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Wandering Maryland’s Eastern Shore

Whether you’re attending the springtime Food and Wine Festival, the annual “Christmas in St. Michaels” celebration, or simply looking for a relaxing getaway, Maryland’s Eastern Shore is a year-round picture-postcard destination.

The pocket-sized Chesapeake Bay village of St. Michaels makes a good home base for your visit, with its abundance of unique accommodations, restaurants, shops, attractions, and proximity to towns like Easton and Oxford, well worth a day trip—or even overnight stay–themselves.

On my most recent visit to St. Michaels, I tried something different in terms of lodging. This time I stayed in a private home offered by Eastern Shore Vacation Rentals….and not just any home, but the one in which renowned author James Michener wrote his bestselling book, Chesapeake. Unfortunately, I didn’t whip out my own bestseller during my visit there, but the idyllic waterfront setting at the end of a scenic country lane inspired me to do something even more important—relax!

Though I was tempted not to leave my perch along the deckside hot tub, the charm of St. Michaels is hard to ignore. The streets of the compact, and highly walkable, town are lined with distinctive cottages and shops. Whether you’re in town for the Food and Wine Festival, as I was, or come back at a later date, there’s plenty else to see in this well-known shipping center.

Once called, in fact, Shipping Creek, St. Michaels dates from as early as 1632 and during the American Revolution became known as a noted 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 each year.

St. Michaels is also affectionately known as “the town that fooled the British.” In the early morning hours of August 10, 1813, British barges planned to attack the town and a fort on the harbor side. The residents of the tiny town, somehow forewarned, 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 –what else — the Cannonball House, it is still a private residence.

Among the many historic sites and visitors\’ attractions in St. Michaels is the Chesapeake Bay Maritime Museum, a waterfront museum with a lighthouse and eight 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 located at the Museum.

A walking tour of the historic city will take you past the Cannonball House, the Amelia Welby House, which dates from 1700, and St. Mary’s Square which houses the “Mechanics Bell,” which was cast in 1841 and rang at 7 a.m., noon, and 5 p.m. to measure the workday for the ships’ carpenters in the nearby harbor; also housed in the Square are the remains of a cannon used in the defense of the town during the War of 1812.

During warmer months, from May to October, 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.

Every year in December “Christmas in St. Michaels” transforms the picturesque Chesapeake Bay village into a Currier and Ives Christmas card brought to life. This year’s annual start to the holiday season begins on Friday, December 11, and lasts through the weekend.

When it comes to dining in St. Michaels, not surprisingly, seafood is on virtually every menu in town. At the Inn at Perry Cabin, Executive Chef Mark Salter has turned the Inn’s restaurant, Sherwood’s Landing, into one of the most “distinguished restaurants of North America” (if the weather’s nice, enjoy your meal on the patio). The Crab Claw Restaurant, open from March through early December, specializes in seafood and – you guessed it – crabs, with a spectacular harbor view. Another “distinguished restaurant of North America,” 208 Talbot, has a casual atmosphere with innovative cuisine, while Bistro St. Michaels is a recreation of a classic Parisian bistro. Shore Restaurant, located at the St. Michaels Harbour Inn Marina and Spa offers “contemporary, casual cuisine” that’s as beautiful to look at as it is to taste (don’t miss the Shore “S’mores” for dessert!). For a casual sit-down or takeaway meal, try the newly opened Market House Gourmet Grocer.

Chain stores haven’t hit St. Michaels yet, so this is a perfect spot to look for unique gifts. To get in the holiday mood, start at the Blue Swan Christmas Shop which has ornaments and gifts from around the world. St. Michaels abounds in antique shops (Canton Row Antiques has 12 dealers under one roof), nautically themed boutiques (Chesapeake Bay Maritime Museum Store), art galleries and cooperatives (Artiste Locale, Galerie Francaise, The Mind’s Eye Craft Collection, St. Michaels Hidden Artisans\’ Studio Co-op), and eclectic boutiques (Audrey Julian & Co., Chesapeake Trading Co., Coco & Company, and A Wish Called Wanda, where I bought a distinctive ring that has been drawing raves every time I wear it).

And finally, to complete your weekend of R&R, The Spa at Five Gables offers facials, massages, and herbal bath treatments to prime you for your return to the 21st century.


  • St. Michaels is situated on a peninsula between Tilghman Island, Easton, and Oxford on Maryland’s Eastern Shore, not far off Rte. 50. It’s a leisurely drive from Baltimore or Washington, or arrive by boat by sailing up the Miles River. For general information on St. Michaels, call (800) 808-7622 or visit www.stmichaelsmd.org.
  • For vacation home rentals, call Eastern Shore Vacation Rentals at 1-866-398-2722 or visit www.easternshorevacations.com.
  • For information on Christmas in St. Michaels, call (410) 745-0745 or visit www.stmichaelsmd.org/christmas.
  • Check in at www.stmichaelsfoodandwinefestival.com to find out more about the 2010 Food and Wine Festival, with celebrity guest chefs, cooking demonstrations, wine tastings (need an excuse to enjoy a glass of wine after breakfast…here it is!), and special menus at area restaurants.
  • Treat yourself to a spa service at the Five Gables Inn and Spa, 1-877-466-0100 www.fivegables.com.
  • For other lodging and dining options, The Inn at Perry Cabin can be reached at (800) 722-2949 or by visiting www.perrycabin.com. St. Michaels also has a number of B&Bs, as well as larger hotels such as the Harbourtowne Golf Resort & Conference Center (1-800- 446-9066, www.harbourtowne.com), and St. Michaels Harbour Inn and Marina (1-800-955-9001, www.harbourinn.com).
  • 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 Maryland and is listed on the National Registry 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! And if you need something to read while you’re in town, stop by Mystery Loves Company; this transplanted Baltimore store, owned by former librarian and mystery lover Kathy Harig, is “everything mysterious.” (410) 226-0010, or www.mysterylovescompany.com.
  • Historic Easton, established in 1710, is a treat for lovers of colonial architecture and beyond. Stop by the Avalon Theatre, built in 1921, with its Art Deco details, (410) 822-7299, or www.avalontheatre.com. The Avalon offers a well-rounded schedule of shows and events. For a taste of Northern Italy (not to worry, seafood is still available!), try Scossa Restaurant and Lounge, (410) 822-2202, or www.scossarestaurant.com.
Carol Sorgen Columnist, Writer, World Traveler

Carol Sorgen is a nationally recognized writer, editor, and public relations consultant. Her articles—on subjects as diverse as travel, health care, education, architecture, interior design, the arts, and business—appear in both print and on-line publications including The Washington Post, DC Style, Resort Living, The Baltimore Sun, European Homes & Gardens, Decorating Spaces, Chesapeake Home, WebMD, Baltimore Jewish Times and Washington Jewish Week…to name just a few.

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