7 Off-The-Grid Chesapeake Bay Towns To Visit In 2025

Tired of boardwalk crowds and polished waterfronts? The 200-plus miles of Chesapeake Bay thread through Maryland and Virginia, supplied by the Susquehanna, Potomac, and a score of tidal rivers that once served steamboats, skipjacks, and canneries. Shipbuilding, oyster dredging, and commerce from this estuary built hundreds of small towns along its salty shores during the 1700s and 1800s. Many of those towns are still quiet, bypassed by travelers in favor of more prominent names like Annapolis or Virginia Beach. Still, for travelers adventurous enough to go off the beaten track, these seven towns have something unique to share: ferry slips, old crab houses, forgotten shores, and a slower beat that still harmonizes with the tide's ebb.

North Beach, Maryland

North Beach feels like a throwback to classic summer towns, the kind you see in old beach movies: all boardwalks, fishing piers, and kids running barefoot across the sand. Follow the wooden planks of the North Beach Boardwalk, a half-mile stroll past fishing piers, quirky statues, and benches, to watch a sunrise or cast a line lazily into the bay. A short walk across the sand, Wetlands Overlook Park brings you face to face with herons, turtles, and marsh grasses bobbing in the wind.

Stop by the Bayside History Museum to learn about Chesapeake legends and shipwrecks, then get your fill of fresh seafood, homemade pies, and everything you never knew you needed at the North Beach Farmers Market. When evening falls, grab a blanket and get cozy for Movies on the Beach, where free movies run by moonlight along waves crashing mere feet from your blanket.

Cambridge, Maryland

Sitting atop the broad Choptank River, Cambridge is a historic city in Maryland dating back to 1684. Grand 1700s and 1800s homes along its prestigious High Street impressed even writer James Michener, who drew from it when writing his novel "Chesapeake." Stroll along Long Wharf Park's waterfront, where sailboats bob in view and history hangs in the air. Visit the Harriet Tubman Museum & Educational Center to get a poignant glimpse into the life of the Underground Railroad’s most legendary conductor, or learn about boatbuilding history at the Richardson Maritime Museum.

For an extended sojourn into history, drive along the Harriet Tubman Byway, a 125-mile route marked by historic sites. If you’re traveling during spring, don’t miss Cambridge Main Street's Spring Fling, a celebration of food, music, and community spirit.

Cape Charles, Virginia

There’s nothing flashy about Cape Charles, but this small bay town on Virginia’s Eastern Shore draws in travelers who want quiet streets, seafood, and water views. Cape Charles Beach has a peaceful, pedestrian-friendly coastline, public art, and safe swimming. History enthusiasts visit the Cape Charles Museum and Welcome Center, while nature lovers explore the Cape Charles Natural Area Preserve to see its dunes. Immediately outside of town, one of the area’s most dramatic drives connects the Eastern Shore to the mainland through the enormous Chesapeake Bay Bridge-Tunnel.

Cape Charles springs to life every summer during the quirky Clam Slam Festival, which boasts a boat docking contest, seafood cookouts, and family games. The Shanty brings steamed shrimp and cold beverages dockside on the water for a casual dinner.

St. Michaels, Maryland

St. Michaels keeps its harbor town spirit alive, from its shipbuilding past to its festival-packed present. Stop by the Chesapeake Bay Maritime Museum, where you can board historic vessels and observe shipbuilders in action. Hop aboard a guided Patriot Cruise, which makes its way past mansions, crab houses, and century-old lighthouses that line the shore. Stop by stores like American/Holiday, or shop local artwork at Creative Xpressions, along thriving Talbot Street.

Take a breath of fresh air by walking through Muskrat Park, a tranquil park along the harbor ideal for a picnic or sunset watching. Visit during special town-wide celebrations such as ChocolateFest in March, WineFest in April, and OysterFest in late October.

Onancock, Virginia

This town doesn’t just sit along the Eastern Shore. It’s been turning heads since the 1600s. Captain John Smith aptly declared it “the Gem of the Eastern Shore,” and centuries later, it still meets the description. Relive history at Ker Place, an 18th-century mansion filled with artifacts and displays of local history. Take a ferry ride to Tangier Island, where crab culture, old-time accents, and weathered boats reflect island life.

Stop downtown at Red Queen Gallery, where paintings of ocean themes and ceramics capture the region’s best creative spirit. Next, try out the Oyster Odyssey scavenger hunt, a lively walking tour filled with quirky details.

Betterton, Maryland

Few towns feel as quietly remote as Betterton, a small Kent County village set right along the Bay. Beachgoers gather at Betterton Beach, a broad, sandy beach ideal for low-key afternoons. The Betterton Heritage Museum, inside a restored church, preserves the town's heritage of steamboat days. Small-town charm comes alive at events like the Betterton Day and Kent County Waterman’s Day, both lively affairs celebrating Chesapeake Bay traditions.

Directly across from Betterton Community Park, Marzella’s By the Bay offers Philly cheesesteaks and pizza in a relaxed atmosphere. Its Philadelphia restaurant owners, in retirement, provide a taste of city living in this peaceful Kent County hamlet. The Betterton Public Landing also has convenient access for crabbing, fishing, or simply viewing open water.

Irvington, Virginia

It’s easy to miss Irvington on the map, but this quiet bay town packs in more than you’d expect. History buffs visit the Steamboat Era Museum, where ship replicas, photographs, and memorabilia of the town’s seafaring heritage abound. Near town, the Historic Christ Church & Museum, constructed in the 1730s, impresses through its unique Georgian style and beautifully preserved interior. The Tides Inn, Irvington’s most popular attraction, provides boat rentals, spa services, and views of Carter’s Creek.

Locals and tourists commingle at the Irvington Farmers Market, where you can get crab cakes, locally sourced honey, and hand-painted pottery. Wine enthusiasts pass through The Dog and Oyster Micro-Vineyard, where bottles are paired with salty oysters. Small stores and studios are adding to the low-key appeal.

Chesapeake Towns That Time Skipped

These towns don’t draw crowds, and that’s precisely what makes them special. Each town has retained its connection to the Bay through working piers, ferry crossings, secluded beaches, and crab houses that people still depend on. You won’t need a packed schedule. All you need is time and a curious mind. The tide still dictates the day in most of these towns, and a gull’s cry or a boat engine humming in the distance might be the only loud sound you’ll hear. These are the towns to see if you’re the type of traveler who prefers small diners to chain eateries, and marshland roads over boardwalk crowds. They won’t remain forgotten forever, but they are still wide open for now.