The Eastern Shore's "Pearl of the Chesapeake", Rock Hall offers something for everyone this summer.

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Sunrise on Swan Creek. Photo by Craig Ligibel

Swashbuckling pirates aplenty. Watermen roaring up the docks in a sea of foam. Lazy sunsets enjoyed from the deck of your boat. Easy music to enjoy at one of the Eastern Shore’s premier venues. Old time hospitality at a 90-year-old bar. Cutting edge cuisine or laid down home cooking at one of the town’s more than a dozen eateries. 

Having survived storms, fishing regulations, and the shift from commercial to recreational fishing, Rock Hall residents have fought hard to retain the town’s traditional flavor.

A bit of history

A fishing settlement has existed near Rock Hall since the 1600s, and the town became a stopover for colonial travelers. George Washington passed through Rock Hall eight times, traveling there by boat from Annapolis and proceeding by horseback onto Philadelphia. Later, Rock Hall was a shipping center for agricultural products such as pears, peaches, and tomatoes.

Some say Rock Hall got its name from an unusually large “haul” of rockfish (striped bass). Indeed, as Kent County Commissioner and former commercial fisherman Ronnie Fithian says, “Without exaggeration, there was more tonnage of rockfish caught out of this little town than any one town on the entire East Coast of the United States.” Recreational fishermen, who began traveling to Rock Hall around the 1880s, also caught rockfish.

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Waterman’s Day celebrates the men and women of Rock Hall who make a living fishing local waters. Photo courtesy of the town of Rock Hall

The mid-1980s moratorium on commercial and recreational rockfish fishing affected many fishermen in Rock Hall. Some went into clamming, eeling, and crabbing; many others stopped fishing altogether. The commercial dock area of Rock Hall harbor called Hubbard’s Pier was sold, and the harbor was dredged to accommodate deep-draft recreational sailboats. The historic Rock Hall Mansion was torn down, and condominiums were built in its place. New, full-service marinas and businesses opened, and the town became a popular destination for recreational boaters.

Pirates, Fireworks, Music & More

During the Pirates and Wenches Festival, this year held August 9-11, there’s nonstop action as the town shows its wild side with bands of marauding pirates roaming the streets much to the delight of the more than 5000-plus visitors who crowd the town in search of grog and fun. A little sea chanty celebrating Rock Hall’s fictitious pirate history goes like this:

“Hail Rock Hall, Hail Rock Hall 
Long live Graybeard—Pirates are we all 
Pirates are we all—pirates are we all 
Long live Graybeard—Hail Rock Hall”

And one of the Eastern Shore’s most ambitious Fourth of July Weekends unfolds across the little hamlet with food, fireworks, and the not-to-be-missed Waterman’s Festival. (See sidebar for key events and dates.)

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Dinghies come ashore during the annual Pirates and Wenches weekend. Photo by Bernadette Van Pelt

But these two signature events are just part of the reasons boaters of all shapes and sizes traditionally give the little town of 1200 a “thumbs up” as a premier boating destination no matter the season.

“We do our best to put on a good show during our festivals,” says Mayor James Cook. “But a lot of visitors like our quiet weekends, too, where you can chill out by the water at one of our boater-friendly restaurants or bars or just sit back on your own boat and watch the sun meet the Bay in one of our spectacular sunsets.”

If music is your thing, be sure to check out the summer offerings at the venerable Mainstay. This funky music venue has something for every musical taste from rootsy rock to Appalachian folk… all served up in a 100-year-old storefront that has played host to jazz greats like guitarist Charlie Byrd in its storied history. The Mainstay is particularly renowned for its reputation for jazz excellence dating back to our earliest concerts and continuing to the present day with acclaimed jazz figures from all along the Eastern seaboard. Check out this summer’s guest artists at

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Get the Scoop ice cream. Photo courtesy of the town of Rock Hall

Many Rock Hall restaurants have musical performances over the summer weekends, including:

  • Harbor Shack 
  • Waterman’s Crab House  
  • Blue Heron Oyster House  
  • Maggie’s Coleman Tavern

One brand new fun music themed event is Porch Fest, May 26. Several notable properties around town host live music on porches, gazebos, and stages throughout the day. 


