Discover the Best of Kent Island: Where to Eat, Drink & Explore
From waterfront seafood and Chesapeake Bay sunsets to locally loved coffee shops and scenic trails, Kent Island offers plenty to explore. Whether you are planning a romantic dinner, a relaxing weekend, or a day by the water, here are some of the best places to eat, sip, shop, and explore.
🍽️ Best Restaurants on Kent Island
Fine Dining
18TWENTY Restaurant & Bar
Located at Kent Island Resort, 18TWENTY offers a refined farm to table dining experience inspired by the Chesapeake Bay.
Perfect for date nights, brunch, and sunset dinners, the menu features fresh seafood, steaks, seasonal dishes, and handcrafted cocktails.
Best For: Date night, brunch, special occasions, sunset dining
📍 500 Kent Manor Dr, Stevensville, MD 21666
🌐 Visit 18TWENTY Restaurant & Bar
Knoxie's Table
Enjoy upscale American cuisine in a beautiful waterfront setting. Knoxie's Table is especially popular for a relaxing meal with a view.
Best For: Waterfront dining, date nights, special occasions
📍 180 Pier 1 Rd, Stevensville, MD 21666
🦀 Seafood Favorites
Bridges Restaurant
Beautiful waterfront views meet classic Chesapeake flavors at Bridges Restaurant. Enjoy seafood favorites while overlooking Kent Narrows.
Outdoor seating makes this an especially great choice when the weather is beautiful.
Best For: Waterfront seafood, outdoor dining, sunset views
📍 321 Wells Cove Rd, Grasonville, MD 21638
Harris Crab House
For a true Maryland crab experience, Harris Crab House is a must visit. Dig into Maryland blue crabs, crab soup, steamed seafood, and Eastern Shore classics.
Best For: Maryland blue crabs, families, authentic Eastern Shore dining
📍 433 Kent Narrow Way N, Grasonville, MD 21638
Dock House
Fresh seafood, casual waterfront dining, and beautiful sunset views make Dock House an easy choice for a laid back meal near the water.
Best For: Casual seafood, drinks, sunset dining
📍 110 Piney Narrows Rd, Chester, MD 21619
☕ Coffee & Sweet Treats
Dessert First Dockside Coffee & Dessert Bar
Coffee, homemade desserts, ice cream, and dockside seating make Dessert First the perfect stop when you are craving something sweet.
Best For: Desserts, coffee, ice cream, waterfront breaks
📍 433 Kent Narrows Way N, Grasonville, MD 21638
Waterman Joe Coffee
A local favorite for quality coffee and breakfast. Stop in before exploring Kent Island or grab something to enjoy on the go.
Best For: Morning coffee, breakfast, quick bites
📍 415 Romancoke Rd, Stevensville, MD 21666
ground work @ the corner
A cozy neighborhood spot serving specialty coffee and pastries in a welcoming atmosphere.
Best For: Specialty coffee, pastries, relaxing mornings
📍 111 Cockey Ln, Stevensville, MD 21666
🌐 Visit ground work @ the corner
🍕 Casual Dining
Amalfi Coast Italian + Wine Bar
Enjoy Italian favorites paired with a great wine selection in a welcoming Kent Island setting.
📍 401 Love Point Rd, Stevensville, MD 21666
🌐 Visit Amalfi Coast Italian + Wine Bar
Frix's Fire Grill
A casual choice for flavorful food and an easygoing dining experience.
📍 1533 Postal Rd, Chester, MD 21619
Big Owl's Tiki Bar
A fun waterfront destination with an especially lively atmosphere during the warmer months.
📍 3015 Kent Narrow Way S, Grasonville, MD 21638
Rams Head Shore House
A laid back local spot for food, drinks, and casual dining.
📍 800 Main St, Stevensville, MD 21666
🛍️ Things to See & Do Around Kent Island
There is more to Kent Island than great food. Make time to explore the waterfront, trails, beaches, shopping, and local history.
Kent Narrows Waterfront
Explore marinas, seafood restaurants, waterfront destinations, and scenic surroundings while taking in the Chesapeake atmosphere.
This is an especially beautiful area to explore around sunset.
Terrapin Nature Park
Enjoy beach access, walking trails, natural scenery, and beautiful views of the Chesapeake Bay Bridge.
Don't Miss: Sunset by the water.
📍 191 Log Canoe Cir, Stevensville, MD 21666
🌐 Explore Terrapin Nature Park
Cross Island Trail
Perfect for biking, walking, or simply slowing down and enjoying the scenery.
The trail crosses Kent Island and provides a great way to experience the area's natural surroundings.
Chesapeake Heritage & Visitor Center
Discover more about the area's history, heritage, and culture while enjoying beautiful Kent Narrows waterfront surroundings.
📍 425 Piney Narrows Rd, Chester, MD 21619
🌐 Visit Chesapeake Heritage & Visitor Center
Queenstown Premium Outlets
Looking to fit some shopping into your trip? Queenstown Premium Outlets is a short drive from Kent Island and offers a wide selection of outlet stores.
📍 441 Outlet Center Dr, Queenstown, MD 21658
🌐 Visit Queenstown Premium Outlets
⭐ Our Top 5 Kent Island Picks
1. 🍽️ 18TWENTY Restaurant & Bar
Best overall dining experience
2. 🦀 Bridges Restaurant
Best waterfront seafood
3. 🦀 Harris Crab House
Best Maryland crab feast
4. ☕ Dessert First Dockside Coffee & Dessert Bar
Best desserts and coffee
5. 🌅 Terrapin Nature Park
Best sunset spot
🌊 Planning a Weekend on Kent Island?
Turn your visit into a Chesapeake Bay getaway with a full weekend of great food, waterfront views, local attractions, and hidden gems.
Explore our 2 Day Kent Island Itinerary for recommendations on where to have breakfast, lunch, and dinner, plus sunset spots, wineries, scenic stops, and local favorites.
