Celebrate the start of oyster season by setting sail on the Choptank River from Tilghman Island aboard the ancient, small-capacity skipjack, the Rebecca T. Ruark ($30 per person, 410-829-3976). Captain Wade Murphy will guide the ship over oyster beds and haul a batch of bivalves onto the low-slung deck using an old-school dredging rake. Afterward, head to the century-old Harrison's Chesapeake House for fried oyster sandwiches and oyster stew made with your catch. Peek inside their nearby shucking house, one of the area’s last remaining, to learn how to pry the shells open yourself.
Catch blue crabs like a local in the waters around Kent Island. Get your recreational crabbing license at the K-Mart (200 Kent Landing, Stevensville; 410-643-9600) customer service desk ($10), a couple of crab pots from Ace Hardware (300 Thompson Creek Shop Center, Stevensville; 410-643-7702) ($12–30 each), and some bait (usually chicken necks) from the Food Lion in the same plaza. Drop the traps off one of the public docks at the beach at Matapeake State Park or the coves and crannies of Crab Alley Bay and wait to see what bites. Make sure to sign a waiver to avoid trouble with the health department, and then head to the Kent Manor to have the crabs steamed for your lunch.
Circumnavigate Wye Island on a rented skiff ($31 per day) from Schnaitman’s, where the third generation of the family still facilitates recreational and sport crabbing. They’ll outfit you with crabbing and fishing gear, or just a set of oars and a map, and send you across the channel from their boat dock. Public access to the river is restricted, so the waterways aren’t crowded, and you can also walk nearby trails through old forests populated by mature hardwoods and a 290-year-old holly tree.