Deale – What’s There and How to See It

Deale, Maryland, is a modern fishing village on the Chesapeake Bay’s Western Shore. It’s not a quaint, picturesque village. Deale is a modern fishing community forested with sailboat masts clanking like chimes all along the large protective creeks that empty into the Bay.

One of the several marinas in Deale

Deale is where you go for a fishing charter or to sit at a waterfront restaurant with a great view facing west across the Chesapeake Bay.

There is no city center or downtown. Stores and offices are scattered along Route 256. That’s where you’ll also find a few antique stores and consignment shops.

Shopping in Deale, MD

Deale is all about life around the water.

Charter Fishing & Boating

You can arrange fishing charters in nearly every Chesapeake Bay town listed on ChesapeakeLiving, but other historic towns have something else going on.

In Deale, it’s fishing and places to hang out after a day of fishing.

Nearly 70 Charter Fishing boats are docked in the Deale area. That’s the most of any Maryland town on the Chesapeake Bay.

Charters next to Happy Harbor are just some that are available

The charters can go north for fresh water fish or south for salt water fish.

As for boating, marinas around Deale are huge, like boat cities with sailboat neighborhoods or power-boat districts. Some of the marinas have inns with pools.

Rockhold Creek channel to the Chesapeake Bay

Until you go under a bridge that’s too low for a sailboat, then its power-boat marinas.

Boat owners from Washington, DC and Baltimore who want a quick entrance to the Bay keep their boats around Deale.

You’ll find fishing charters near all of the big bars as well as other marinas. It’s best to call ahead to arrange a trip, but you might be able to show up on the day of and find a captain hanging out and willing to take you on the water.

Deale Restaurants & Bars

Deale faces across Drum Point and into the Chesapeake Bay. Because of that, Deale restaurants are popular and they have lively boater bars, often with live music on the weekends.

Facing west means no sunset right? Actually, the sun often reflects off the clouds across the Chesapeake Bay and turns them into glowing pink or orange cotton-candy floating above the water.

Happy Harbor

One of the best-know hangouts, and certainly the oldest, is Happy Harbor (533 Deale Road, Deale, MD). You can catch a charter boat there or a deep-fried rockfish basket lunch.

From the road, it looks like a shack and is easy to drive right by. So keep an eye out.

It’s a popular dive bar where watermen and charter captains go for a burger and beer after work.

Happy Harbor outdoor seating & tiki bar

Fishing reels are mounted on the low ceiling. The bathroom sign says, “Used Beer Dept.” And, behind the bar, old red and green channel marker lights hang on the right (red) and left (green).

Happy Harbor’s specialty is a large selection of “crushes.” You can’t get a frozen daiquiri there.

Boat House at Anchored Inn

Boat House bar & grill in Deale, MD

The Boat House at Anchored Inn (600 Cabana Blvd, Deale, MD) really is a boat house. Inside, is the Southern Belle, a former waterman’s boat that’s been sunk into the cement floor and is now a bar.

Boat House bar is a former oyster/crabbing boat

Boat motors and fishing equipment hang from the ceiling. The bar stools are made from boat stands (the scaffolding that prop up a boat when it’s on land).

It’s a bar and grill next to the Anchor Inn located on the edge of Rockhold Creek on its way to Herring Bay.

The grill is a food truck that pulls up neatly to a opening in the boat house wall.

The Boat House is in Hidden Harbor Marina and you might have to share the parking lot with boats on-the-hard (being repaired).

During the summer, you’re greeted by a small bar stocked with canned beer and homemade crushes in quart glass-jars.

They have live music on the weekends during boating season.

Skipper’s Pier Restaurant & Dock Bar

Skipper’s Pier Dock Bar in Deale

Skipper’s Pier Restaurant and Dock Bar (6158 Drum Point Rd., Deale, MD) is at the end of Drum Point Road, on the Drum Point peninsula. (Drum are a type of Chesapeake Bay fish.)

Drum Point is also the entryway for boats to get to a number of marinas in the various creeks. Skipper’s has a sizable dock to encourage captains to swing by.

Skipper’s gets busy late afternoon and they don’t take reservations. A two-level outdoor bar is perched on the dock to make the wait easier.

