Ah, Stevensville—that charming Eastern Shore enclave on Kent Island, where the Chesapeake Bay whispers its salty secrets. The town and its dining scene have a reputation for being predictable, and it’s sometimes well deserved. Linger long enough and you’ll surely hear there’s nowhere remarkable to eat along the shore. But as it turns out, that’s all changed.
Ledo Pizza
$ | (410) 643-7979 | WEBSITE
Ledo Pizza, known for its family-friendly vibe and welcoming staff, is a refreshing change from your typical pizza spot. The menu offers solid choices like chicken boneless bites and a crisp garden salad, but the real draw here is the pizza itself—it’s consistently delicious and hits the spot. The staff is mostly friendly and handles things well, like that time they smoothly fixed a large order mix-up for a wedding party.
It’s a clean, casual place perfect for families or visitors looking for a reliable meal. Just keep in mind it can get busy, so timing your visit might help.
Tasty Toucan Ice Cream and More!
$ | (410) 657-4008 | WEBSITE
Tasty Toucan Ice Cream and More! is an ice cream shop with dozens of homemade flavors. But it’s also a family-friendly destination with not just some of the best frozen treats in Stevensville, but some of the best food in Stevensville, period. We love their warm hot fudge sundae in a sugar cone cup, the perfect grilled cheese sandwich, and one of the best ice cream flavors in town—the lemon cookie ice cream.
Stop by after school for a sweet treat, save it for a family outing with the outdoor games, or bring a big group of friends to try as many of their refreshing paleta pops as possible.
Knoxie’s Table
$$$ | (443) 222-0401 | WEBSITE
Knoxie’s Table in Stevensville is one of Maryland’s best romantic dinner spots for hand-crafted seafood dishes—we can’t stop eating the phenomenal crabcake, perfectly cooked halibut, and the fried green tomato napoleon layered with creamy corn. They don’t offer lunch service, but their savory sides, like the pepper cream corn and remade New York Strip, are a solid consolation.
Dine-in only, it will elevate your anniversary celebration before heading home to Stevensville or fuel your special occasion weekend.
Cascia Vineyards & Winery
$$ | (410) 604-2127 | WEBSITE
The best winery on Kent Island is Cascia Vineyards & Winery, a small, outstanding destination off the beaten path. The view overlooking the water from the beautiful deck is unparalleled. So are the wines and hospitality. Go for a summer afternoon, date day, or picnics with friends and dogs. The offerings include well-curated wines with thorough backgrounds, but the excellent Viognier and variety of high-quality wines remain fantastic.
Rams Head Shore House
$ | (410) 643-2466 | WEBSITE
Rams Head Shore House in Stevensville is a lively local tavern that offers an enjoyable dining experience. Order at the bar for delicious dishes like fried green tomatoes, burgers, pizza, chicken and waffles, and sandwiches. Don’t miss the Sunday night half-price burger special, which provides a great value, as well as large portions and cold drinks.
With friendly and attentive waitstaff, live music including classic rock tunes, and a highly recommended brunch, Rams Head Shore House is a must-visit spot for a wonderful dining experience.
18TWENTY Restaurant & Bar
$$ | (410) 643-5757 | WEBSITE
18TWENTY Restaurant & Bar in Stevensville presents a beautiful restored building with a comfortable, relaxing ambiance, kind and efficient service, and some well-executed American classics like mussels, crab dip, and braised short rib. Given the variety of options, it’s easy to get lost in the menu. Focus on anything from the date night offering like the delicious salmon, tender short rib, and creamy crème brûlée at this Eastern Shore restaurant.
Dress up a bit and stroll the scenic grounds after your meal to make it a special evening.
Rita’s Italian Ice & Frozen Custard
$ | (410) 604-6350 | WEBSITE
Frozen dessert shops in outlet malls are like summer blockbusters. Sure, each will offer their own flavors but you know you’re going to end up with lemon ice and vanilla custard in the end. Queenstown’s Rita’s Italian Ice & Frozen Custard seems, at first glance, to be serving the classics that get everyone in line: mango Italian ice, chocolate frozen custard, cherry gelati. But beyond the standards are well-executed seasonal specials.
We love their refreshing watermelon ice, peach custard with just the right creaminess, and swirl combinations with a little sweetness and an abundant mound of toppings.
El Jefe Mexican Kitchen & Tequila Bar
$ | (410) 604-1234 | WEBSITE
It’s fitting that El Jefe translates to “the boss,” because this Stevensville spot is the boss of Mexican food on the Eastern Shore. We especially love the fajitas, seafood soup, and Birra Quesadilla. Try to go on a Friday, the best night to enjoy the Molcajete alongside their strong tequila drinks. The steak burrito with tender meat and flavorful spices is the best-of-both-worlds for a cozy dinner while chatting with friendly staff like Brandy or grabbing satisfying takeout.
