Chesapeake Bay’s Outer Limits: Exploring Maryland’s Delmarva Peninsula

Smith Island on the eastern shore of Maryland.
Smith Island on the eastern shore of Maryland.Betty Wiley / Getty Images

When winds hammer out of the southeast, no captains in Crisfield, Maryland, want to fight the five-foot whitecaps that churn Chesapeake Bay. Gusts hit 50 mph, boats stay put, and the bar inside VFW Post 8274 expands its clientele. This sort of boozy detour is typical of a trek across the Delmarva Peninsula, a tri-state teardrop of muck, black rivers, and spooky forests that stretches almost 200 miles from Delaware, through Maryland, to Virginia. The 80-mile trip along the bike paths and rivers that connect the region’s historic inns and crab houses unrolls through pristine country.



Cross the Bay Bridge from Annapolis to the Eastern Shore, exit the highway, and you enter a land where “heaven and earth never agreed better,” as Chesapeake explorer Captain John Smith wrote in 1612. Lonely roads roll through stands of sweet gum trees, over wooden bridges, and into colonial towns in which locals wrap their words in a Tidewater twang. Kayakers slip along the nation’s northernmost reaches of bald cypress swamp. There are fish, too, and plenty of men looking for them.

The best place to start is Assateague, a 37-mile-long barrier island with wild ponies and Sitka deer. This lovely wilderness sits just south of Ocean City, a strip of T-shirt shops and crowded beaches popular with “Baltimorons,” as some locals call them. Further down the coast lies the longest span of undeveloped beach on the entire East Coast. Adventurers can camp on the side of a dune dusted in the silver light of a full moon and fall asleep to the sound of waves bouncing off the continent.

From the beach, it is a 40-mile ride to Snow Hill, a sleepy port on the Pocomoke River settled in 1642, along roads closely monitored by blue grosbeaks, indigo buntings, and dunlins. Lucky pedalers can sometimes spy fox pups playing in the fields. Only a handful of cars seem to hug this asphalt. Stay the night at the River House Inn, a gothic bed and breakfast perched in the willows that offers the same rich quiet as the marshes further from town.

Wooden walkway to illuminated treehouse

The Best Treehouse Hotels of Summer 2018

Read article

“I don’t want to say it’s the East’s last sacred place, but it kind of is,” says Beth Lefebvre, a spokeswoman for the Chesapeake Bay Foundation, of the area. Oysters were once so abundant here that they filtered every drop in the bay in less than a week, keeping it so clear that Captain Smith could see 60 feet down. Now manure and fertilizers wash into the waters, creating algae blooms. Still, the land itself is well preserved.

Pedalers can head west toward Crisfield and hop the boat out to Tylerton, Smith Island’s minuscule main drag, if the weather stays calm. Along the way to the shore, gourmands gorge themselves on crabs at The Red Roost and down pitchers of Delaware-brewed Dogfish Head. Those who don’t succumb to the inertia of a full stomach find more crab on the island, where kayakers can launch themselves into protected waters in search of shipwrecks.

Bob Leef, a local kayaker and fisherman, says the best place to find buried treasure is a marshy spot not too far from Tylerton that offers explorers the chance to paddle into the half-submerged ships once captained by picaroons like Marmaduke Mister – when the tide is right anyway.

“There are a lot of places around here that will blow you away,” Leef says. “You just need to know how to look for them.” In a land as overlooked as Delmarva, that’s the key to everything.

More information: Delmarva Low Impact Tourism Experiences (otherwise known as DLITE) sells excellent biking maps for DIY explorers and the folks at River House Inn, where rooms run from $160, can help point you in the right direction. The ferry leaves Crisfield for Smith Island twice a day, at 12:30 p.m. and 5 p.m.

For access to exclusive gear videos, celebrity interviews, and more, subscribe on YouTube!