Captains who stop there are known by the name of their boats. Conversations start easily, over how someone did in the previous Wednesday night sailboat race or weather conditions during the last powerboat cruise.

Dockside Restaurant & Sports Bar

Dockside Restaurant & Sports Bar in Deale, MD

Dockside Restaurant & Sports Bar (350 E Bay Front Rd, Deale, MD) offers picturesque views of the marina, casual dining, and a relaxing Maryland, South County experience.  

They also have live music on the weekends and lovely outdoor seating on their lawn facing the docked boats.

Deale Water Taxi

Deale’s Tax-Z, a shuttle among marinas & restaurants

Several Chesapeake Bay towns have water taxi’s, but Deale has the Twin Creeks Tax-Z to take you from bar to restaurant along the Deale waterways.

Tax-Z Captain Dennis Zimmerman, dings a bell as he goes by the bars. But the boat doesn’t stop unless you call. You can rent it for a private charter, or use it as easy transportation to the next place.

You can also use it for a fun boat ride around the Deale marinas.

The boat is out of Shipwright Harbor Marina and accepts donations for the captain. There’s no charge for the ride.

It runs on Saturdays, 3pm-7pm unless you call and make other arrangements. It won’t run in foul weather.

Herrington Harbor Historic Museum

Just past the Deale Road restaurants is an Historic Village and Deale Area Museum at the entrance of Herrington Harbour North Marina (389 Deale Rd., Tracey’s Landing, MD). 

Historic village just outside Deale

The marina owners, Steuart (father) and Hamilton (son) Chaney, collect local 19th century buildings.

It started in the late 1980s when Steuart bought the one-room schoolhouse where his great-aunt taught and moved it to Tracey’s Landing, just outside Deale. 

Since then, the Chaneys have added a log smokehouse, an African-American meeting house, along with an outhouse — for show only .

The meeting house was actually an African-American beneficial society building. Before insurance, people paid into beneficial societies for sickness- and burial-benefits. This society lasted until 1983.

The building collection has been there since the 1980s. But it wasn’t until the Deale Historical Society was formed in 2005 that the museum came together.

“(Steuart) had the museum, but nobody to show it,” says Ruth Hazen, Deale Area Historical Society Collections Manager. “We had the time, the docents and the artifacts, and so it makes a good marriage.”

Awaiting renovation across the road is a slave cabin and tobacco barn.

Renovation of a Greek Orthodox chapel is underway, but it’s still in the fixer-upper area across the road from the museum.

Greek Orthodox chapel being restored at Harrington Harbor near Deale, MD

The Historic Village Museum is open to visitors on Sunday afternoons May through October, 1pm-4pm. The museum charges no fees and a visit is free.

The buildings are open only when a volunteer docent is available.

“It’s not very pleasant here in the winter,” says Ruth.

None of the buildings have heat for the retirees who serve as docents.

Next to the village is St. Mark’s Chapel, part of St. James’ (Episcopal) Parish. The chapel is not part of the museum.

St. Mark’s chapel

In 1876, the Weems family deeded one acre of land because a son died at seas and needed a burial spot.

This isn’t the original chapel. That one burned in 1960s and was rebuilt.

Members of the Weems family are buried in the nearby family plot.

Weems family cemetery behind St. Marks. The water & marina are in the background.

“George Weems, he’s the one who started the steamboat company in the 1902s, the Weems Line,” Ruth points out. The line traded along the Bay and shipped to Baltimore.

A town in Virginia is named for the Weems family on the Rappahannock River near where it enters the southern end of the Bay.

“The buildings are interesting if you know the history,” says Ruth. “Otherwise you’re just looking at old buildings, some of them falling apart.”

Cycling Around Deale

The Deale area is popular among cyclists.

Route 2 (Solomons Island Road) has wide shoulders and rolling hills. Great for a long ride.

For a scenic ride, turn onto one of the many country roads that loop toward the water. The side roads, including the roads going into Deale, don’t have shoulders, but usually don’t have a lot of car traffic.

Expect some steep hills as those side roads take you from the top of the Route 2 ridge down toward the water and back up.


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