Jace Lamonica
The Chesapeake Bay has over 11,600 miles of shoreline, hiding quiet towns most tourists never see. If you need a peaceful escape, these spots are worth exploring for their stunning waterfront views. Many have fewer than 500 residents, which makes them perfect for those who crave solitude without going too far.
Rock Hall
If Rock Hall had a town motto, it might be “Come for the crabs, stay for the sunsets.” This tiny waterfront town is where watermen haul fresh catches while locals and visitors sip drinks by the docks. And if you’re into sailing, it’s a paradise because there are more boats than people on some days.
Tilghman Island
Tilghman Island is where a traffic jam means a boat waiting for the drawbridge to go up. And the locals—many of them lifelong fishermen—have stories that could fill a novel. It’s the perfect spot if you want to feel like you’ve stepped into an old fishing village where time doesn’t matter.
Onancock
Onancock may sound fancy, but this historic town is as welcoming as they come. It has just enough art galleries and charming shops to keep things interesting, but not so much that it feels touristy. It’s history, beauty, and a small-town charm all in one.
Reedville
Walking through Reedville feels like stepping into a black-and-white photograph. The town was once a hub of the fishing industry. Though things have quieted down, the charm remains just as strong. The seafood is delicious, especially if you find a spot with a water view.
Smith Island
Smith Island is for those who want to get away from it all. There are no roads connecting it to the mainland—just a ferry and a lot of open water. The locals have a distinct dialect and a unique way of life. Their most famous treat is Smith Island Cake.
Tangier Island
Tangier Island is like Smith Island’s slightly quirkier cousin. This tiny town is disappearing bit by bit due to erosion. Despite that, it’s the perfect place to slow down and enjoy the simple things in life. Like crab cakes. Lots and lots of crab cakes.
Betterton
Maryland isn’t exactly famous for its beaches, but Betterton is out to change that. This little town has a surprisingly lovely sandy beach with calm, swimmable waters and zero crowds. It was a summer hotspot in the early 1900s, but these days, it’s more of a secret retreat.
Galesville
Galesville is a tiny sailing town with just enough restaurants to keep you fed and just enough locals to make you feel welcome. The real star, though, is the water. Whether on a boat or just watching them glide past, Galesville makes you want to slow down and appreciate the simple things.
Crisfield
Crisfield is serious about crabs. This town hosts an annual crab-picking contest; locals take their seafood traditions seriously. It’s also a launch point for ferries heading to Smith Island, so if you’re in the mood for an island adventure, this is the place to start.
Sharptown
Sharptown doesn’t make many headlines, and that’s precisely why it’s unique. Sitting quietly along the Nanticoke River, it’s one of those places where life feels refreshingly simple. The river views are stunning. A historic ferry landing brings a sense of nostalgia. Locals are always welcoming and ready for a friendly chat.
