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Though modest in size — roughly three miles long and less than a mile wide — the island offers spectacular views, peaceful seaside living, and a strong connection to the bay’s natural rhythms. 

Gwynns Island Cricket Hill AirBNB (1).jpg

Key Location

First stop after the Swing Bridge

With 360 Island Views, Cricket Hill House is a warm welcome when crossing the sigature swing bridge of Gwynn's Island, Mathews Virginia. 

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Milford Haven, the channel separating the island from the mainland, is not just a stunning tidal waterway — it’s also a world-class oyster region. Coastal growers raise oysters in these brackish waters, a legacy of centuries of shellfish culture.

Aerial Gwynn's Island Cricket Hill House 2
Aerial Mildford Haven Cricket Hill House
Aerial Gwynn's Island Cricket Hill House
Gwynn's Island aerial shot
Hole in the Wall Gwynns Island

Hole in the Wall

Just a stone's throw from our doorstep

One of Mathews' favorite waterfront seafood restaurants is a few steps away from Cricket Hill Houses. Enjoy a great menu of fresh fish, shrimp, seafod specials, juicy burgers, and an imaginative cocktail menu. The restaurant has outdoor seating and often features live music in the off season. You definitely might make a few trips during your stay - and we wouldn't bat an eye! 

The Hatchery Eatery

A full circle aquaculture experience

This hidden gem is an oyster-lovers dream, but it's not what you might envision. The Hatchery is a a waterfront food truck that offers a raw and roasted oyster bar, fried oysters served via tacos, banh mis and po'boys, and pork dishes. They have a craft beverage bar, and they offer tours o their seed hatchery facility on Fridays in the summer. Or you can hop on a boat charter and take a cruise on the Milford to visit an oyster farm up close! 

The Hatchery Oyster Eatery
Gwynns Island Museum

Gwynn's Island Museum

Fridays and Saturdays, April - October

The island has been inhabited for thousands of years — from indigenous peoples, early colonial settlement (since at least the 1600s), and Revolutionary War activity — to a modern fishing and leisure community. So the small island community created its own museum to honor its history.  Drop by to see fascinating artifacts, learn about the Battle of Cricket Hill, the story of the Mathews Men serving in World War II, or perhaps the Cinmar Blade, as 23,000 artifact that was once discovered in a dredge hall.

Annual Island Events

Stay close by to these Island events

The Gwynn's Island Festival, a decades-long tradition where locals and visitors gather to enjoy live music, local vendors including crafts, food and art, kids activities, and more! The festival takes place the last weekend in June.

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The Islander Regatta, also the last weekend in June, is a 9 mile paddle that circumnavigate the entire Island! Stay walking distance from the event and join a sea of over a hundred kayakers and paddleboarders down the Haven, up the Chesapeake Bay, and around the Piankatank River.

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The Raw Bar Run 5K (April), National Oyster Day (August) and Oyster Equinox (September) are two new annual events thrown by The Hatchery Eatery to celebrate community and aquaculture!  

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Islander Regatta Event Mathews Outdoor Club
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