Tour The Shore

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.

Go Cycling

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.

Explore Assateague

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.

Go Birding

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.

Browse Chestertown

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.

Just Chill

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.

Learn Boatbuilding

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.

Tee Off

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.