You’ll have to wait for Labor Day weekend for Somerset County, Maryland’s biggest annual event: the National Hard Crab Derby, a festival that celebrates the oh-so-tasty Chesapeake Bay blue crab and features—you guessed it—a timed race among crabs.
But in Crisfield, the self-anointed Blue Crab Capital of the World, crab is always on the menu, as is the opportunity for a sightseeing cruise on the Chesapeake (offered primarily in the summer). Farther north and inland, you’ll find county seat Princess Anne, an appealing small town with historic homes and gardens, shops and restaurants.
The entire county, including Smith Island 12 miles offshore, sits at the tail end of the Chesapeake Country Scenic Byway, which extends north for about 400 miles along Maryland’s Eastern Shore to Chesapeake City.
The county also boasts the Somerset Trail Mix (get the app for maps, videos and more), comprising scenic trails for walking, hiking, biking or paddling (SomersetTrailMix.com).
The J. Millard Tawes Historical Museum showcases the history of Somerset County, Maryland, with a special focus on the waterman’s life and the seafood industry; photo by Blair Caldwell.
Farthest south on the Eastern Shore is Crisfield, where for generations families have made a living on the Chesapeake Bay. That history can be explored at the J. Millard Tawes Museum, perched on the water near the intersection of 9th and Spruce Streets.
Inside, you’ll find exhibits recounting Crisfield history from the late 19th century to the 20th century, when the seafood industry here was at its height. Beyond catching seafood, local residents worked at crab picking, oyster shucking and canning. So prolific was the industry back then that the bottom half of the town is actually built on oyster shells.
Decoys carved for waterfowl hunting also have pride of place in the museum, as the town was home to two of the industry’s great craftsmen: brothers Steve and Lem Ward. Ask for a special tour of the brothers’ off-site workshop, located “down neck” in ever-expanding marshland.
Kids will especially love the outdoor exhibits in a former waterman’s shanty, where they can touch different types of crabs and try out tools used by watermen, such as oyster tongs.
The marina in town is also the place for chartering a boat or catching a ferry or cruise to the two inhabited islands in the bay that can be reached only by boat: Maryland’s Smith Island and Virginia’s Tangier Island. You can also sail aboard the 1948 Helen Virginia skipjack, a type of sailboat developed in the late 19th century as an oystering workboat. Public sails depart late afternoon on select summer days.
After all that sightseeing, enjoy “dock-to-dinner-table” dining with a waterfront view on the deck of Fisherman’s Grille.
Janes Island State Park is popular with day-trippers and campers. In addition to tent and RV camp sites, there are also cabins to rent; photo by Blair Caldwell.
(CHESAPEAKE) ISLAND TIME
Drive east of Crisfield, and you’ll come to Janes Island State Park. Amenities such as campsites, rental cabins and picnic tables occupy the park’s mainland. Areas that face west often provide stunning sunset views across Daugherty Creek Canal and Janes Island toward Tangier Sound.
Janes Island itself, the island portion for which the park is named, preserves nearly 3,000 acres of saltmarsh and miles of isolated pristine beaches accessible only by boat. Thirty miles of water trails surround the island and meander along its multiple creeks. During the summer season, solo and tandem kayaks, canoes and paddleboards can be rented, and there are also a handful of adult and youth bicycles for rent, too.
Princess Anne’s historic boxwood gardens have been delighting visitors with the beauty and distinctive scent since the 1800s; photo by Blair Caldwell.
PRETTY LITTLE PRINCESS ANNE
Located 19 miles northeast of Crisfield, Princess Anne features quiet, tree-lined neighborhood streets populated with historic homes. A five-block stretch of Somerset Avenue (the town’s main street) entertains with a few restaurants, shops and the historic 1744 Washington Inn & Tavern. Dining at the tavern is special-occasion good, and the outdoor seating offers pleasant surroundings.
Across the street from the inn is Squeaky’s Café (open until 6 most nights), where the crab cakes get rave reviews. O Grace and Glory, a women’s clothing and accessories boutique, occupies the same historic building. Shop for antiques and vintage wares at Somerset Hidden Treasures and Somerset Choice Station, a shop located in an old Texaco Station that raises funds for the local historical society.
Don’t depart town without strolling through the historic 1880s boxwood garden at the corner of Somerset Avenue and Washington Street. Although the garden is privately owned, the public is welcome to visit. Look for the large active beehive in one of the trees.
Princess Anne is also home to the University of Maryland Eastern Shore, a historically Black university. Visitors can book a room at The Henson, an on-campus hotel and conference center run by the school’s Department of Hospitality and Tourism Management.
For more information on tourism in the county, go to VisitSomerset.com.