Rock Hall, MD Road Trips

Rock Hall is a town of about 1,300 people on the coast of Maryland's scenic Eastern Shore. Despite its small size, the so-called "Pearl of the Chesapeake" offers a surprising array of sights and experiences, ranging from concerts and waterfront festivals to fresh Chesapeake bay seafood.

1 The Mainstay, 5753 Main St, ☏ +1 410 639-9133. Small, intimate, informal concert venue featuring dozens of concerts every year, including jazz, classical, rock, and folk performances (updated Jun 2019) 2 Haven Point Inn and Gallery, 20748 Rock Hall Ave, ☏ +1 410 639 4184. Local inn and art gallery (updated Jun 2019)

Go kayaking on the creek or river Rent a sailboat or take sailing lessons "Pirates and Wenches" is an annual pirate-themed festival usually taking place in early or mid August 1 Eastern Neck Wildlife Refuge ("Eastern Neck"), 1730 Eastern Neck Rd (Travel southwards on MD 445), ☏ +1 410-639-7056. 7:30-30 minutes after sunset. A large (over 2000 acres) island protected by the national government. Originally designated as a refuge for migratory birds, the island has become a bird-watcher's paradise, with over 240 species of birds and 18 species of mammal visible. Hunting and fishing is allowed with a permit at certain times of year. (updated Jun 2019) 2 Shardana Sailing Charters, 20786 Rock Hall Ave, Rock Hall, Maryland 21661, ☏ +1 215-238-1365, [email protected]. 9am to 8pm. Located at Osprey Point Inn and Marina. Shardana offers an exceptional range of sailing charter experiences designed for every kind of adventurer. From relaxing half-day excursions and full-day coastal explorations to breathtaking sunset sails and immersive weekend sail getaways, each charter is thoughtfully crafted to showcase the beauty of the open water. It is a unique, private, luxury-based adventure providing Chesapeake Bay sailing trips for up to six passengers. Experience extraordinary moments aboard our private yacht. $450.00. (updated Dec 2025)

1 Waterman's Crab House, 21058 Sharp St, ☏ +1 410 639-2261. 11:30-17:00. Waterfront restaurant specializing in delicious Maryland blue crabs, though they serve other dishes as well (updated Jun 2019) 2 Ford's Seafood, 21459 Rock Hall Ave, ☏ +1 410 639-2032. 8:00-20:00. Typical Eastern Shore fare, of course including fresh blue crabs (updated Jun 2019) 3 Java Rock, 21309 E Sharp St, ☏ +1 410-639-9909. Sunday 7:00-15:00, Monday-Thursday 7:00-16:00, Friday 7:00-19:00, Saturday 7:00-17:00. Laid-back cafe and coffee shop that serves breakfast, lunch, and dinner. (updated Jun 2019)

1 Maggie's Bar (Coleman's Tavern), 21438 E Sharp St, ☏ +1 410 639-7900. 10:00-midnight. Low-key, informal hole-in-the-wall tavern (updated Jun 2019)

1 Inn at Haven Harbor, 20950 Rock Hall Ave, toll-free: +1 800-506-6697. (updated Jun 2019) 2 The Inn at Osprey Point, 20786 Rock Hall Ave, ☏ +1 410-587-0194. (updated Jun 2019)

The most common way to enter the town is by car via MD 20, which runs from Chestertown to Rockville and other villages on the Eastern Shore. Rock Hall is situated right on the water, so travelers with a boat can set it in the town's marinas.

The town is small enough that you can get around on foot with a bit of patience, though it's still much easier and quicker to use a car or bicycle. Trams can transport visitors and residents around town at the price of $1 per person. There are two such trams: one called the Osprey Flyer and another called the Blue Crab Trawler. The service runs from May to November, stopping at various tram stops throughout town, though the schedule may change when there's a holiday like the 4th of July.

Rock Hall is a very safe town. Though it is hardly an affluent place, everyone knows each other (as they do in most small towns) and crime is quite uncommon.