Most visitors come to luxuriate in the romantic history of Chestertown and its sister village, Rock Hall, but the real attraction is getting out on the water.
To get to this peninsula on Maryland’s Eastern Shore, drive across the Chesapeake Bay Bridge, and then head north past cornfields and stunning water views. Once you’ve arrived, it’s time to feast on freshly caught seafood, browse antiques shops, and stay at dreamy waterfront inns.
Two charming towns in Kent County—Chestertown and Rock Hall—are 11 minutes from Maryland’s Eastern Neck Wildlife Refuge and flanked by the Chesapeake Bay and Chester River. This peninsula was a vital port of entry in the early 18th century, and you’ll see well-preserved buildings, some predating American independence. As you stroll down Chestertown’s red brick sidewalks, grab a buttery scone at Evergrain Bread Company, or dine at the Watershed Alley, a new restaurant with a modern menu of Eastern Shore favorites.
The best way to immerse yourself in the region’s history is aboard the Schooner Sultana, a replica of a merchant vessel that sailed here between 1768 and 1772. On a two-hour voyage, passengers hear stories about Capt. John Smith, who encountered Algonquian-speaking tribal nations here in 1608. Today’s captain explains what it was like to live and travel during that time and demonstrates raising the sails and steering the tiller.
For a more deluxe cruise, board the Chester River Packet Company’s 65-foot yacht that embarks from Chestertown’s High Street Dock and includes a buffet and cash bar. There’s also Blue Crab Chesapeake Charters, with 90-minute sunset sails from Rock Hall.
Get even closer to the water by paddling your own boat. Chester River Kayak Adventures runs guided half- and full-day paddling tours, as well as sunset and moonlight tours. The outfitter rents kayaks, so you can follow the Chester River Water Trail from multiple landing sites. Whether you launch from the protected inlet at Spring Cove Marina or the open waters of Swan Creek, you’ll likely spot eagles, ospreys, and blue herons flying by.
In Rock Hall, Ferry Park Beach is a swath of sand where sunbathers can wade and swim in the bay. Grab fish tacos at Harbor Shack, keeping an eye out for watermen returning from their daily haul, and before heading home, pick up seasonal produce from Fresh Start Food & Garden.
Chestertown and Rock Hall are peaceful retreats that are far away from the hustle and bustle. With a variety of seagoing adventures, you’ll leave invigorated, rejuvenated, and ready to return for future days on the water.
EAT
Waterman’s Crab House in Rock Hall is the consummate Eastern Shore dining venue. Want amazing views? Check. Looking for freshly caught seafood? Check. Yearning for a bushel of blue crabs? They have them in season. Belly up to the picnic table or find an air-conditioned table inside, then order a basket of hush puppies with your burger or crab sandwich. It’s fun to watch the boats motor in and out of the marina here.
STAY
The views of Swan Creek from the Osprey Point Inn will soothe the soul. The elegant inn features the Osprey Point Restaurant, known for serving tender steaks and local seafood. Choose from accommodations in the Main Inn, with comfy four-poster beds inspired by the region’s colonial heritage, or The Annex on the Bay, with its porch where you can see the sun setting over the Bay Bridge. Osprey Point Inn’s amenities include a hot breakfast buffet, bikes and kayaks, and an outdoor pool with a poolside grill. The innkeepers can help you arrange golf outings and sightseeing cruises.
Feature image by Sam Shoge
This story originally ran in our May issue. For more stories like this, subscribe to our monthly magazine.
