Steeped in Chesapeake Bay-spawned flora and fauna, Maryland’s Eastern Shore is our homegrown playland, residing on a peninsula of intertwined waterways accessible from the Atlantic Ocean and shared by three states. The region’s unique geography served as a gateway for significant events that shaped our country — colonization and three democracy-defining wars — and hosted a diverse array of pioneering personalities, including Harriet Tubman and Capt. John Smith.
Today, the once-sleepy towns along the Shore are exciting enclaves of active-adventure pursuits, historic landmarks, sophisticated arts scenes and progressive cuisine incorporating indigenous ingredients. While practically every sector on the Shore has something to offer, we’ll get you started with our favorites.
Queen Anne’s County
Just over the Bay Bridge, circa 1631 Kent Island (kentnarrowsmd.com/) — the third-oldest English settlement on the continent — is a bastion of hiking, biking and beaches. Sandy shores along the 276-acre Terrapin Nature Park provide unobstructed bridge vistas. Also check out historic Stevensville’s vibey arts and entertainment district.
Kayak alongside otters, terrapins and coastal birds on the Chesapeake Bay Environmental Center’s (bayrestoration.org/) Marshy Creek tour. The 510-acre campus features native woodlands, tidal marshes and trails.
Chesapeake City (chesapeakecity.com/), Maryland’s only town on a commercial canal, is a scenic community of galleries, antique shops, waterfront eateries and summertime celebrations. Its C&D Canal Museum exhibits its history and archeological finds.
As a thriving colonist seaport, Chestertown (townofchestertown.com/visitors/) hosted its own “tea party” rebellion against the British in 1774. Today, folks re-enact the revolt at the Colonial Tea Party Festival (May 25-27), sail the Chester River aboard the Sultana, a replica 1770s-era British schooner, and stroll brick sidewalks fronting High Street’s boutiques and galleries.
Boaters dock at postcard-perfect Rock Hall to crack crabs and rock out to live music at outdoor eateries, explore marine artifacts at Waterman’s Museum and whoop it up at quirky festivals, such as July’s Log Canoe Regatta and August’s Pirates and Wenches Fantasy Weekend — sing-alongs, rum tastings, and bounty-scavenger hunts.
Easton (discovereaston.com/) packs sophisticated city venues into its charming town: Academy Art Museum exhibits prominent national and local artists, charging just $3 admission. The art-deco Avalon Theatre premieres music performances. Downtown is a bastion of tony antique shops, galleries and inventive restaurants.
Encounter northern mockingbirds, indigo buntings, and yellow-rumped warblers at Pickering Creek Audubon Center (pickeringcreek.audubon.org/), a 400-acre sanctuary of trails teeming with coastal wildlife habitats.
St. Michaels’ (stmichaelsmd.org/) intoxicating spirit lies beyond its cache of stylish shops and inns. Its burgeoning craft-beverage movement features Eastern Shore Brewing, Lyon Distilling and St. Michaels Winery. But before you imbibe, visit Chesapeake Bay Maritime Museum, exhibiting bay history, vessels and culture.
Three-mile-long Tilghman Island (tilghmanisland.com/) is revered for its rustic milieu, multi-generational watermen and Phillips Wharf Environment Center’s touchy-feely nature experiences. Reopened: Lee House, a “W”-shaped home circa 1890 at Tilghman Waterman’s Museum. Stay overnight at Wylder Hotel, a new lifestyle resort with a saltwater pool and resident fishermen organizing charters.
Watch indigenous grain and seeds being ground into barley, grits and flour, using late 19th-century equipment. The circa 1682 Wye Grist Mill’s (oldwyemill.org/) roster of prominent clients includes Washington’s Continental Army of the American Revolution.
Residing in Tuckahoe State Park, Adkins Arboretum (AdkinsArboretum.org) offers 400 acres of native gardens, interpretive walking paths and wetlands. Afterwards, visit the quirky Telephone Exchange Museum in Ridgely. (carolinehistory.org/places/ridgely-telephone-exchange/)
Daytrip to Denton’s vibrant Artsway (carolinearts.org/denton-artsway/), a 90-acre cultural district of galleries, boutiques, Fiber Arts Center (famous for their quilt collection), The Foundry (exhibiting local artists) and Museum of Rural Life.
