Bring your bike (or rent one from Happy Trails Bicycle Repair, 410-643-0670) and scout wild critters along the paved Cross Island Trail, which spans six miles from Terrapin Nature Park to Kent Narrows. Browse the antiques and gift shops of historic Stevensville, or visit the Kent Island Federation of Art gallery (410-643-7424). Hit the swanky new Gravity Lounge for happy hour martinis and tasty apps (410-604-6355), before settling into a table with a view of the Bay Bridge at Hemingway’s (410-643-2722). Kent Manor Inn and Restaurant has recently revamped its menu; try the fire-roasted rack of lamb, then spend the night (410-643-5757).
November through March, go oyster dredging at sunrise with Capt. Wade Murphy on the 1886 skipjack Rebecca T. Ruark (410-829-3976). If you’d rather travel under your own steam, rent a kayak from Harris Creek Kayak (410-886-2083) and look for osprey and herons among the marsh gut. Dine on sumptuous seared rockfish and oysters in Pernod sauce at the Tilghman Island Inn (800-866-2141), and then bunk down at the Black Walnut Creek Inn (410-886-2452), spectacularly set in a wildlife preserve where the Choptank River meets the bay.
Reserve space on Capt. Otis Tyler’s Smith Island ferry for the 12-mile cruise from Crisfield (410-425-2771). Get your bearings—and learn the history of this unique place—at the Smith Island Center (410-425-3351) in Ewell, one of three villages on the archipelago. Chow down on locally caught soft-shell crabs and famous 10-layer chocolate cake at the Bayside Inn Restaurant (410-425-2771). Rent a bike or a golf cart and spend the rest of the afternoon exploring the tiny roads and getting to know the island’s 300 residents. (Chances are their last name is either Tyler, Bradshaw or Evans.) Take the late afternoon cruise back to the mainland or hop on the mail boat to Tylerton Village and spend the night at the wonderfully isolated Inn of Silent Music, surrounded on three sides by water (410-425-3541).
Visit the Virginia side of Assateague Island for more of those wild ponies and miles of undeveloped beaches, plus the annual firemen’s carnival (weekends through July) and pony swim and auction, July 28 and 29. Chincoteague National Wildlife Refuge (757-336-6122) is a 14,000-acre playground for beachcombers, hikers and bird-watchers. Slurp down some Chincoteague oysters at Steamers Seafood Restaurant (757-336-5478), and eat dessert at Muller’s Old Fashioned Ice Cream Parlour (757-336-5894), set in a circa-1875 house built by the town’s undertaker. (Ask for a ghost story along with your hot fudge sundae.) Spend the night at the Watson House (800-336-6787), a cozy Victorian inn with breakfast served on the wraparound front porch.
Browse the gift shops and galleries or get an education about the area’s seafarin’ ways at the Calvert Marine Museum (410-326-2042). Take a one-hour cruise aboard the Wm.B. Tennison, a historic Chesapeake bugeye that offers the best views of this 38-acre island located at the mouth of the Patuxent River. Hit the Lighthouse Inn (410-326-2444) for a seafood supper. And if it’s a hot summer night, a must-stop is the Tiki Bar (410-326-2424), a little slice of Margaritaville on the bay. Sleep off your hangover at the waterfront Solomons Victorian Inn (410-326-4811).