Ultra-fresh seafood, walkable towns, and watchable wildlife— there’s so much to love about the Eastern Shore. Here’s a seasonal sampler of “Delmarvalous” diversions.
Shop Art Galleries
Just guessing, but the Eastern Shore’s artist-per-capita ratio (as measured in painters, photographers, sculptors, fiber artists, furniture designers, printmakers, you name it) must be pretty healthy. If you’re looking for “something special” to grace the foyer, chances are you’ll find it. Begin in gallery-rich Easton and Chestertown. Home of the respected Academy Art Museum, the former hosts First Friday evening gallery walks and Plein Air-Easton, a much-anticipated annual painting competition/festival (July 14-22). The latter is home to the Chestertown Arts League (with its two galleries featuring various artworks and artists, as well as summer shows). eastonmd.org; chestertown.com.
Hug a Waterman
You’ll want to do that, figuratively speaking, after devouring fresh blue crabs at popular eateries like The Crab Claw Restaurant in St. Michaels. Honor these hard-fishing souls by visiting communities where they live, work, and preserve their heritage. Crisfield, Rock Hall, and Tilghman Island have small but noteworthy museums devoted to watermen plus events celebrating their way of life. Enjoy boat-docking, crab-picking, and crab-racing contests at Crisfield’s Hard Crab Derby (Labor Day weekend), anchor-tossing and patriotically themed workboats at Watermen’s Day (July 1) in Rock Hall, and good, old-fashioned crab eating at Tilghman’s Seafood Festival (June 23). thecrabclaw.com; crisfieldchamber.com; rockhallmd.com; tilghmanmd.com.
Be a Locavore
Foodies crave the Eastern Shore, where “farm to table” is almost within walking distance. Many restaurant menus feature not just Shore-grown fruits and veggies, but also local beef, poultry, eggs, honey, and artisanal cheeses (not to mention fresh-from-the-bay seafood). At The Tilghman Island Inn, bay crab cakes perch atop local heirloom tomatoes, and the grass-fed beef in Brooks Tavern’s BT Burger grazed 12 miles up the road from the Chestertown gathering spot. tilghmanislandinn.com; brookstavern.com.
The shore’s mostly flat, always-scenic terrain suits cyclists (kinda like a good pair of tights). One of the nicest, easiest-to-reach destinations is Queen Anne’s County, slightly over an hour’s drive from Baltimore. Tenderfoots will enjoy the Cross-Island Trail, a 6.5-mile paved route through meadows and over wetlands. It links a bayside nature preserve and boardwalk with the interactive Chesapeake Exploration Center. More experienced riders can choose from the county’s eight mapped trails covering from 18 to about 60 miles. The 22-mile Woods, Wildlife, & Water loop follows quiet country roads boasting river, creek, and critter views. parksnrec.org.
Catch Your Dinner
Spend quality time with your kids by showing them where seafood really comes from. If you’re a group, hire a charter boat (try Kent Island, Rock Hall, Tilghman Island, or Crisfield) and fish for tasty, hard-fighting species like striped bass, croaker, and flounder. The easily queasy and night anglers may find 24-hour fishing piers the ticket. Try Matapeake Pier on Kent Island for bay crabs and fish and the Bill Burton Fishing Pier (honoring the late Sun outdoors writer) on the Choptank River for striped bass, croakers, and catfish. parksnrec.org; tourdorchester.org.
Live on Island Time
It has no fancy resorts or tropical elixirs (in fact, alcohol is not sold), but for blissful disconnectedness, Smith Island makes the perfect Chesapeake getaway. Comprised of three small islands stitched together by salt marshes, this ageless fishermen’s community near Crisfield is accessible only by boat. Visit Smith Island Center to learn about local culture. Savor fresh crab cakes, and sample the island’s eponymous dessert, a gravity-defying multilayer cake. Totally smitten? Stay the night at a waterfront B&B, watch the sun set over the bay, and let the sound of workboats awaken you the next morning. visitsmithisland.com.
Below Ocean City lies a different oceanfront, a mellower place, where chilling on the beach doesn’t entail plugging a parking meter every hour. Larger, yet less heralded, than its sister seashores Cape Cod and Cape Hatteras, Assateague Island National Seashore offers the same natural diversions: swimming, beachcombing, surf fishing, camping, and hiking along trails that wind past salt marshes, pine forests, windswept dunes, and coastal bays. One of the best ways to see and photograph perhaps the island’s top attraction—the wild ponies—is by kayak. Book guided tours and rentals in Berlin, MD, and Chincoteague, VA. assateagueisland.com.
