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My book Shore Fun: The Delmarva Wanderer’s Guide features snapshot descriptions of more than 125 destinations on the Delmarva Peninsula. Plus, more than 150 annual events, broken out conveniently by season of the year. Below is one sample destination, a history-laden and scenery-filled adventure along backroads on the lower Eastern Shore of Maryland. Info on the book here.

On the road to Deal Island (Route 363), you will pass through Dames Quarter—that’s a gussied-up version of “Damned Quarter,” its original name in rougher and tumbler times gone by. Find your way there along narrow Riley Roberts Road into the Deal Island Wildlife Management Area, a 13,000-acre hiking, paddling, fishing, and hunting gem.

Deal Island, too, has a gussied-up name—it was “Devil’s Island” in those rougher days. Today, it’s an old-school watermen’s community, with most houses lined up along a thin backbone of high ground that ranks as “high” only in comparison with all the other land here. Stop at the Skipjack Heritage Museum to learn more about those watermen, their families, and their ways.

Stroll the grounds at St. John’s Methodist Church and visit its little Joshua Thomas Chapel. That chapel honors a fascinating 19th century preacher known as the “Parson of the Islands.”
Otherwise, just stroll docks full of workboats, watch the locals unload the day’s catch, grab a sandwich at the old-time country store near the harbor, and think about the fact that the scenes and rituals of everyday island life that unfold in front of you here are ones that really haven’t changed very much for centuries now.

If you want to visit an even more remote watermen’s community, find the route through Fairmount (where you can wander the grounds of the old Fairmount Academy) and out to the town of Rumbley. As of this writing, there was a tiki bar waiting at the end of that backroads adventure.

• Tourism info: Somerset County (Md.) Tourism

Info on this and all my other books is here.

–posted by Jim Duffy for Whimbrel Creations LLC/Secrets of the Eastern Shore in May 2024. All rights reserved. Thank you for spending time with this piece and on this site.

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