On their two-year quest to visit and explore all of Maryland’s counties, Diane and Jeff Caslow, set their sites on Maryland’s southern most county of Somerset for a summer road trip.

From the Caslow Travelogue

We took off on a hot summer day to explore a bit of history, preservation and the ultimate sugar buzz from Maryland’s official state desssert of Smith Island Cake. Our guidebook for the road trip was a copy of “Somerset 350 – Where History Lives 1666-2016,” a publication produced for the 350th Anniversary of Somerset County and available as a PDF online.

Deal Island

Typical for our trips, we like to go off beaten path to begin our exploration.

Deal Island has a small historic district, and the most exciting part is the discovery of working skipjacks, and ones being lovingly repaired.  We saw a sign for Skipjack Heritage, Inc. an organization that promotes appreciation for the Skipjacks, their owners, captains, crews and families, as well as the seafood industry and the watermen’s way of life in general, in order to preserve the social and cultural heritage for current and future generations.

Skipjack Nathan of Dorchester. Photo from Last Skipjacks Project.

Skipjack Nathan of Dorchester. Photo from Last Skipjacks Project.

Before skipjacks, canoes were some of the earliest vessels used to travel between the islands on the lower shore. There is a historic marker, easily missed, noting Reverend Joshua Thomas who served congregations, reaching them by sailing in his log canoe in the early 1800s.

Photo from WAMU.

Photo from WAMU.

Stopping in at Lucky’s Last Chance General Store for coffee and homemade cake also allowed us to admire a mosaic in tribute to life on the water.

Princess Anne

Princess Anne is the county seat established in 1733 and gained importance as a market center because of the river trade. Much of the town’s architectural heritage has been preserved and is on the National Register of Historic Places as the Princess Anne Historic District. There is a self-guided walking tour with a downloadable app. It gives more detail on each of the sites in the town that was fun to use.

There are buildings preserved to be admired, those in continual use in some form and those adapted for a new purpose. There are beautiful examples of early churches, including Manokin Presbyterian Church,  the Teackle Mansion, built in the early 1800s and the Washington Inn and Tavern, in operation in some form since the late 1700s.

We were able to check out as many of the sites as we could, as we had to get to Crisfield to catch the Smith Island afternoon ferry. We could not linger long, so we plan on coming back…



We did a short walk around Crisfield while we waited for the Smith Island ferry. We could have done more, but we spent most of our time in the Crisfield Visitor Center, staffed by none other than the recently former Mayor of Crisfield, Kim Lawson. We were in luck as he told us about the history, way of life, preservation going on in the area and his deep and passionate knowledge of Crisfield. In the late 1800s  John Crisfield, a Princess Anne attorney, was instrumental in bringing the Eastern Shore Railroad, a branch of the Pennsylvania Railroad system, to Crisfield, which provided an opportunity for seafood, especially crabs, to be shipped all over the United States. Crisfield became known as the Seafood Capital of the World, a nickname still carried by the city. In the early 1900s, the oyster harvest was surpassed by the crab industry. In 1910, 120 million soft crabs, 25 million hard crabs and 700,000 gallons of crabmeat were shipped. We checked out some of the shops and the exhibits at the Governor J. Millard Tawes Musuem before heading to the city dock.

Smith Island

Half of the fun is getting there and you can choose the narrated sight-seeing version or the regular delivery boat. We chose the latter, on the Captain Jason II. We shared the forty-five minute ride to Ewell with an assortment of people and struck up conversations along the way.

Image of homemade Smith Island Cake

Once we docked at Ewell, we followed  the road to the Bayside Inn for crab cakes and, yup, homemade Smith Island Cake, the state cake of Maryland. Beginning in the 1800s, Smith Islanders would send these cakes with the watermen on the autumn oyster harvest. The bakers began using fudge instead of butter cream frostings, as cakes frosted with fudge lasted much longer.

We rented bikes for our own tour around the island, checking out the beauty of island and a way of life preserved. We explored the exhibits in the Smith Island Cultural Center.  And just like that, it was time to catch the ferry back, and swap stories of our afternoon adventures.

Ward Brothers Workshop

Our final stop as we headed  out of Crisfield, was the Ward Brothers Workshop, where Lem and Steve Ward  perfected decoy carving and are considered  the icons of the wildfowl carving community. The workshop was not open, but peering inside we saw that it looks the way it did when Lem and Steve were there. A nice way to end our day!