Climb a Lighthouse
The tourist’s StairMaster, lighthouses combine moderate exercise with lessons in local history. With nearly 200 steps, Assateague Lighthouse in Chincoteague National Wildlife Refuge offers a cardio workout (but plenty of rest stops). The still active, candy-cane-colored beacon has guided mariners since 1867. On the grounds of the Chesapeake Bay Maritime Museum in St. Michaels, Hooper Strait Lighthouse’s lens flashes, too, albeit unofficially. Visitors can tour all three floors of this cottagey “screwpile” lighthouse that once guarded Tangier Sound. In Lewes, DE, explore the restored 1938 lightship Overfalls, rescued from rusty oblivion to become a floating museum. assateagueisland.com; cbmm.org; overfalls.org.
Go to the Fair
Eastern Shore fairs supplement the usual (4-H animals, gigantic zucchini) with homespun entertainment (greased pig contests, cutest baby shows) and unique traditions. At the Great Pocomoke Fair, known since 1901 for harness racing, the action is professional but the wagers are friendly (Pocomoke City, Aug. 2-4). Equines also headline the Chincoteague Volunteer Fireman’s Carnival, where fireworks will ignite the island’s sky on July 7. Don’t miss the pony swim July 25, when volunteers herd a flotilla of Misty’s minions across Assateague Channel to auction. Clutch your corndog and pray no one wrecks at the Caroline-Dorchester County Fair’s self-propelled outhouse races, (Denton, Aug. 1-4). thegreatpocomokefair.org; chincoteaguechamber.com; caroline-dorchestercountyfair.org.
Visit a Winery
Given its mostly flat terrain, the Eastern Shore might not seem like optimal wine country. But grape nuts will find nearly a dozen wineries on the shore’s Chesapeake Wine Trail, including two frequent state award winners. At pastoral Bordeleau Vineyards and Winery on the banks of the Wicomico Creek in Eden (south of Salisbury), sample the varietals that won Maryland best-in-class honors last year. Ensconced in an old sewing factory on the edge of town, St. Michaels Winery offers tastings and bottles of its 17 wines, including a gold medal-winning Syrah. bordeleauwine.com; st-michaels-winery.com.
Birders flock to the Delmarva for the renowned spring and fall migrations, but summer visitors should bring their binoculars, too. Drive or cycle Blackwater National Wildlife Refuge’s Wildlife Drive to see great blue herons and egrets wading the marshes with ospreys and the occasional bald eagle overhead. Wading birds also populate impoundments at Assateague Island National Seashore, while warblers flit about the thickets. At Pickering Creek Audubon Center near Easton, sandpipers, yellowlegs, and ducks share pond space. Enjoy indoor birding at Salisbury’s Ward Museum of Wildfowl Art, a first-class facility dedicated to contemporary wildfowl art. fws.gov/blackwater; nps.gov/asis; pickeringcreek.org; wardmuseum.org.
Bring Your Boat
Every summer, power and sail boaters make their way across the bay to nautical destinations like St. Michaels and Oxford. Overnight cruisers can anchor in a sheltered cove for a cozy, lower-cost getaway or splurge and reserve a slip at a marina resort (think hot showers, swimming pools, and a break from your galley). Soak up the beauty of Swan Creek and enjoy a chef-prepared meal at Osprey Point, a Williamsburgesque inn/restaurant and marina in Rock Hall. Cruising farther? The Hyatt Regency Chesapeake Bay Resort marina—with access to a spa, golf, and gourmet dining—makes a destination unto itself. ospreypoint.com; chesapeakebay.hyatt.com.
Listen to Live Music
The Bay Bridge isn’t a sound barrier; there’s plenty of good music on the eastern side. Enjoy clubs? Visiting “westerners” can find a familiar venue at Rams Head's Kent Island outpost, Shore House in Stevensville, or discover a great local spot like Nightcat in Easton, which books nationally known indie, folk, blues, and rock performers. Don’t overlook community concert halls like The Mainstay, a folksy venue in Rock Hall, or the many outdoor concerts, including the pan-cultural Chesapeake Folk Festival (July 28) at the Chesapeake Bay Maritime Museum in St. Michaels. ramsheadtavern.com; nightcatmusic.com; mainstayrockhall.org; cbmm.org.