Wandering down Main Street with a dripping ice cream cone in your hand is one way to kick back and enjoy the small town feel of Rock Hall. Guests are encouraged to slow down, smell the roses, and partake of an ice cream cone or milkshake from one of Main Street’s two ice cream stores, the venerable Durdings and Get the Scoop. 

Rock Hall has been busy adding new establishments to its already array of dining destinations, including:

  • Blue Heron (great food with occasional “celebrity watermen” oyster shuckers who raise money for the Waterman’s Association; casual deck with games and music and more refined but still semi-casual indoor seating).
  • The Rock (local seafood in a casual atmosphere; great weekend brunch). 
  • The Rock City Café (great spot for breakfast, lunch, or dinner. Pizzas, too).
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The author samples oysters at Waterman’s Crab House.

Add these to the Harbor Shack and Waterman’s Crab House for a great taste of the Shore and you can see Rock Hall has something to suit every taste. Both venues offer a view, plus plenty of fresh Eastern Shore seafood. For a little more upscale dining, the Inn at Osprey Point offers white-tablecloth service featuring creamy lobster bisque and its signature crab cakes. Wednesdays are burger nights. And for the morning caffeine fix, get your cup of Joe at Java Rock on Sharp Street. 

No visit to Rock Hall would be complete without a stop at the nearly 100-year-old bar, Maggies. Maggie’s Tavern (established in 1932) is celebrating 92 years of continuous family ownership. It is the “local place that welcomes visitors with open arms. The ceilings are a little low… but the beer is cold, and the conversation is fresh.” Yelp calls it “The best dive bar in Rock Hall.” 

From the Water

Approaching Rock Hall Harbor from the water is pretty straightforward. The entrance channel leads north between converging breakwaters to two channels within the harbor. One channel leads to an anchorage basin at the west end of the harbor, then eastward paralleling the waterfront at Rock Hall to a basin at the east end of the harbor. There are a number of marinas in and around the Rock Hall area. They include:

  • Haven Harbour Marina
  • Lankford Bay Marina
  • North Point Marina
  • Osprey Point Marina 
  • Rock Hall Landing 
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Colleen Ligibel at the helm coming into Rock Hall. 

Marinas fill up during special events. Be sure to make plans ahead of time. Have a great time. And don’t mind the muck. It’s easy on boat bottoms, and the memory of one’s encounter with it are easily erased with a tot of rum. If you need to provision your galley, just head to Fresh Start, Bayside Market or the Deli at Rock Hall Liquor. And, if you like gas station food, check out Shore Stop.

Locals have plenty of “secret” spots to lay back and enjoy life. Here are a few of them: 

“Watching the sunset from our town beach… or from the deck of your own boat anchored in Swan Creek.”

“Grabbing some fresh crabs from Chester River Seafood.” 

“Just chillin’ in the Eastern Neck Wildlife Refuge.”

No matter your frame of mind, Rock Hall Mayor James Cook promises to roll out the red carpet for visiting boaters. “We are a boating community with a twist. We like to show people a good time… with great local festivals, fresh as-can-be seafood, and outstanding Eastern Shore hospitality. Come for one of our special events. Come back to kick back and enjoy life Rock Hall style.” 

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The author en route to Rock Hall.

Save the dates:

Annual Fourth of July celebration July 3-4

Traditional old fashioned Fourth of July celebration complete with marching bands, cold watermelon, dogs dressed up like Uncle Sam, and more red, white, and blue bunting than you can shake a stick at. Fireworks over the harbor July 3; Parade, games, Flat Race July 4.

Waterman’s Day activities, Rock Hall Bulkhead, July 7

Waterman’s Day celebrates the men and women of Rock Hall who make a living fishing local waters. The event showcases boat handling skills with such events as Most Patriotic Work Boat Contest, Anchor Toss Contest, and Work Boat Docking Contest. Be advised: spectators are cautioned to look lively for possible drenchings from boat captains “who come in a little hot” when attempting to dock their craft. Don’t forget fishing. Rock Hall boasts one of the most active charter fishing fleets on the Eastern Shore.

Pirates and Wenches Weekend, August 9-11

Now in its 17th year, the festival boasts a full measure of aarghing for mateys young and old (5000 of them last year). Highlights include a decorated dinghy contest, rum tasting, a Caribbean-style beach party, sea shanty sing-along, and enough Pirates and Wenches strolling around to make Captain Jack Sparrow proud.

For more information and a full calendar of events, visit

By Craig Ligibel