Deale & Herring Bay

Can you say “great boating” and “excellent fishing”?
Then you can say “Herring Bay” and “Deale”!

Herring Bay looks on the map like a giant thumbprint pressed into the Western Shore of the Bay along the otherwise long and featureless stretch between the West and the Patuxent rivers. This welcoming indentation, with its fertile land and easy access to the rich fishing grounds of the Bay, have made it 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. 

Okay, that was a little off the point, but we like the story, especially since that section of Rockhold Creek is now home to Herrington Harbor 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 Harbor, 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 one of those very popular dock bars.

So why are we sure you’ll want to visit Herring Bay and the little town of 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 at one of Herring Bay’s marinas, The Inn at Herrington Harbour (South) or Hidden Harbor’s Anchored Inn, and sampling seafood and meeting a whole new set of soon-to-be friends. 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.”

Now, let’s get the lay of the land. We’ll start at the south end of Herring Bay, which is occupied by Herrington Harbor South, tucked neatly within its own basin. If Herrington North (the one we mentioned that lies near the old Town Point) is all about mixing work and play, then Herrington South is all about play. It has its own very 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 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 Harbor 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.

Herring Bay is the location of choice for boaters who live in the Washington D.C. area. For them, this is often the most convenient spot, about an hour, on a good day, from downtown. It takes about the same amount of time driving down from Baltimore and about two hours if you’re driving up from Richmond. Once you get there, you are smack in the middle of the Bay, which means easy trips to Eastern Bay and St. Michaels as well as the Choptank River and Oxford or Cambridge. And of course, all those lovely fishing grounds will be right there. Annapolis is about 15 miles north and Solomons about 30 miles south. All of which makes Herring Bay a convenient destination as well as a central starting point.

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 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 Sherman’s 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. As we mentioned it’s a pretty easy drive from Baltimore, Annapolis, and Washington. 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.


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, work-out room, have 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 dingy or water-taxi access to the local-favorites Skippers Pier and Happy Harbor, a saltwater pool, bikes, and kayaks.

Above the Deale Road Bridge, which has a vertical clearance of 14 feet, 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, and 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. 

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 paddle craft: It’s all here. If you don’t have a paddle craft, 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. In Deale itself, you’ll find the Deale Hardware & Home Center, South County Café, and Deale Umai Sushi House. 

This is always our favorite part, and here on Herring Bay, we’re particularly enthusiastic about the subject. 

Let’s start with two of the Chesapeake’s iconic dock bars, Skipper’s Pier Restaurant & Dock Bar, which, as we mentioned, is the first thing you’ll find on entering Rockhold Creek on the north end of the bay. 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, paddle craft, 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 make the trip there just to have 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 MD. The menu at Ketch 22 includes crab gazpacho, braised pork and cabbage, and ricotta pie and berries. ⚓︎