Trail News

A Haven’s Hole in the Wall

Hole in the Wall Mathews, Virginia Sign
June 29, 2019

A Restaurant Review by Jillian Lawrence

Ask any foodie about some of the best dishes they’ve ever dined on and chances are at some point, in some story, about some amazing plate of food, you’ll hear the restaurant described as a “hole in the wall.”

A tiny but mighty eatery that can hold its own against a Michelin star chef.

Heck, even Merriam-Webster defines hole-in-the-wall as a “small and often unpretentious out-of-the-way place.”

Perhaps it’s the out-of-the-way part that’s the special sauce on these small, modest spots that deliver authentic, usually locally sourced, dishes amid classic and rustic atmosphere.

Either way, hole-in-the-wall restaurants are such a driving force in the restaurant industry, you could go as far as to call them the glue that holds the food world together.

But what happens when you actually name your restaurant Hole in the Wall?

You’re telling the world that you are something special. Something worth a trip. And you better live up to it.

Hole in the Wall Waterfront Grill, a tiny, unpretentious, casual dining spot on Gwynn’s Island in Mathews County, Virginia lives up to its name in every way.

Hole in the Wall Mathews, Virginia Outside Dock and Dine

About Hole in the Wall

Hole in the Wall Mathews, Virginia Nautical ChartOpening in the summer of 2018, Hole in the Wall is located at 384 Old Ferry Road right over the Gwynn’s Island bridge in Mathews on the Middle Peninsula. It overlooks the water and its name pays homage to a waterway spot in the Chesapeake Bay right outside of Milford Haven off Gwynn’s Island, near Sandy Point, called hole in the wall.

Owners take pride in their mid-range, casual eatery where locals have the opportunity to “dock and dine.”


You can arrive at Hole in the Wall by car or boat and park in a spot or slip. Nine slips are available for boaters, and if you want, the team at Hole in the Wall will deliver food to you at the dock.

Hole in the Wall Mathews, Virginia Outdoor Dining

There’s even a boat ramp there allowing for diners to grab some grub before they launch their boat or kayak.

Getting to Hole in the Wall

Driving over the rustic swing bridge to Gwynn’s Island, Hole in the Wall is the first thing you see, snug up against the Milford Haven shore line.

Pulling into the parking lot, you’re greeted with vehicles of all shapes and sizes pulling boat trailers in and out of the water and families loading paddle boards in and out of trucks.

Stepping outside, the smell of fresh seafood and the feel of a salty breeze quickly hugs your face.

At the top of the steps to the stilted restaurant is a porch with outdoor seating. Inside the front door is a room of happy people, hostess with a smile and a bartender offering to get you a soda as you wait for a table to open up.

Hole in the Wall Indoor Dining Mathews, Virginia

No matter what table you find yourself on – one on the patio outside or one inside – the view is equally breathtaking.

You have to believe it was designed that way so that even on a rainy day, or when all the tables outside are taken, you can still enjoy the view of the water and the Chesapeake Bay thanks to the building’s high ceilings and walls of windows.

Eating at Hole in the Wall

So what’s on the menu?

Hole in the Wall Mathews, Virginia Food

Like lobster rolls? How about a lobster roll re-imagined for Chesapeake Bay lovers? At Hole in the Wall, they create a perfect roll combining lobster and the Chesapeake Bay’s beloved blue crab, sourced from Sea Farms right down the road from the restaurant. Talk about bay to plate.

Hole in the Wall Lobster Roll Blue Crab Mathews, Virginia

There’s also a classic BLT burger (and an entire burger section on the menu), combining two summer favorites. This savory burger includes a tomato jam, Swiss cheese, and crispy bacon combination that gives it a sharp and flavorful bite. The burger is so juicy, be sure to get extra napkins.

Hole in the Wall Mathews, Virginia Clam Strips

Then there’s the fried clam strips – and many other fried seafood options presented in baskets. Crispy and light. Not too much breading, allowing the seafood to shine. And just like the crab in the lobster roll, the clams are sourced locally, making the dish even sweeter knowing each are caught by someone nearby and fresh from the sea.

Rainbow trout is also on the menu. While you won’t find this fish locally in Middle Peninsula waters, it is a hit at Hole in the Wall as a fish special. Mild in flavor, yet crispy with a gentle texture in every bite, makes this classic “fish and chips” meal one that does not disappoint.

If it’s oysters you like, there’s plenty of options to satisfy your cravings. Sourced locally from Williams Wharf Oyster Company, order them steamed or raw, by the dozen or half dozen.

Hole in the Wall Mathews, Virginia DessertWant tacos? They have those, too. Fish tacos. Shrimp tacos. And a special taco of the week.

Don’t leave without at least checking out the dessert menu. Dark chocolate torte with caramel sauce and whipped cream. Mixed berry bread pudding with cream cheese icing. Oh, my!

Come hungry. Enjoy the view. Leave full and happy.

Want to make your own trip to Hole in the Wall? Learn more about this Mathews County eatery at Open for lunch and dinner starting at 11:30 a.m. Closed Wednesdays.