Island Pub
$ | (443) 249-3458 | WEBSITE
Island Pub in Stevensville is a lively spot for classic pub fare and strong drinks. We love anything from the grill like the juicy cheeseburger or French dip, along with the crispy, well-seasoned fries, and cold beer. The venue is light on frills but generous with fun (it’s also ideal for families).
Waterman Joe Coffee
$ | WEBSITE
Waterman Joe Coffee is a local coffee truck that delivers friendly service and delicious drinks. They offer both classic coffee with cream and sugar and specialty options like coconut milk lattes, all made with care. We can’t stop thinking about the smooth, flavorful coffee, the welcoming staff, and Miss Lisa’s personal touch. Grab a quick cup at the drive-through window for your morning commute, and save a leisurely visit for when you want to chat with the warm team.
Avanti Pizzeria, Trattoria and Market
$$ | (443) 249-3649 | WEBSITE
Avanti Pizzeria, Trattoria and Market may not catch your eye at first. It’s the hidden gem tucked inside a Stevensville strip shopping center. Once you discover it, you’ll bypass the solid-but-ordinary takeout options and make Avanti your destination for some of the best homemade gnocchi on Kent Island, along with incredible pasta and standout pizzas with excellent crust and sauce. For the evenings you’re torn between pizza and Italian comfort food, the answer can be both.
Lovepoint Deli Wine & Spirits
$ | (410) 604-2447 | WEBSITE
There are plenty of good delis in Stevensville, but few great ones: the Lovepoint Deli Wine & Spirits of the area where you’re willing to navigate the small parking lot, pay a premium price, and generally make the trip for food that’s hard to find elsewhere. Lovepoint Deli is up there with the greats. We especially like their delicious subs and macaroni salad, finished with a great selection of meats and cheeses.
Unlike places that pour all of their effort into their sandwiches, Lovepoint’s pre-made salads and amazing selection of wine, including various Cabernet Sauvignon options, are also great. Grab a sub and a bottle for the takeout trifecta.
Hardee’s
$ | (410) 643-6155 | WEBSITE
This family-friendly local spot is a must for perfectly prepared chicken and fries, a casual meal with the kids, or a quick bite after running errands. Take your meal to one of the clean booths and linger while the friendly staff, including the attentive manager, ensures everything is just right. The consistent quality and ample parking have earned this restaurant a loyal following in the community.
The Market at the Chesapeake Bay Beach Club
$ | (443) 249-5775 | WEBSITE
A good quick-service counter should not be a place for culinary complexity. A good quick-service counter is all about reliable satisfaction. The Market at the Chesapeake Bay Beach Club delivers the cream of crab soup, sandwiches, and decadent desserts of your coastal cravings. Settle into a bright, casual space that hums with the energy of beachgoers and let the efficient staff guide you to Rise Up coffee, baked goods, and those must-try pies (or grab those to go on your way to the shore).
The Kentmorr Beach Bar & Grill
$$ | (410) 643-2263 | WEBSITE
In the sea of predictable waterfront dining spots, it may be challenging to decide which one deserves your crab cake craving. In the case of Stevensville’s Kentmorr Beach Bar & Grill, the answer is in the atmosphere. Lively seating, beautiful views, kid-friendly vibes, and attentive service make Kentmorr a great dine-in option as well. For casual bites you can’t go wrong with any of the sandwiches or salads like the crab cake sandwich or chicken salad.
For dining in, go with friends for the scrumptious crabs or renowned Pain Killers at the Tiki Bar.
Cult Classic Brewing
$ | (410) 980-8097 | WEBSITE
Cult Classic Brewing is Stevensville’s all-occasion local hangout. Unlike its brewery counterparts that have defined specialties like hoppy IPAs or sour ales, Cult Classic Brewing does it all, from morning buffet offerings to family-friendly pizza nights (but let’s be real—you’re not here for the run-down exterior). Go with a big group for drinks, shareable crab dip, the large chicken sando with mango habanero sauce, UFOria NEIPA, and Amber Lager.
Stevensville Crab Shack
$ | (410) 604-2722 | WEBSITE
While Stevensville may only be a short drive from Annapolis, it feels like a world apart. But with the addition of great Chesapeake food at Stevensville Crab Shack on the Eastern Shore, the world became much smaller. Dining at Stevensville Crab Shack is like going to a Maryland friend’s backyard for a crab feast—from the friendly servers and outdoor seating to some of the area’s best crab cakes. Stop by for a casual lunch or dinner during the week.
Carini’s Pizza Subs & Pasta
$ | (410) 604-2501 | WEBSITE
Stevensville is not known for its Italian eateries, but Carini’s Pizza Subs & Pasta has been serving pizza, subs, and pasta for years. While the cozy mom-and-pop atmosphere and friendly service have not changed, the menu delivers, thanks to a dedicated kitchen. All of the food is good, but we recommend the White Pizza with bacon, tomato, spinach, and mushrooms and the Sicilian pizza, which deliver the generous portions and crispy crust you want in a reliable neighborhood spot.
