconnect with nature, you’re sure to leave with a deeper appreciation of this special corner of Virginia.
2025 Islander Regatta is Saturday, June 28, 2025, 8:00 am to 1:00 pm, Gwynn’s Island in Mathews County.
Cost is $65 per person.
