This article is part of Jmore’s May/June 2021 Travel Issue featuring nearby getaways for the not-so-accidental tourist.
If you’re a sailor, I don’t need to tell you about Maryland’s Eastern Shore. But if like myself you’re more of a landlubber, you might think the towns of St. Michaels, Oxford and Easton are no more than highway signs on your way “downy ocean.”
That’s sooo not the case. Whether you’re daytrippin’ or looking for a few days away from home (and let’s face it, home sweet home just might not have quite the same appeal as it did pre-pandemic), the Eastern Shore is a year-round, picture-postcard destination and one of my favorite escapes.
The Chesapeake Bay village of St. Michaels makes a good home base for your visit with its abundance of unique accommodations (I’m partial to the Inn at Perry Cabin), restaurants, shops, attractions and proximity to towns like Easton and Oxford (which are both well worth a day trip or overnight stay themselves).
This compact, highly walkable town also is a mecca for history buffs. Once called Shipping Creek, St. Michaels dates from as early as 1632, and during the American Revolution became known as a shipbuilding center.
The shipbuilding industry ended here more than 150 years ago, but today St. Michaels is one of the best-known yachting centers on the East Coast and draws thousands of sailing enthusiasts annually.
St. Michaels is affectionately known as “the town that fooled the British.” Take a walking tour and your guide will tell you how in the early morning hours of Aug. 10, 1813, British barges planned to attack the town and a fort on the harbor side. Somehow forewarned, the town’s citizenry hoisted lanterns to the masts of ships and in the tops of the trees, tricking the British into overshooting the town.
Only one house was struck, with a cannonball penetrating the roof and rolling down the staircase as a Mrs. Merchant carried her infant daughter downstairs. Today known as the Cannonball House, it is still a private residence.
Among the many attractions in St. Michaels is the Chesapeake Bay Maritime Museum, with its lighthouse and exhibit buildings featuring boatbuilding, hunting, decoys, maritime art, steamboats and an aquarium. You can even sign up for a boatbuilding course on weekends and help the shipwrights construct an actual seaworthy vessel. For the best view in town, climb to the top of the Hooper Strait Lighthouse.
During warmer months, you can see St. Michaels from the water on half- or full-day boat trips. Year-round (weather permitting), see the town on land from a horse-drawn carriage.
For more Eastern Shore vibes, don’t miss a visit to the nearby towns of Oxford and Easton. Oxford, officially founded in 1683, is one of the oldest towns in the state and listed on the National Register of Historic Places.
Take a ride on the Oxford-Bellevue Ferry, said to be the oldest privately operated ferry in the country. Service began in 1683, was discontinued after the American Revolution, resumed in 1836 and has been in continuous operation ever since.
Established in 1710, Easton also is on my must-see Eastern Shore visits for its combination of history, architecture and the arts. The Avalon Theatre, built in 1921, is a wow with its Art Deco details, while the Academy Art Museum houses an impressive collection of modern American and European masters, and also hosts such events as the annual Waterfowl Festival, the Plein Air Competition and Arts Festival, the Chesapeake Film Festival and the Chesapeake Chamber Music Festival.
On my last visit to Easton, I was fascinated to take a walking tour of the neighborhood called The Hill. Founded in 1788, The Hill is one of the oldest free African-American neighborhoods in the nation still in existence today. Many African-Americans in Easton and Talbot County were free from slavery long before the Civil War ended, with free people of color living alongside white neighbors working as merchants, sailors, carpenters, midwives and farm laborers, to buy freedom for their relatives while pursuing equality and liberty for themselves. Descendants of some of those original residents still reside in the same homes today.
As life hopefully starts to return to a semblance of normalcy, you can keep tabs on what’s happening in the coming months for these destinations. If you’re not already captivated by Maryland’s Eastern Shore, one visit is all it will take to fall under its spell.
Carol Sorgen is a freelance writer and seasoned travel journalist.
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