Now Reading
Experience Eastern Shore Vibes in South County

Experience Eastern Shore Vibes in South County

Every corner of Maryland is a gift to road trippers, and a visit to Southern Anne Arundel County (labeled South County by locals) is among the state’s many prizes worth seeking. My family, friends, and I enjoy this quiet niche of the Chesapeake Bay’s Western Shore because it feels like the Eastern Shore in miniature. All the bygone charm, leafy country roads, and dock bars with fine views that understandably pull people to the east can be found in the west.

Photo Credit: Chelsea McCallister

And being just a short drive from the Baltimore-Washington, D.C. metropolis, a South County road trip doesn’t require a Bay Bridge crossing and a tango with beach traffic! These are my favorite shore towns that represent picturesque South County:


Built around four separate creeks, Deale is home to the largest amount of deep-water protected boat slips on the Bay. It’s no surprise that its harbor is busy with working and leisure vessels alike. Deale is a great place to rent a charter boat and try your hand at sport fishing!

In addition to watercraft, Deale anchors attractive dining spots and antique shops. 

Photo Credit: Skippers Pier

My family loves the classic marina views and fresh catch menu at Skipper’s Pier Restaurant & Dock Bar. Their crab dip is chart-topping! Happy Harbor is another beloved dock bar where you can feast on fish or rent a charter boat to catch it yourself. 

Antique enthusiasts like my husband and I will love perusing mid-century collectibles at Somewhere in Time and elegant country treasures at A Vintage Deale

Photo Credit: Chelsea McCallister

If you’re looking to overnight in Deale, I recommend Anchored Inn at Hidden Harbor for nautically-inspired lodging hunkered right on Rockhold Creek. At The Boathouse Bar, order an Orange Crush from the bar that is literally a retired Chesapeake workboat.

Shady Side

In the 19th century, passenger steamers brought daytrippers from Baltimore to Shady Side. While the peninsula town is still very much accessible by boat, it’s also scenic road trip material.

If you find yourself in Shady Side on a Sunday between Memorial Day and Labor Day, do not skip the Captain Avery Museum. The historic home was built by an oysterman and boat captain in 1859; local volunteers now manage the waterside property and lush grounds. On a recent visit with friends, I was fascinated by the museum’s collection of shore life artifacts and stories about the people who farmed, fished, and fêted in South County.

Photo Credit: Chelsea McCallister

Another requisite Shady Side stop is a no-frills Shady Side Soft Serve. At first, you might question how quality sweet treats can be found in a nondescript commercial building next to a laundromat and car wash. But give it a chance! The reasonable prices and generous portions are so worth it.

The next time I return to Shady Side, I plan to walk the rustic trails at one of Maryland’s newest state parks—Franklin Point State Park. The 477-acre peninsula’s undeveloped marshland, wooded forest, and living shoreline are calling my name!


Established by Quakers in the mid-17th century, this secluded waterfront community has never exceeded a population of 500 residents. Recreational sailing and sport fishing help keep the peaceful vibes going well into this century.

This micro town can be easily explored in an afternoon. Here’s a suggested itinerary: Step into the past at the Galesville Heritage House (open only on Sundays from 1–4 pm or by appointment), nab yourself a crab melt at the nautically adorned Pirate’s Cove Restaurant and Dock Bar, and seek treasure at Capt’ Harvey’s Antiques & Collectibles or Re-Find vintage.

As you can see, Anne Arundel South County life is vibrant on water and land. I hope you can add these 5-out-5-star western Chesapeake shore towns to your next road trip itinerary!


Feature Photo Credit: The Boathouse Bar

About the Author

A native of Las Vegas, NV, Chelsea Milko McAllister resides in the historic Baltimore neighborhood of Charles Village with her new husband and stepson. Her foreign policy career and travel obsession have taken her to over 50 countries, including Uganda, where she served as a U.S. Peace Corps Volunteer. Chelsea loves documenting her Maryland adventures through writing and photography. Follow her on Instagram @themilkoway.

Maryland Road Trips is a part of Postern Publishing.
© Copyright 2023 Postern Publishing. All Rights Reserved.

Scroll To Top