Weekends on the Water

Destination: Deale 

By Jody Argo Schroath 

This summer, we’re taking you on a short cruise around our local waterways, diving into some of the best waterfront destinations. Whether you come by boat or just want to feel like you did, get away for the weekend to these close-to-home locales.  

First up is South County’s own Deale. Let’s set our course for Herring Bay, a paradise for angling and relaxing, in the first of CBM Bay Weekly’s Weekends on the Water. 

Why You’ll Want to Go 

Herring Bay looks on the map like a giant thumbprint pressed into the western shore of the Bay between the West and Patuxent rivers. With its fertile land and easy access to rich fishing grounds, Herring Bay has been attractive from the earliest colonial days. You won’t find many traces of those days left. But once there was a town of Herrington, and during the War of 1812, there was a fortification on Town Point at the mouth of Rockhold Creek on the north end of Herring Bay. Here, a determined American lieutenant fired a lone cannon at a large party of British marines heading for shore. The cannon fire did no harm, but it did annoy the soldiers, who immediately swarmed ashore. The desperate lieutenant lit off another round, but the cannon slid off its mount and onto his foot. As his four fellow soldiers fled the scene, the unfortunate lieutenant hobbled painfully along behind them. The British set fire to a tobacco barn and left. The lieutenant was fine. And that is the story of Herring Bay’s part in the War of 1812.  

That section of Rockhold Creek is now home to Herrington Harbour North, one-half of one of the largest and most luxurious marinas on the Bay and home to the Bay’s largest collection of skilled marine contractors. Herrington North even has its own West Marine. The other half of Herrington Harbour, by the way, is located at the bottom end of Herring Bay. 

Today, Rockhold Creek is lined with marinas, large and small, fancy and downhome, along with a couple of very popular dock bars and a large fleet of charter fishing boats, many of which cleverly make their home at those very popular dock bars. 

So why are we sure you’ll want to spend time in Deale? Because you can fish some of the Bay’s best waters, either on your own boat or with one of the charters. You can spend the weekend relaxing on a staycation at one of Herring Bay’s marinas, The Inn at Herrington Harbour (South) or Hidden Harbour’s Anchored Inn, and sampling seafood. Or as Shipwright Harbor’s Jed Dickman modestly puts it, “It’s a wonderful, ideally located spot, where you can find everything you could possibly want.” 

Starting smack in the middle of the Bay means easy jaunts by boat to Eastern Bay and St. Michaels as well as the Choptank River and Oxford or Cambridge. And of course, all those lovely fishing grounds are right here. With Annapolis about 15 miles north and Solomons about 30 miles south, Herring Bay is a convenient destination as well as a central starting point. 

What to Expect 

Now, let’s get the lay of the land. We’ll start at the south end of Herring Bay, which is occupied by Herrington Harbour South, tucked neatly within its own basin. If Herrington North is all about mixing work and play, then Herrington South is all about play. It has its own special restaurant (more about this later), its own hotel, swimming pool, and beach. And of course, its own marina and fuel dock. It’s a whole resort in one neat package. This is the kind of place where people come to get married. 

On the north end of Herring Bay—about two and a half miles away—the action centers on Rockhold Creek. Here, as we mentioned earlier, lies Herrington Harbour North (logically), as well as a fistful of other marinas, like Shipwright, Paradise, Rockhold Creek and others that we’ll get to as we go along. Here, too, are those popular dock bars and, beyond the first bridge, a couple more marinas for smaller boats and the town of Deale. During the boating season, a water taxi neatly connects the two ends. 

If you are coming by boat 

Once you get to Herring Bay, the most important thing to know if you have a draft more than three or four feet is that there is a long finger of shoal water that extends from the north end of the bay nearly two miles south or within a half-mile of the south end. Yes, there are ways to cross it, but if you don’t know the waters, you are better off playing it safe by following the markers. If you are heading to Herrington South, it doesn’t matter, of course. Nor is it an inconvenience if you are coming up from the south. If you are coming from the north and are aiming for one of the north-end marinas, come down to the red “2” and then follow the markers north in deep water. 

The channel entrance into Herrington South’s basin is straightforward and deep, but on the other end, the short section of channel from the Rockhold Creek breakwater to markers “8” and “9” is narrow and can be crowded on weekends and shallow in spots to about five or six feet at dead low tide. At markers “12” and “13”, the channel for Herrington North splits to port while the main channel continues north then northeast to reach all the other marinas and the dock bars. 

