St. Michaels Maryland “The Town That Fooled the British”

By: Jacquie Roth

The historic town of St Michaels dates back to the mid-1600s, when it served as a trading post for area tobacco farmers and trappers. Located on Maryland’s Eastern Shore, St. Michaels is about halfway between the Susquehanna River and the mouth of the Chesapeake Bay. A tiny, well-preserved port, it’s become a destination for well-heeled Washingtonians as well as visitors from around the Bay and beyond.

During the War of 1812, St. Michaels gained its name as “the town that fooled the British.” Forewarned that British barges were positioned on the waters to attack with cannon fire, the residents hoisted lanterns into the trees above the city. This first successful “blackout” fooled the British into overshooting the town’s houses and shipyards. Only one house, forever since known as Cannonball House, was struck. 

Last April, I took part in the town’s annual and phenomenally popular WineFest. To say I had a wonderful time would be an understatement – the people, the food, the entertainment and of course, the wine selection were fantastic! I left St. Michaels knowing two things for sure: (1) WineFest would be a regular for every April to come, and (2) with so much culture, history and scenery to explore, a return visit during the quieter off-season was a priority. In January, I did just that.

Chesapeake Bay Maritime Museum – A Must See

Whether planning a day trip, weekend getaway or extended stay in St. Michaels, make it a point to visit the Chesapeake Bay Maritime Museum, located on Navy Point, where you can see a comprehensive collection of artifacts and exhibits that capture the history and beauty of the Chesapeake Bay. Here, you can learn about local naval history, watercraft and boat building traditions, seafood harvesting and the wide array of recreational activities along Maryland’s waterways. While on Navy Point, reserve a few minutes for photos of the historical Hooper Strait Lighthouse.

Shop, Shop, Shop

Hoping to bring a piece of the Chesapeake Bay with you as you depart St. Michaels? I found two favorite shops. The first is Ophiuroidea – better known in town as “The O.” Owned by local Maryland artisans Shella Kirchner and Kim Hannon, this fun shop features colorful, beach-themed artwork, accessories and furniture inspired by the coastal landscape. Among the many treasures that can be found here are Louise Taylor Crab Art. These collections of crab photography are pieced together to create dynamic “letter art,” capturing the essence of Maryland seafood in custom-made, historically rich tobacco stick frames. The second is Simpatico, offering a wide range of beautiful artisan products including foods and wines directly imported from Italy. Simpatico has an active list serve highlighting its own special events throughout the year.

Check-In and Stay for a While

There is no shortage of inns, cabins, resorts and quaint little bed and breakfast lodges that you can check into for a longer-than-a-day stay in St. Michaels. Two spots in particular have generated a lot of tourist “buzz” – the first being the Inn at Perry Cabin. This Victorian-inspired resort is known for its luxurious accommodations, fine dining, on-site recreational activities and full range of spa services. Many of its 78 rooms have fireplaces, designated living rooms and decks, patios or verandas.  Another hot spot to stay in town in the Parsonage Inn B&B, also known for its exquisite décor and amenities, and located within walking distance of the Chesapeake Bay Maritime Museum and many shops and restaurants. Those who have stayed here rave about the fresh muffins and pastries served each morning, as a “teaser” for the full hot breakfast that comes out shortly thereafter.

Oenophiles’ Paradise … Every April

WineFest 2013 will be held April 27 and 28, featuring hundreds of wines from 19 different venues. This year, the festival offers patrons tastings of new wines that are not yet available for sale in Maryland, as well as samplings from a variety of international winemakers. The popular “VIP Patriot Wine Tasting Cruise” is once again on the agenda, with an upgraded ticket option giving cruisers access to an additional wine tasting event in the courtyard area of The Old Brick Inn.

To plan your trip the easy way, visit

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