Rock Hall MARYLAND
- Located 10 miles north of the Chesapeake Bay Bridge at the entrance to the Chester River
- Founded in 1707 as Rock Hall Cross Roads, a key tourist/trade route connecting Philadelphia to Annapolis
- Venue for the lively Pirates & Wenches weekend, which takes place every August
WHAT MAKES IT UNIQUE
This small town of less than 1,500 people has an influence far beyond its size. For the land-dweller, Rock Hall is undeniably out of the way, tucked away at the end of rural MD-20, 13 miles southeast of Chestertown. And that’s exactly what makes it such a great boating destination. Rock Hall offers visitors some of the best waters for sailing, cruising, paddling and trailering. In keeping with this, the city has some of the most sophisticated marinas in the Chesapeake, many of which also offer charming shore accommodations. And for boaters, it’s not at the end of the road at all but right in the center of things, an easy trip across the bay.
There are too many beautiful marinas in Rock Hall to list. At Rock Hall Harbor, we like North Point because it’s friendly, convenient, near the Harbor Shack, and has fuel; Rock Hall Landing because its 75 deep-water floating slides are convenient to Waterman’s Crab House and downtown shopping; and Haven Harbor South, which has seen many upgrades since it was purchased by Haven Harbour, including a sandy beach with real palm trees.
On Swan Creek, we recommend Gratitude for its service and facilities as well as its “end of the road” location, as they put it; Swan Creek Marina especially for its family approach and economical mooring balls; Osprey Inn & Marina because of its pretty floating docks, gracious gardens, and well-appointed inn and restaurant; and Haven Harbour, for the professionalism of its staff, its well-stocked on-board store and its popular construction site.
ON A BOAT
The town is divided into two distinct sections: Rock Hall Harbor and Swan Creek. Both have good marinas, good places to eat and good accommodations. If you’re on a boat in choppy weather, Swan Creek offers more protection. If you want to be within walking distance of Waterman’s Crab House or any festival, Rock Hall Harbor is your choice. Whatever you do, the other is easily accessible by tram, which usually runs on weekends during boating season.
Whether you’re heading to Rock Hall Harbor or Swan Creek, find green 1 north of Love Point. This will take you to the harbor or to Swan Creek beyond. Enter the harbor breakwater, then follow the marked channel to reach the marinas that line the shore. Whichever direction you take, just be sure to stay in the channel to avoid the large shoal to the west of the breakwater. If you follow the harbor counter-clockwise you will find North Point Marina, Harbor Shack Restaurant, Bayside Landing Park and Rock Hall Landing Marina. Next is the Sharp Street boat launch, Waterman’s Crab House, Black Duck Inn, and finally Haven Harbor South.
The entrance to Swan Creek is just north of the harbor. Once inside, carefully follow the markers until you reach the marina of your choice, located in this order: Gratitude Marina, then around the tip of Deep Landing, Swan Creek Marina. Beyond is The Haven, home to Osprey Inn & Marina, Haven Harbor Marina and Spring Cove Marina.
If you cross the bay, be sure to avoid the Swan Creek Bar, going all the way south to “1” if you have a deep draft vessel. —Captain Jody Argo Schroath
Driving the route is easy; it just takes a little longer. After crossing the Chesapeake Bay Bridge on US 50, just follow the signs to Chestertown, then head east on MD-20 to Rock Hall. The same is true if you are coming from points north like Wilmington, Del. via US 301.
EXPLORE BY WATER
If you are towing your boat, you have several options for launching it near Rock Hall, including Sharp Street Public Landing and Bayside Landing
Park Boat Ramp, both at Rock Hall Harbor. You will first need to collect a county license sticker. Boating supplies can be found in marina stores as well as at West Marine and the Rock Hall Marine Railway, established in 1928.
If you prefer paddling or sailing, Chester River Kayaks is a good place to start. We suggest making the short trip to the Eastern Neck National Wildlife Refuge, 10 miles south, where you can launch your own or rent a kayak to explore this extraordinary 2,285-acre island landscape. Do you want to rent a sailboat? Set sail on a 43ft sloop with Shardana Sailing Charters or join Blue Crab Charters (2022 winner of CBM’s Best of the Bay) for five daily sails from Sharp Street.
Rock Hall is a waterman town through and through, retaining that look and feel. Start with the colorful cottages known as Rock Hall Village and the small shopping district of Main Street. Visit The Hickory Stick for cute accessories and gifts, The Bay Escape for housewares and nautical decor, and Grammy’s Goodies for hot mini donuts.
The Waterman’s Museum is a charming small town museum. Check out their retro fishing shack known as the “ark”. These small floating cabins were used by boatmen when they needed to spend the night in an area far from their home. they towed the ark behind their workboat and parked it in a convenient cove. To visit, head to the shop at Haven Harbor Marina to sign the museum keys and return them when you’re done.
Cool off at Bayside Landing Park’s public pool, open seasonally on weekends, or hit the beach at Ferry Park, which also has two gazebos, a community grill, and outdoor showers.
Think of Harbor Shack as Rock Hall’s version of Cheers, only with fresh seafood and cold beer served indoors and on the outdoor tiki deck. Haven Harbor Marina’s Passages Bar & Grill and HH South’s Admirals Club Beachside Bar have both recently been refreshed and serve frozen crushes and cocktails with a view.
The no-frills Ford’s Seafood take-out restaurant/market opens daily at 7 a.m. for breakfast, then continues through lunch and an early dinner. Enjoy steamed crabs, seafood baskets and plated dinners on site, or bring the seafood and sides back to the boat. Waterman’s Crab House has been a family classic for over 40 years, with freshly caught seafood (don’t miss the signature stuffed rockfish), seasonal crab feasts and plenty of mooring space. On weekends, top regional bands come to their waterside terrace, the largest in Kent County. The Wheelhouse, a longtime staple, has a new owner and a new name: The Blue Heron Oyster House. Come for the raw bar and shave ice, stay for a drink at the outdoor tiki bar, and look forward to the hostel rooms, which will be added in Phase 2 of the beloved property’s new life.
Start your day off right at Muskrat Alley Café, with hearty breakfasts like bacon-stuffed Belgian waffles. It’s at the Carriage House Bed & Breakfast but open to outside guests on weekends. Java Rock is a fabulous cafe that also offers tasty salads, wraps and quesadillas. Bay Wolf is an old-school staple, serving seafood but also schnitzels and bratwurst. Osprey Point Restaurant is perfect for a special occasion, even if special just means putting on long pants or a skirt. Slip reservations required for free dock and dinner.