Gwynn’s Island is an island located in the Chesapeake Bay off of VA’s Middle Peninsula on the northeast side of Mathews County. It is connected by a bridge over Milford Haven.
Archaeological evidence shows that the island was inhabited as early as ten thousand years ago. In 1642, Hugh Gwynn of Jamestown purchased the island and his family were the first English settlers there. The Island served as a base for Lord Dunmore, the last royal governor of VA after the burning of Norfolk. The Battle of Cricket hill led Dunmore to leave the island by 1776.
While the history is remarkable, the view and environment of Gwynn’s Island is serene. Once you cross the bridge, you feel as if you are in a Chesapeake Bay Island paradise and your worries wash away!
Gwynn’s Island Chicken Dinner
Friday, June 28th
9am to 4pm at Gwynn’s Island Civic Center on 1996 Old Ferry Rd., Gwynn. Enjoy a delicious southern chicken dinner with all the fixings. Stay or drive through and grab to go.
Drive Thru starts at 4:30pm. Eat-in Starts at 5pm until 7pm
Tickets $12.00, Children under 10- $5. Purchase tickets at the door or at the Mathews Visitor Center in advance.
Gwynn’s Island Festival 8k & 5k
Saturday, June 29th
Start your festival the right way with a 1 mile, 5k or 8k run around Gwynn’s Island! To find out more details and register for this race, visit vttrunners.com/kukini.
8k & 5k start at 8am. 1 mile race starts at 8:10am. Raffle and awards to fillow
Event location 1995 Old Ferry Road. Packet pickup Friday night, 5-7pm at Festival Fried chicken Dinner. See details above.
Gwynn’s Island 71st Annual Festival
Last Saturday in June 29th 9am to 4pm.
Festival has a variety of handmade crafts, jewelry, wood crafts, leather, paintings, photography, ironworks. Festival will also feature live music, antique cars, Harley Davidsons, food vendors, corn hole tournament, kids zone & face painting.
Events at Gwynn’s Island Civic Center, 1996 Old Ferry Rd., Gwynn, VA 23066