Little-known Federalsburg’s (visitcaroline.org/our-towns/federalsburg/) Historical Society exhibits canneries, factories (including a mother-of-pearl button machine), early farm equipment and transport that made Caroline County’s southernmost town a colonial-era hub of agriculture and industry. Before leaving town, sample Fed Brew’s Kombucha.
Harriet Tubman Park and Byway (harriettubmanbyway.org/) is an enthralling 125-mile route through Dorchester and Caroline counties, showcasing 36 sites significant to slavery and escape, including Tubman’s birthplace, the place she escaped slavery and where she led others to freedom.
Bordering the Choptank River, Cambridge (downtowncambridge.org/discover-downtown/), was an important depot on The Underground Railroad. Take the Historic Walking Tour (Saturdays) of Cambridge’s landmarks, including Harriet Tubman Organization Museum. Explore downtown’s artsy shops, haunted spots and the world’s oldest crabhouse, J.M.Clayton.
Hike and paddle through unadulterated trails and tidal marshes amid hundreds of coastal bird species at the 27,000-acre estuarine waterfowl sanctuary, Blackwater Wildlife Refuge (fws.gov/refuge/Blackwater/).
Discovered by Capt. John Smith, Smith Island (visitsmithisland.com/) is Maryland's only inhabited offshore island; present-day natives still speak “Tidewater English.” Watch watermen’s wives pick and pack crab meat at Tylerton’s Crab Meat Coop. Sample some at Drum Point Market, Tylerton’s only restaurant. Ferry to Ewell for island history at Smith Island Cultural Center and for the authentic 10-layer cake at Smith Island Baking Company.
It might sound kitschy, but Somerset County crab enthusiasts revere the Governor’s Cup Crab Race, picking competitions, Miss Crustacean Beauty Pageant and Watermen’s NASCAR (boat docking competition) at Crisfield’s National Hard Crab Derby (nationalhardcrabderby.com) on Labor Day weekend.
Boasting a unique manifold of downtown sights — The Ward Museum of Wildfowl Art, Eastern Shore Baseball Hall of Fame, craft breweries and a university — Salisbury (salisbury.md) is the 2018-2020 home of the National Folk Festival, the oldest multicultural traditional arts celebration in the U.S.
A country store, a one-room schoolhouse, a doctor’s office and a train depot are among 10 historic buildings demonstrating early-American culture in Mardela Springs, at Adkins Historical and Museum Complex (adkinsmuseum.com/tours). Tours are free but must be booked in advance.
After Berlin (berlinmainstreet.com/) was named America’s Coolest Small Town by Budget Traveler Magazine in 2014, the secret was out. Beyond avant-garde galleries, innovative theater and phenomenal local fare, there’s the cooler-than-cool Fiddler’s Convention, hilarious bathtub races and summertime festivals.
Costumed interpreters re-enact colonial life in craftsman studios, in pristinely preserved 19th-century buildings and at the Nassawango Iron Furnace, here at Furnace Town’s Living Heritage Museum (furnacetown.org/).
In Pocomoke City, aka Eastern Shore’s Friendliest Town (downtownpocomoke.com/), tour the African-American Sturgis One Room School, the immersive Delmarva Discovery Center living museum, and catch a performance at the historic 720-seat Mar-Va Theater.
Follow Snow Hill’s (snowhillmd.com/visitHere.cfm) scenic self-guided walking-tour across a footbridge over Pocomoke River, to historic churches, homes, the Julia A. Purnell Museum and the Worcester County Courthouse (which once doubled as a slave market).
Just beyond Assateague, NASA Wallops Flight Facility (nasa.gov/centers/wallops/visitorcenter) exhibits current missions, orbital rockets and aeronautics, and hosts astronomy nights and public viewings of rocket launches.