Discover New Cambridge
Not long ago, beach-bound travelers seeking to stretch their legs never even considered Cambridge. This once-dowdy town is downright fashionable now with a Hyatt-run luxury resort/spa, downtown art galleries, studios, gourmet and gift shops vibrant with community spirit, and restaurants praised by food critics, travel writers, and even Tom Brokaw. Taste for yourself at Jimmie & Sook’s, the locally owned (and recently relocated) seafood joint whose against-the-odds startup Brokaw chronicled; Bistro Poplar, a perennial “best of” winner among Maryland fine-dining restaurants; and the city’s new hotspot, The High Spot, a dormant eatery reborn as a gastropub. cambridgemainstreet.com.
Dance with the Stars
Sometimes you just gotta dance to the music. Outdoors. Beneath the stars. The Eastern Shore has its own tiki bars hidden along the Chesapeake waterfront. Locals know the best joints, but docked boats and potted palms signal you’re getting warm. At the end of a road, dwarfed by The Narrows Restaurant, The Big Owl is a little hoot of a bar offering water-level views, bands, and a patch of sand. Dance till you drop, and then donate your sombrero to the hat collection at Harbor Shack Waterfront Bar & Grill, a cheery Rock Hall cantina. thebigowl.com; harborshack.net.
Chestertown hosted Delmarva’s very own tea party in Colonial days. Now, this charming former port honors its anti-British-taxation past with an annual reenactment and its independent present with an array of out-of-the-ordinary shops. On South Cross Street, discover Play It Again Sam, a comfy coffeehouse/bistro favored by the Washington College crowd; Twigs & Teacups, an addictive home décor/gift/apparel shop; plus bookstores large and small. Serious collectors shouldn’t miss Chestertown Old Book Co., especially the elegant, limited-edition letterpress volumes printed by its award-winning Chester River Press. chestertown.com.
Sail on a Skipjack
Name your interest (seafood? lighthouses? nature?), and you’ll probably find a tour boat to suit your style on the Eastern Shore, especially history buffs. Skipjacks are endangered throughout the Chesapeake, but several of these classic sailboats give passengers hands-on history lessons during the summer. The Rebecca T. Ruark (built in 1886) sails daily from Tilghman Island, the H.M. Krentz (1955) has scheduled and private tours from St. Michaels, and the baby of the fleet, the Nathan of Dorchester (launched in 1994), offers public sails on weekends from Cambridge. skipjack.org; oystercatcher.com; skipjack-nathan.org.
Finally, put a cherry on top of any summer’s day by joining fellow travelers in line at the nearest ice-cream emporium. Our favorites? For nostalgia, Durding’s Store, a time-warp soda fountain in Rock Hall, where the ceiling is pressed tin, the floors are wooden, and the booths are just right for sharing a sundae with your sweetie. And for full-flavored adventure, it’s Scottish Highland Creamery, a store in Oxford, whose owner tinkers fearlessly with ingredients Ben & Jerry wouldn’t dream of. Phish Food, meet your match: Crab & Old Bay Sorbet. rockhallmd.com; scottishhighlandcreamery.com.
Watch as skilled shipwrights build or restore classic wooden skipjacks, skiffs, deadrises, and dovetails at teaching boatyards. Better yet, get a little sawdust under your fingernails by pitching in. At the Chesapeake Bay Maritime Museum’s Community Work Days (Saturdays, 10 a.m.-3 p.m.), visitors can help rebuild the skipjack Rosie Parks. The new Ruark Boatworks, part of the Richardson Maritime Museum in Cambridge, opens to the public Mondays, Wednesdays, and Fridays (9 a.m.-2 p.m.), and Saturdays, when a docent answers questions from 1-4 p.m. cbmm.org; richardsonmuseum.org.
With their dramatic water vistas and peninsular greens, these two premier golf courses have been compared to Pebble Beach. Challenge, if you dare, River Marsh Golf Club at the Hyatt Regency Chesapeake Bay resort in Cambridge, especially the 18th hole: a par-5 white-knuckler that flanks the mighty Choptank River. In Bishopville, near the ocean, the Links at Lighthouse Sound boasts scenic holes hugged by marsh grasses. The signature par-3 5th plays over the marshes onto a water-guarded green framed by the Ocean City skyline. rivermarshgolfclub.com; lighthousesound.com.