Deale is a fishing village on the Chesapeake Bay’s Western Shore. Not a quaint, historic village; a modern fishing community forested with sailboat masts clanking like chimes all along the large protective creeks that empty into the Bay. Charter fishing is a main industry there.

One of the several marinas in Deale
One of the several marinas in Deale

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. Deale is all about life around the water.

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

Here’s the thing about Deale, it faces west across the Bay. It’s the place to be for sunsets. And because of that, it’s popular for the restaurants and lively outdoor bars.


Skipper’s Pier Dock Bar in Deale, normally surrounded by boats during season

Skipper’s Pier Restaurant and Dock Bar (6158 Drum Point Rd) is  one of the main restaurants that locals mention. It’s at the end of Drum Point Road and on a peninsula facing the sunset. It’s also the entryway to a large number of marinas in the various creeks, with 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.

Happy Harbor from the road. It's easy to miss.
Happy Harbor from the road. It’s easy to miss.

Captains who stop there are known by the name of their boats, and conversations at Skippers easily start over how someone did in the last Wednesday night sailboat races or weather conditions during the last powerboat cruise.

One of the best-known hangouts, and certainly the oldest, is Happy Harbor (533 Deale Rd). 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.

Charter boat captain cleans the day’s catch on the dock next to Happy Harbor

It’s a popular dive bar where watermen and charter captains go for a burger and beer after work. Fishing reels are mounted on the low ceiling. The bathroom sign says, “Used Beer Dept.” Behind the bar, old red and green channel marker lights hang next to large flat screen TVs showing sports. You can’t get frozen daiquiri there; Happy Harbor’s specialty is a large selection of “crushes” — on the rocks.

You’ll find fishing charters behind and to the side of Happy Harbor. 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.

Calypso Bay tiki bar in Deale

The crushed-ice, fruity, rum-drink kind-of-place is a little farther down Deale Road, called Calypso Bay (421 Deale Rd). It’s more upscale yet still casual (think of going from working boat territory to land of cruising boats). Calypso features a covered tiki-bar, and tables are set up on a sandy beach overlooking the boats.

Historic Museum

Historic village just outside Deale
Historic village just outside Deale

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). 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. 

Deale Historic Village - African American meeting house
African-American beneficial society building, also used as a meeting house. Before insurance, people paid into beneficial societies for sick and burial benefits. This society lasted until 1983.

Since then, the Chaneys have added a log smokehouse, a dairy building, an African-American meeting house, a corn house (which Steuart came across just as a bull-dozer was approaching to tear it down off Route 2), and a couple outhouses — for show only.

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.”

Deale Historic Village
Former slave cabin awaiting renovation

The Society oversaw the renovations of the buildings currently open to the public. Awaiting renovation across the highway is a Greek Orthodox chapel, a tobacco barn, and a slave cabin.

“It’s all private money, so you can’t push too hard,” says Ruth. It’s difficult to get grants because the buildings are owned by a private business. The museum charges no fees and a visit is free.

Local volunteers, called docents, stand by to answer questions. The Historic Village can be seen Sunday afternoons, summers only (May-October, 1pm–4pm). “It’s not very pleasant here in the winter,” says Ruth. None of the buildings have heat for the retirees who serve as docents.

St. Mark’s chapel

Next to the village is St. Mark’s Chapel, part of St. James’ (Episcopal) Parish. The chapel is not part of the museum. In 1876, the Weems family deeded one acre of land because a son died at seas and needed a burial spot. The chapel 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.
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.”


Deale Road is popular among cyclists. The road has no shoulders, but is a scenic country ride and connects to Route 2 (Solomon’s Island Road) which does have wide shoulders that are perfect for cycling.


Digiprove sealCopyright secured by Digiprove © 2018