Coming up Rockhold Creek channel, Skipper’s Pier Restaurant and Dock Bar is the first thing you’ll find to starboard. This is quickly followed by Paradise Marina, also to starboard, and then Shipwright Harbor Marina’s extensive docks to port. Family-owned Hansel’s Marina and Nugent Marina follow to starboard and then Happy Harbor Restaurant to port. Happy Harbor is the dock bar we mentioned with all those conveniently-located charter boats. Under the Deale Road bridge, which has a vertical clearance of 14 feet, lie Harbour Cove Marina, a popular location for smaller boats with shallower drafts, and finally Hidden Harbour, which is home to the Anchored Inn

If you are bringing your boat (or not) 

We’ll let you Google Map your way off the main highways into Deale. When you get ready to splash your boat, you’ll find the sole area boat ramp at Harbour Cove Marina on Rockhold Creek. The Anchored Inn is conveniently nearby. The trip out of the creek and onto the Bay is quick and easy. 

If you are bringing a canoe or kayak, you’ll find a number of places to launch, including the beach at Herrington South and other soft-launch locations at most of the marinas on Rockhold Creek. From there, you can explore Herring Bay and Rockhold Creek, which meanders peacefully above the Deale Road Bridge for about two miles. You can also explore adjacent Tracy’s Creek above the S.R. 256 Bridge north of Herrington Harbour North for about a mile. 

Where to Stay 


If you are looking for an all-inclusive family get-away-from-it-all weekend, you may want to head directly for Herrington Harbour South. Here, you’ll have easy access to the Bay from the comfort of its entirely protected boat basin. There is an excellent restaurant and your own sandy beach and swimming pool a few steps away. You may even decide to get off the boat and stay in the inn. For lighter meals, as well as beer and wine, simply walk across the street to Chesapeake Market & Deli. 

On the other hand, if you go to Herrington North, you can have dockage, a pool and fitness center, get some boat work done, and sample a couple of classic local hangouts in nearby Deale. 

Then again, if you bear right coming up Rockhold Creek and take a slip at Shipwright Harbor Marina, you can find plenty to make you happy, including dinghy or water-taxi access to the local favorites Skippers Pier and Happy Harbor, a saltwater pool, bikes, and kayaks. 

Above the Deale Road Bridge, you’ll find two more good options, especially if you are trailering your boat in. Harbour Cove Marina has wet and dry slips, a pool, a clubhouse and it’s within walking distance to restaurants and a hardware store. Just beyond, Hidden Harbour Marina offers slips, a playground for kids, the Boathouse Bar for adults, and the popular Anchored Inn for those who prefer to stay ashore. Globally famous Weaver Boats, which builds exquisite, big-game sportfishing yachts, is located just next door. 


If you want to stay ashore and still take advantage of all Herring Bay has to offer, you have two good choices, both of which we’ve mentioned earlier. The first is The Inn at Herrington Harbour South and the second is the Anchored Inn at Hidden Harbour Marina.  

Things to Do 

Do you want to relax and get away from it all? Then Herring Bay is a terrific choice. Do you want to get out on the water, either in your own boat or as part of a fishing charter? You could hardly make a better choice. Fishing, sailing, and exploring the backwaters by paddlecraft: it’s all here. If you don’t have a paddlecraft, you can rent one from Chesapeake Paddle Sports next to Paradise Marina. If you just want a tour of the local creeks, call Twin Creeks Taxi and Capt. Z will appear in his pontoon boat, Solo Cup, to make it happen. Shoot, there may even be a trivia game involved. 

It doesn’t matter whether you choose the north or south end of the bay, because you won’t be separated from the other end. Simply call or hop aboard Capt. Z’s water “Tax-Z” (443-995-9957), which generally runs Friday and Saturday during the boating season.  

Take a shopping trip to the many antique and consignment stores in Deale to hunt for treasure of a different sort. Cap it off with lunch, which brings us to… 

Where to Eat 

Let’s start with the first of Deale’s iconic Chesapeake dock bars, Skipper’s Pier Restaurant & Dock Bar. Just inside Rockhold Creek, owners Dave and Jessica Rosage have combined their training in business management and culinary arts to set Skipper’s apart from your average dock-and-dine facility. You can get here on your own boat, on your dinghy, paddlecraft, or by water taxi. Oh, yes, and by car. 

Deale’s second of four dock bars is the famous Happy Harbor waterfront restaurant, which has been serving local watermen, residents and visitors since 1933. Wow! You can get everything to eat here from fried pickles and steamed clams to a cheeseburger and catfish dinner. All the while, you can enjoy the congenial company and watch the charter boats come and go. The third and fourth? Dockside Restaurant and Bar at Herrington North and the Boathouse at Hidden Harbour. 

And there’s more! Whether you stay at Herrington Harbour South or not, you’ll want to go for dinner at Ketch 22 restaurant. Here owners Bobby and Julie Jones oversee an inspired menu of regional food. Bobby is also co-owner of the wildly successful The Point Crab House and Grill on Mill Creek in Arnold. The menu at Ketch 22 includes crab gazpacho, braised pork and cabbage, and ricotta pie and berries.  

