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AAA World Article

If You’re Going to Maryland’s Eastern Shore

Our top recommendations for what to do on your next Eastern Shore getaway.

By Theresa Gawlas Medoff

AAA World Article

Kayaking in the Blackwater National Wildlife Regufe
Photo courtesy of Blackwater Adventures

One reason a trip to Maryland’s Eastern Shore appeals so much is that it’s a short drive from D.C., Baltimore and Delaware—and only slightly farther from Philadelphia and Central and South Jersey—but its small towns, rural byways and watermen’s heritage make it seem a world away. For some people, an Eastern Shore getaway equates to a day or a longer stay in St. Michaels, with a mandatory trip to the highly regarded Chesapeake Bay Maritime Museum. Good choices, yes, but definitely not the only attractions that should be on your agenda.

Here are our top recommendations for what else to do on Maryland’s Eastern Shore.

Crab Claw Restaurant
Crab Claw Restaurant
Photo by Mark Sandlin

Taste the Freshness
It’s still a waterman’s world on the Eastern Shore, and that means plenty of fresh delicious crabs, oysters and rockfish to be had. Located at Navy Point in St. Michaels, The Crab Claw Restaurant specializes in—what else?—steamed Maryland blue crabs seasoned with Old Bay. You can also get your crab in soup, salad, crab cakes, as crab imperial and atop pizza.

Suicide Bridge Restaurant near Secretary was founded in 1983 by the owner of a local seafood company as a venue for serving local fish, crabs and oysters. The all-you-can-eat Friday night seafood buffet is especially popular. The restaurant’s capacity grows from mid-April through October, when visitors can sign up for a lunch or dinner cruise or a crab feast aboard one of two authentic sternwheeler riverboats plying the Choptank River.

Another long-time Eastern Shore favorite, Old Salty’s in Fishing Creek also buys its seafood from local watermen and, as with the other two restaurants, boasts great water views.


Dorchester University
of Dorchester
Photo courtesy of Dorchester Skipjack Committee, Inc.

Sail on a Skipjack
At one time, the skipjack was the working boat of the Chesapeake Bay. Built to navigate easily in shallower waters, the skipjack was introduced in the 1890s and soon became so popular that an estimated 2,000 were plying the Chesapeake at the turn of the 20th century. Today, only a couple dozen are left, most of them in museums. On the Eastern Shore, however, three still sail—and welcome aboard passengers eager for a taste of a bygone era.

Visit Assateague Island, Ocean City and all of our charming coastal towns along Maryland’s coast.

The oldest skipjack on the bay, the 1886 Rebecca T. Ruark docks at Dogwood Harbor on Tilghman’s Island. Captained by Wade H. Murphy Jr., the National Historic Landmark boat takes passengers on twice-daily two-hour sails from May to October. St. Michaels has the H.M. Krentz, helmed by Ed Farley, who’s been sailing for 60 years. From November through March, Farley uses the Krentz for oystering, but from May through October, the personable captain dons a tour guide cap and takes passengers aboard for a pleasant sail (reservations required). Over on the Choptank River in Cambridge, the Nathan of Dorchester offers two-hour public sails with oyster-dredging demos most Saturdays from May through October, with sunset cruises offered occasionally.


Eastern Maryland
in the Blackwater National Wildlife Refuge
Photo courtesy of Blackwater Adventures

Bike the Byways, or Kayak Quiet Waters

The biking on Maryland’s Eastern Shore is legendary because of the flat, quiet and scenic country roads connecting picturesque towns. The most popular route is a 29.6-mile loop that takes in Easton, St. Michaels and Oxford. Plan to stop in each town for rest and diversion. If you don’t have your own bicycle, rent one from Easton Cycle & Sport in Easton or TriCycle & Run in St. Michaels.

Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina is Maryland’s top four-diamond waterfront resort on the Eastern Shore!


Blackwater National Wildlife Refuge, with its Visitor Center just outside Cambridge, welcomes hikers, cyclists and paddlers who want to combine exercise with wildlife watching. The refuge’s forest, marsh and shallow waters provide respite to migrating shorebirds and songbirds as well as wintering waterfowl in addition to providing homes for deer, the formerly endangered Delmarva
Peninsula fox squirrel and the largest breeding population of bald eagles on the East Coast north of Florida. In addition to the paved four-mile Wildlife Drive open to cars and bicyclists (eight miles roundtrip), there are four walking trails and three water trails. Blackwater Adventures in Cambridge offers rentals as well as guided hiking, biking and kayaking tours in the refuge. 


Talbot County
Air Easton Arts Festival
Photo by Mark Sandlin

Immerse Yourself in the Arts
Wide open spaces, picturesque scenes and endless sky attract painters and other visual artists to the Eastern Shore, and there are galleries in abundance in St. Michaels, Easton and Chestertown. Just last year, Easton was named a “10 Best” Small Town for Culture by USA Today.

The town boasts the Academy Art Museum with its small permanent collection, robust exhibition schedule, classes and workshops, as well as the restored 1922 Avalon Theatre, which hosts more than 150 live music performances annually. The annual Plein Air Easton Art Festival (July 13–21 this year) is the largest and most prestigious such painting competition in the country. Also of note, the annual November Waterfowl Festival (November 8–10 in 2019) includes a variety of artists among its exhibitors, not just decoy-makers.

RiverArts Chestertown has regular exhibitions at its High Street gallery in Chestertown and hosts its own annual plein air art festival called Paint the Town each April. The art group’s Annual Studio Tour gives visitors a peek into the studios and workspaces of some 60 artists throughout Kent and Queen Anne’s Counties whose work runs the gamut from painting and photography to woodcraft and sculpture. This year’s Studio Tour will be held October 19–20 and 26–27.


This article originally appeared in the July/August 2019 edition of AAA World.

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