Finding Your Adventure on the Chesapeake Bay

The word Chesapeake has a magical quality. It conjures one glorious image after another: wind filling the sails of a sunlit boat, a raucous rockfish tugging at the line, a paddle dipping quietly into a winding creek, a bike leaning outside a timeless country store. 

And then, of course, the pelicans. 

Wait—pelicans? 

Yes, pelicans. That’s part of the magic of exploring the Beach to Bay Heritage Area on Maryland’s Lower Eastern Shore. You’ll find all the adventures that make the Chesapeake famous—hiking, sailing, birding, fishing, cycling, paddling, hunting—but you’ll also discover delightful surprises. Orchid hunting? A remnant of an ancient cypress swamp? Really? 

Best of all, this slice of Chesapeake heaven is wonderfully manageable. One moment you’re deep in forest or farmland, feeling worlds away. The next, you’re strolling through a charming small town—browsing boutiques, visiting museums, sampling craft beer, local spirits, or fresh seafood. 

Back to those pelicans. 

Brown pelicans are relative newcomers to the Bay, arriving in the 1980s. Today more than 1,000 nesting pairs gather in rookeries on small islands. Boat tours depart from Crisfield—long known as the “Seafood Capital of the World”—offering close (but respectful) views of swooping adults and fuzzy chicks. Bring your best camera. Try not to shake with excitement. 

Birding thrives throughout the region: shorebirds along sandy edges, herons stalking marsh shallows, songbirds filling forest canopies. The Chesapeake Bay region boasts the largest nesting population of bald eagles east of the Mississippi River. 

Waterborne adventures abound. Charter a fishing trip from Deal Island, Crisfield, or Ocean City, or rent your own boat. Paddle in the wake of centuries of maritime history—Native American dugout canoes, John Smith’s explorations, and graceful schooners, bugeyes, and skipjacks. Local watermen still harvest crabs and oysters, continuing traditions passed down through generations. 

Even land-based explorers can tap into maritime magic. The Whitehaven Ferry across the Wicomico River has operated since 1688. Nearby Green Hill Church dates to 1733. In Crisfield and Deal Island, historic skipjacks still sail, celebrated as living symbols of Chesapeake heritage. 

On the Atlantic side, Ocean City—home to the world-famous White Marlin Open—draws anglers chasing tuna, flounder, striped bass, and more. South of town, Assateague Island offers pristine beaches, hiking trails, and its famed wild ponies. 

Between Bay and beach lies an explorer’s paradise. At Pocomoke River State Park, the northernmost stands of bald cypress rise from a hauntingly beautiful swamp—the last remnant of an ancient forest that once stretched into Delaware. Paddle its tea-colored waters and you may see scarcely another soul. 

Nearby, Janes Island State Park, Deal Island Wildlife Management Area, and E.A. Vaughn Wildlife Management Area offer sweeping marsh views and exceptional birding. The Nature Conservancy’s trails along Nassawango Creek bloom with wild orchids each spring. Furnace Town preserves the story of a 19th-century ironworks village hidden in the woods. Pemberton Park pairs river trails with a stately 1741 plantation home. 

Cyclists, too, have found their haven here. Each fall, thousands ride the Sea Gull Century. Year-round, others meander along quiet, flat backroads beneath loblolly pines, watching osprey and eagles soar overhead. 

Whatever path you choose—by boat, bike, paddle, or trail—you’ll find the Chesapeake magic you’re seeking in the Beach to Bay Heritage Area. 

Except from Jim Duffy 

And yes, maybe even pelicans.