I LIKE EARLY AMERICAN HISTORY as much as the next fellow, but there are only so many bewigged reenactors, herb-garden tours, and chewings of authentic 17th-century cinnamon sticks one can endure. After touring colonial Williamsburg, my family’s antidote was a drive up the Chesapeake Bay’s Eastern Shore. On a 280-mile circuit zigzagging up the Delmarva Peninsula from Norfolk, Virginia, to Annapolis, Maryland, we traded our tour badges for cypress swamps, sand dunes, and a passel of waterborne activities.
Can you see the light?: sunset on the Chesapeake in Maryland
Illustration by Zohar Lazar
Day 1 Norfolk, Virginia-Cape Charles
We leave behind the steel cranes and industrial grime of Norfolk and take the Chesapeake Bay Bridge-Tunnel to reach Delmarva’s slender southern end. Each of us has a task: In the way-back of the van, my daughter Sawyer, 11, wears headphones and reads colonial-themed Johnny Tremain; her sister, Riley, 8, sits in the middle seat, coloring a historical dress book in incongruous Day-Glo orange; my wife, Diane, rides shotgun, brow furrowed as she twists the map to line up with the road. I drive.
A mile onto the peninsula, at the start of our push north on U.S. 13, we stop at Sting Ray’s for the best crab cakes on the Chesapeake—golden, delicate patties that flake and steam at the push of a fork. Just another mile gets us to the Sunset Beach Resort, where we slip into double kayaks for an easy flatwater paddle past white-sand beaches and salt marshes of swaying spartina grass. Salt air and open water are delicious in contrast to the van, and I expound nonstop to my paddling mate, Riley, who falls asleep. It must be time to set the tent amid the shoreside pines of Kiptopeke State Park.
Day 2 Cape Charles-Chincoteague
We rent an outboard at teeny-tiny Wachapreague, on the Atlantic side of the peninsula. We motor out the channel to the ocean and drift past the weathered clapboard of the eerie abandoned Coast Guard station on Cedar Island. Using a chart and timing the tidal current are easy, but the expedition’s real goal, finding clams along the shore by spotting their telltale spitting, evades us. We nearly give up when Sawyer, who has been shuffling her feet ankle-deep near the low-tide line, stumbles upon a clam mother lode.
We motor back to port and drive north to a family-run campground on pony-famous Chincoteague Island. Garlic and butter—coupled with our clam stash—provide the right ending to our day at the beach.
Day 3 Chincoteague-Snow Hill, Maryland
Coastal views yield to farm and field as we head north on U.S. 13 into Maryland and then northeast on U.S. 113. We have ample time for our third floating excursion: paddling rented canoes up Maryland’s first Wild and Scenic River, the Pocomoke. The contrast with the ocean is impressive; this freshwater swamp is a bonanza of bald cypress and osprey. Turtles dive in formation from the cypress knees—plop, plop—like awkward damsels in an Esther Williams movie.
After two nights of sleeping on the ground, and corresponding doses of ibuprofen, we settle into the comfortable Snow Hill Inn for a trout dinner and real beds.
Day 4 Snow Hill-Oxford
We work our way northeast to Salisbury and take U.S. 50 to Oxford on the Chesapeake side, which consumes the morning and takes us through a series of small towns and tomato fields. Today’s car-bound games include counting cows for a cash reward, with a bonus Diane offers for each sighting of a peculiar but popular lawn decoration: a plywood cutout of a farm lady bent over and flashing her bloomers.
As we approach the shore, present-day kitsch gives way to old-English dignity. We explore the quaint town of Oxford, tucked up the Tred Avon River, via rented bikes and a trail system that takes us past grand tidewater estates hidden behind stately rows of catalpa trees. Everyone is eager for the next stop: our appointment with a chartered sailboat at the Oxford marina. Having lived aboard a boat for two and a half years, my girls know their bow from their stern, and then some. Our rented Catalina 34 sloop has two cabins and a tidy galley, which we fill with seafood and vegetables from Easton Railway Market in preparation for the morning’s departure. After Sawyer and Riley open every locker and port, they climb up onto the boom and declare it a pony. We sleep with the sound of waves lapping against the hull by our heads.
Day 5 and 6 Oxford-St. Michaels-Oxford
Sailing to St. Michaels is a four-hour trip that we spread into a day, meandering along the bay shoreline. We sail all the way to the Miles River, where we anchor for the night and are amused by the glowing blue-green water, oddly illuminated by phosphorus. In the morning, we dinghy ashore to climb the stairs of the Chesapeake Bay Maritime Museum lighthouse in St. Michaels. The museum’s interactive exhibits include a chiseled reconstruction of a wooden skipjack sailboat straight from Chesapeake oystering tradition. Across the street, bushels of bivalves and crabs arrive at the back door of The Crab Claw Restaurant and emerge from the kitchen, hot and steaming, bound for our dockside lunch table.
In the afternoon, we sail back to the Tred Avon River, which is just short of the marina. It’s our last night aboard the boat, shadowed by the trip’s end and a light drizzle. In the morning we’ll be back in the van, headed 55 miles to the Bay Bridge and Annapolis. But for now, we’re still here on a boat, with its cabin-fever-inducing small spaces that are the crucible in which families find fresh lunacy. We rally with an impromptu talent night and charades.
DAY ONE (Norfolk, VA-Cape Charles)
MILEAGE: 25.
DRIVE TIME: Half an hour.
DIRECTIONS: U.S. 13 north.
STOPS: Crab cakes at Sting Ray’s (757-331-2505) at the Cape Center in Capeville. Southeast Expeditions (877-225-2925; ) rents kayaks and leads tours.
STAY AT: Kiptopeke State Park (800-933-7275; ), 146 campsites and two boardwalks to the beach, $18 per site.
DAY TWO (Cape Charles-Chincoteague)
MILEAGE: 75.
DRIVE TIME: 2 hours.
DIRECTIONS: U.S. 13 north to Virginia 180 to Wachapreague, and then U.S. 13 north again to Virginia 175.
STOPS: Wachapreague Seaside Marina (757-787-4110) in Wachapreague rents outboard boats for $69 per day.
STAY AT: Maddox Family Campground (757-336-3111; ), $27 per site, 250 sites.
DAY THREE (Chincoteague-Snow Hill, MD)
MILEAGE: 35.
DRIVE TIME: 50 minutes.
DIRECTIONS: Virginia 175 to U.S. 13 north to U.S. 113 north.
STOPS: Pocomoke River Canoe Company (410-632-3971) rents canoes April through October. STAY AT: The Snow Hill Inn (410-632-2102): doubles, $75.
DAY FOUR (Snow Hill-Oxford)
MILEAGE: 120.
DRIVE TIME: 2.5 hours.
DIRECTIONS: Maryland 12 west to Salisbury; U.S. 50 west to Easton; Maryland 333 south to Oxford.
STOPS: Rent bikes at Mears Yacht Haven (410-226-5450). Tred Avon Yacht Sales and Charter (410-226-5000) in Oxford charters boats, with or without captain. A 34-foot sailboat for two days and three nights (one early-boarding night) costs $725. Booking in advance recommended.
DAYS FIVE AND SIX (Oxford-St. Michaels-Oxford) STOPS: Chesapeake Bay Maritime Museum (410-745-2916) in downtown St. Michaels, $7.50; lunch at The Crab Claw Restaurant (410-745-2900).