Rock Hall

So called the “Pearl of the Chesapeake,” Rock Hall has the reputation of being a world away but with worldclass amenities. True, if you were to drive by car to this mid-peninsula town, it may take quite a while to reach depending on your point of origin. But navigating by boat? Much more accessible from western shore portsof-call—and many eastern—than by driving (just 17 nautical miles from Annapolis versus 68 by car).

On the south side of town, Rock Hall Harbor is a cove protected by massive rock jetties, and is ringed by marinas and docking, as well as several fine waterfront restaurants. The town’s north facing anchorage, multiple marinas, and restaurants in and around Swan Creek/The Haven are also protected and offer access to Rock Hall Avenue, the main throughfare. Further into town, you’ll find quaint markets, gift shops, antiques, and sundries. It’s also easy to find the party in town, as Rock Hall is known for lively events and festivals, especially on summer weekends. The Mainstay is the main draw, hosting concerts and special events regularly. But perhaps the most renowned weekend of them all is the annual Pirates & Wenches Weekend—held August 11–13th—when the town transforms into a fantastical escape to the golden age of piracy and debauchery (all in good fun, mind you). For more events and all town intel, visit rockhallmd.com.

Rock Hall also serves as the “welcoming center” to the Chester River , which is a nature lover’s passage. To the town’s south is Eastern Neck Wildlife Refuge , “a 2,285-acre island providing habitat for thousands of wintering waterfowl, including the tundra swan,” states the U.S. Fish & Wildlife Service. “Eastern Neck refuge supports a wide variety of habitats including brackish marsh, natural ponds, upland forest, and grasslands. The refuge holds the designation of Important Bird Areas by the Audubon Society. Over 240 bird species visit the refuge along with small mammals and many other wildlife species.” If you have small kayaks with you, this is the place to drop them in and tour the waters around the island, go fishing, and soak in the sites.