5 Hidden Maryland Islands That Feel Like a Quiet Slice of Paradise

Maryland’s Secret Islands That Feel Like a Quaint Paradise

Maryland is surrounded and shaped by water: the Atlantic Ocean, dozens of rivers and bays, plus countless creeks, lakes, and ponds. The star is the Chesapeake Bay, an estuary where fresh and salt water mix—and where many of the state’s most peaceful islands live.

Maryland has around 281 named islands, and plenty still feel like hidden escapes: calm shorelines, wildlife-rich marshes, small communities, and seafood that’s as fresh as it gets. These islands also come with real history, from Indigenous roots stretching back thousands of years to generations of Chesapeake watermen who’ve made their living crabbing, fishing, oystering, and building boats.

Assateague Island is famous, but it’s not exactly a secret anymore—so this list focuses on five lesser-known Maryland islands that still feel like a quiet paradise.

Solomons Island: Small, Scenic, and Full of Bay Charm

Solomons Island sits where the Patuxent River meets the Chesapeake Bay. It’s tiny (just over two square miles), but it delivers big on coastal vibes: boardwalk views, seafood spots, and easy outdoor adventures. It also makes a great quick getaway from Washington, D.C.

The island’s story is closely tied to the water. Fishing and oyster canning helped shape its identity, and landmarks like the unique Drum Point Lighthouse (built in the 1880s) reflect that maritime legacy. Solomons also has a notable WWII connection, and it’s home to the Chesapeake Biological Laboratory, one of the earliest publicly supported marine science labs on the East Coast.

For visitors, the waterfront boardwalk is the best starting point. Nearby, Calvert Cliffs State Park offers towering ancient cliffs, trails, beach access, and fossil hunting. The Calvert Marine Museum adds local wildlife and history, while Annmarie Sculpture Garden brings an artsy twist with outdoor installations. Boating, kayaking, and fishing round out the experience.

Smith Island: Car-Free Vibes, Wildlife, and Iconic Cake

Smith Island is a quiet Chesapeake classic: small towns, open wetlands, and a slower pace that feels like stepping back in time. It’s also home to Maryland’s official state dessert—the Smith Island Cake, known for its many layers and chocolate frosting. A stop at the Smith Island Bakery is a must if you want the real thing.

Because much of the island is nearly car-free, it’s perfect for walking and biking. On the water, kayaking and boat rides are popular, and hiring a local captain is a great way to learn about island life and traditions.

Nature lovers should explore Martin National Wildlife Refuge, a massive wetland known for birdwatching and seasonal migrations. The island is also deeply tied to crabbing culture, and seafood is a major highlight. For history, the Smith Island Cultural Center Museum offers insight into the community’s heritage and working-water traditions.

Tilghman Island: Watermen Heritage and a True Village Feel

Tilghman Island is wedged between the Chesapeake Bay and the Choptank River and is one of those places that instantly feels laid-back and local. It’s around three miles long and known for its seafood, friendliness, and maritime character.

After the Civil War, Tilghman became a key watermen community with boatbuilding and seafood businesses. Today, that history shows up in places like the Tilghman Watermen’s Museum (inside the distinctive W-shaped Lee House), plus public art such as the Tilghman Pride Mural.

Dogwood Harbor is a great spot to see working boats and learn about skipjacks—historic sailing vessels once used for oyster dredging. For outdoor fun, Knapp Narrows is ideal for kayaking, jet skis, and boat cruising. To end the day with views, head to Black Walnut Point Natural Resources Management Area for sweeping Bay scenery and birdwatching.

Kent Island: Easy Escape With Beaches, Trails, and Small-Town Energy

Kent Island is the largest island in the Chesapeake Bay—and it’s one of the easiest getaways thanks to its proximity to Annapolis. It combines coastal trails, beaches, and waterfront dining with small-town charm.

Stevensville adds personality with galleries, local shops, and community events throughout the year. You’ll also find historic buildings that reflect the island’s long story, including preserved architecture and restored local landmarks.

Down on the Kent Narrows waterfront, the Chesapeake Heritage and Visitor Center is a strong starting point for exploring local history and the Watermen’s Way Heritage Trail. Nature lovers can hit Ferry Point Nature Park for wildlife and shoreline views. For beach time, Matapeake Beach is known for views of the Bay Bridge, while Terrapin Nature Park offers trails through meadows and woods that lead to sandy shoreline.

Deal Island: Quiet Marshland, Wildlife, and Skipjack Culture

Deal Island is a rural, low-key escape on Tangier Sound, known for its wetlands, birdlife, and strong Chesapeake traditions. If you want a place that feels calm and uncrowded, this is it.

Deal Island Wildlife Management Area is the main draw for hiking, mountain biking, and spotting waterfowl and coastal birds. The surrounding waters are great for boating, paddling, and fishing. The Deal Island Historic District adds character with older churches, homes, and buildings that reflect 19th- and 20th-century island life.

If you visit around Labor Day weekend, you can catch the Skipjack Races and Island Fest—a community celebration with races, local food, and events that honor the region’s iconic workboat. For more background, the Skipjack Heritage Museum in the village of Chance dives deeper into the story of these sail-powered vessels.

How These Islands Were Chosen

To build this list, we looked at a mix of local and traveler feedback shared online, plus recommendations from travel publications and tourism sources. The focus was on islands that feel less touristy but still offer enough to do—scenery, history, food, and outdoor activities.

We also prioritized practicality: each island is within an easy trip (roughly one to three hours by car from major East Coast hubs), with additional transport only where needed for island access.