When you’ve had enough water views and go wandering the shops in town, South County Café is a perfect lunch stop. 

While the names and places here may not be new to you, we can all use some inspiration to answer the age-old question: What should we do this weekend? So cast off the lines (or buckle your seatbelt) and spend a weekend on the water in Deale.  

Editor’s note: Chesapeake Bay Magazine cruising editor Jody Argo Schroath knows all the best spots from Havre de Grace to Cape Charles, and she’s hard at work putting together even more tempting Bay destinations. Look for CBM’s special edition Weekends on the Water, covering the whole Chesapeake, out in early August. And keep reading Bay Weekly for adventures in our neck of the Bay all summer long. 

Destination: Deale Details 


Hidden Harbor Marina: Home of Weaver Boatworks, 90 wet slips, in-and-out service, and full mechanic shop. 600 Cabana Blvd., Deale, MD, 20751, 410-867-9666, 

Herrington Harbor North: 389 Deale Rd., Tracy’s Landing, MD, 20779, 

Herrington Harbor South: 7149 Lake Shore Dr., North Beach, MD, 20714,  

Shipwright Harbor Marina: 6047 Herring Bay Rd., Deale, MD, 20751, 

Tri-State Marine:  5861 Deale Churchton Rd., Deale, MD, 20751, 410-867-1447,

Paradise Marina: 6136 Drum Point Rd., Deale, MD, 20751, 301-832-6578 

Hansel’s Marina: 6062 Drum Point Rd., Deale, MD, 20751, 301-854-9449 or 301-855-4632 

Nugent Marina: 601 Deale Rd., Deale, MD, 20751, 410-867-0354 or 301-261-9685,

Harbour Cove Marina: 5910 Vacation Lane, Deale, MD, 20751, 301-261-9500, 

Rockhold Creek Marina: 453 Deale Rd., Deale, MD, 20751, 833-425-2423,  

Town Point Marina: 6100 Leitch Ln, Tracys Landing, MD, 20779, 410-257-7074


Anchored Inn: Anchored Inn Hotel is the only hotel in Deale. This boutique hotel with boat access and balconies sits on the waterfront and is the home of the Boathouse Bar. 604 Cabana Blvd, Deale, MD, 20751410-867-9668[email protected] 

The Inn at Herrington Harbour (South): 7161 Lake Shore Dr., North Beach, MD, 20714, 


Boathouse Bar & Galley Food Truck: The Boathouse has live music every Saturday and Sunday and classic car shows every other Wednesday. Winner of CBM Bay Weekly’s Best of the Bay for Best Bar, Best Happy Hour, Best Live Music and Best Crushes, this is not your typical watering hole—the bartenders serve guests from inside a boat that has been constructed into a bar and serve drinks around the “house” of the boat. 604 Cabana Blvd, Deale, MD, 20751, 410-867-9668, 

Happy Harbor: Dine on the pet-friendly dock, enjoy breakfast seven days a week and live music on the weekends (F 5-9pm, Sa 4-8pm & Su 3-7pm) till the end of September. Open 8am to midnight. 533 Deale Rd, Deale, MD, 20751, 410-867-0949, 

South County Café: South County Cafe serves fresh local seafood and is known for its world-famous homemade pies. Keep a look out for the 27th annual pie run this November. Follow the Facebook page for daily specials. 5960 Deale Churchton Rd., Deale, MD, 20758, 410-867-6459; 

Skipper’s Pier Restaurant & Dock Bar: 6158 Drum Point Rd., Deale, MD, 410-867-7110, 

Dockside Restaurant & Bar: 421 Deale Rd, Tracy’s Landing, MD, 410-867-1138 

Ketch 22: 7153 Lake Shore Dr., North Beach, MD, 20714, 443-646-5205 

Chesapeake Market & Deli: 7150 Lake Shore Dr., North Beach, MD, 20714, 410-257-7757, 


A Vintage Deale: Garden accents have arrived. Stop by for one-of-a-kind home finds. 655 Deale Rd., Deale, MD, 20751, 443-203-6157, 

Second Wind Consignments: This shop is celebrating 12 years in Deale this July and has not “skipped a beat because of Covid” when it comes to accepting consignments or maintaining inventory levels. Open Wednesday through Saturday EVERY week and consignments by appointment. 661 Deale Rd., Deale, MD, 20751, 410-867-0480, 

Blue Heron Boutique: 645 Deale Rd., Deale, MD, 20751, 410-980-4722, 

Vintage by the Bay: 645 Deale Rd., Deale, MD, 20751, 443-875-8039, 

My Fancy Finds: Stop by this home-grown and family-owned mobile & online women’s boutique. Shop on board the MFF bus named Birdie or download the free app ( & save $10 on your first purchase (Code: BAY104U — expires 6/30/21). 5950 Deale Churchton Rd. Suite B, Deale, MD, 20751,