Savoring the Flavor of Cape Charles: Restaurateur, Jon Dempster Knows Community & Cuisine
Cape Charles is known to draw people to its uncommon and easy-going way of life. Maybe it’s because of the unique character of the place— equal parts community, celebratory atmosphere, a dash of good old nostalgia, and an infusion of the new, now and amazing.
The same can be said of the uniquely irresistible locales that make up a ‘fab four’ of Cape Charles establishments belonging to restaurateur and honorary native, Jon Dempster.
If you’ve ever had the pleasure of visiting Cape Charles, you’ve very likely enjoyed a meal, a sweet treat, or raised a glass at one of Jon’s establishments: The Shanty, Deadrise Italian Kitchen, Brown Dog Ice Cream, and E&O Pub. Each is distinctly different in taste, atmosphere and style, yet they all share common threads. In each, Jon has created a vibe and energy all its own. He, of all people, understands how important it is for folks to feel welcome when they visit.
Originally from a small town in Massachusetts, Jon’s work in the restaurant industry took him all over—Los Angeles, Seattle, Boston, and beyond. He certainly never expected to find himself in a small town called Cape Charles, Virginia. But a strange turn of the tide led him to the place he now loves calling home.
It was a dark and stormy night… Really!
“The short version of the story is that one night, the boat I was in landed in Cape Charles instead of Tortola,” says Jon. “I had never heard of Cape Charles before that night back in 2009.”
“A 6-seat golf cart painted like a taxicab picked us up in the rain and took us from the boat to what was then Kelly’s Gingernut Pub. There were five of us. It felt like the music stopped as we walked in,” Jon laughs. “By the end of the night, we had offers for places to stay, folks letting us borrow vehicles to go to the store, inviting us to join them for lunch the next day…it was incredible…and so welcoming.”
“I didn’t really choose to open a place in Cape Charles…it chose me. I ended up bartending at Kelly’s for a while, actually trying to decide how to get out of the restaurant industry.”
But there was something different in the cards for Jon. A close friend in Cape Charles encouraged Jon to open a seafood place at the Cape Charles harbor. He gathered his business partners together and in 2012, opened The Shanty right on the waterfront in Cape Charles Harbor. The Shanty is now an iconic and beloved gathering spot for locals and visitors alike, serving up fresh seafood, great views, and hospitality.
Placemaking & Taste Making
Placemaking & Taste MakingNow, The Shanty is joined by Jon’s three other establishments that are every bit as beloved by the locals and visitors who enjoy them: Deadrise Italian Kitchen, Brown Dog Ice Cream, and most recently, E & O Pub. The variety is part of the fun for Jon. Each one holds a special place in his heart, and each offers a distinct flavor and vibe.
So, which is his favorite? “It rotates! Jon laughs. “They’re all so different. I don’t have a favorite because I love them all—it’d be like choosing a favorite child.”
Jon lets his inspiration drive his involvement in each establishment. Recently, he took a trip to London, for continuing education, and to experience what pub life is like in the famous city.
“I love to travel, and my trips always inspire me to try new ideas. I’ve been in E & O every day since the trip implementing new things inspired by what I saw and experienced of London pub life.”
“As a chef, it’s fun to play with what we’re doing with the food and drink. It gets me excited every day.”
Jon’s establishments offer a lot of variety—a pub, a bespoke ice cream parlor, a hearty Italian restaurant, and the beloved Shanty. Each is as unique as Cape Charles, itself. With the established success of The Shanty, a different kind of proprietor might be tempted to open more locations in other ‘vacation towns.’ But that’s never been what Jon was about.
“I’m passionate about serving this community—that has given me so much,” he explains.
“The town has grown since I first got here. We get a lot of visitors, and we have year-round residents, too. I love seeing people come here and become a part of this community. It’s a special place…people hold the door open for each other…we know each other,” says Jon.
“There’s a certain kind of person who really enjoys it here. It’s not a bustling metropolitan area. My wife and I love to travel but we wouldn’t want to live anywhere but Cape Charles. The outdoors, nature, and the slower pace of life…we love it. It’s a true community. And you know when you go to the store for milk, it may take you a while because you’re gonna bump into ten people you know, and talk to each one,” he laughs.
Jon’s expertise for serving and delighting the public is driven by his desire to give back—whether it’s welcoming people in for a great meal, a good conversation or a raising a toast to Eastern Shore living.
Cheers to Jon Dempster and the many great ‘favorite places’ he has brought to beautiful Cape Charles. We invite you to visit and immerse yourself in the flavors, hospitality and neighborliness of this very special community.
A Brief Newcomer’s Guide to Jon’s Delicious Destinations
The Shanty
Perched on the waterfront in Cape Charles Harbor, The Shanty has been an ‘institution’ for nearly a decade and a half. Prepare for a great variety of fresh seafood and great tastes. Virginia Blue Crab Dip, local oysters, crab cakes, lobster rolls, Softshell BLT and one of the best places in town to watch the sun set.
When Jon’s boat ended up in Cape Charles completely by mistake, the local harbor master talked him into pursuing the dream.
In Jon’s own words, “The Shanty was born with a commitment to being a sustainable seafood house, prioritizing this community, and building the best restaurant possible. A lot has changed since, but the values remain the same. We strive for great hospitality, to serve local seafood whenever possible, and to give back to the community that made our dream come true.”
33 Marina Road
Cape Charles, VA
Brown Dog Ice Cream
Named after the original founder’s chocolate lab, ‘Foster,’ Brown Dog Ice Cream has become a beloved cornerstone of Cape Charles since it opened in 2012. Jon was asked by its founder to continue the Brown Dog legacy and agreed to take the helm in 2023. It’s a place where friends and family and enjoy the simple pleasure of ice cream together. And it isn’t just any ice cream—expect unforgettable flavors that surprise and delight—Brown Dog Milk Chocolate, ESCC Coffee (with local eastern shore roasted coffee infused in cream with swirls of ground espresso, Lemon Streusel, Spotted Roxie (their famous butterscotch and dark chocolate chip blend). It’s often a ‘first stop’ on vacationers’ lists when they return to Cape Charles year after year.
203 Mason Avenue
Cape Charles, VA
Deadrise Italian Kitchen
Jon and his team have put together everything you’d want in an Italian eatery at Deadrise Italian Kitchen: amazing scratch made pizzas, chicken piccata, homemade lasagna, unexpected combinations, and great cocktails and spirits to match the mood of the food. Organic pizza dough and organic marinara sauce are made fresh daily. Flavorful handmade salads—try the Insalata Mista—roasted red pepper, feta, avocado, grape tomatoes and drizzled with a tangy red wine vinaigrette—or the Prosecco Poached Pear salad for a punchy start to a great meal. And for a sweet tooth, their tiramisu, zeppole, or cannoli with chocolate chip ricotta filling do not disappoint!
425 Mason Avenue
Cape Charles
E & O
Known simply as E & O by locals and loyal return visitors, The Elephant & Octopus Public House is a pub with major atmosphere. This place is one of those ‘full circle’ stories for Jon. Named after the boat that serendipitously first brought Jon to Cape Charles, this hearty pub has been an immediate favorite from the moment it launched in April of 2025.
It opened in what was Kelly’s Gingernut Pub —the pub Jon first walked into in the ‘strange harbor’ of Cape Charles so many years ago. The pub food and spirits are as unique as Jon’s journey to Cape Charles and the hospitality is second to none. Jon is a master of the authentic and the amazing and that’s just what you’ll find at E & O.
133 Mason Avenue
Cape Charles
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