The delightful little Eastern Shore town of St. Michaels, MD has a slogan depicting it as, “the town that fooled the British.” During the War of 1812, town citizens, forewarned that British ships were approaching, hoisted lanterns into the tall trees above the houses and shipyards, causing the British to overshoot their targets with cannon fire. Only one house was hit, and the town escaped destruction.

Present-day St. Michaels isn’t all that remiss from what it looked must have looked like during this fabled part of Eastern Shore history. The center of town, St. Mary’s Square, sits on land purchased and divided in 1778. The houses on the square are built close together and are almost miniature, dollhouse-like structures with architectural appointments conjuring craftsmanship from a time long ago. This part of town is particularly magical—a time capsule of sorts that’s made all the more special during the holiday season.

Christmas in St. Michaels is a distinction given to the second weekend in December featuring the town’s Holiday Parade, festive dinners, choir concerts, a gingerbread decorating contest, a tour of homes, children’s activities, and more. For 26 years now, the proceeds from the ticketed events and the sale of the Collector’s Ornaments have raised more than one milion dollars for local non-profits.

If you visit St. Michaels during this festive 3-day weekend, beginning Friday, December 7th, you can expect to see the St. Michaels School Campus transformed into Santa’s Winter Wonderland, where children can enter Santa’s workshop and purchase presents for their families in secret, assisted by volunteer ‘elves.’

The Women’s Club of St. Michaels hosts a gingerbread house contest including elaborate entries from young and old alike, depicting various Eastern Shore scenes.  Crowds of visitors walk the streets, on their way to and from various historic homes—many dating back to the late 1700’s—with their festive doors open to the public as part of the holiday house tour. Everywhere one looks it’s festive old-fashioned merriment, as if stepping into a Currier and Ives print.

The St. Michael’s Museum on the Square showcases the town’s history—the buildings where Frederick Douglass once perused, what life was like in a fishing cottage from 1800, for example. Festive wreaths and greenery dress up the artifacts.  A near ladder-like set of stairs gives access to the second floor, which remains much like it did over 200 years ago. Working trains with actual smoke from the engines encircle a large tree in front, and take up an entire room of the museum, delighting children who chase the outdoor train, squealing with delight.

Just off the square, is the town’s shopping and commercial artery, Talbot Street. Yet just like every other aspect of the town, this heart of commerce is dressed beautifully, and made all the more impressive considering that St. Michaels has only begun to shift focus from ship building and seafood processing to tourism, in the past 30 years.

Locally owned businesses here all convey a large element of whimsy. Some express an understated charm—rooms are decorated with ancient antiques in such a way that the mind can’t help but wonder where these items once stood—perhaps beautiful manor houses abroad, or the large estates on the water that presently house the town’s more famous residents. Other shops’ wares literally spill out into the streets, beckoning patrons to enter and play with the toys, devour the sweet treats, or sit a spell in an atmosphere that feels as much like home as it does like something from a fairytale. That’s really the thing about St. Michaels—it manages to be the usually unattainable—creating an atmosphere that’s both comfortable and exceptional.

Luxury vehicles maneuver the narrow side streets once meant for nothing more than horse and carriage. Watermen mingle with statesmen, children are welcome in stores brandishing high-end merchandise, and all around it’s a profound sense of coming together for the season.

Christmas is a particularly enchanting season in St. Michaels, a town that already feels plucked from a storybook. The mixture of history, architecture, and current creative commerce conveys a European feel—a place where time marches on, taking the best of the past with it. If you happen to stay into the evening, you’ll hear the melodic sound of a church organ, filling the entire town with music and inviting those who leave to return again one day to this charming town on the water.

If You Go:

Christmas in St. Michaels December 7 – 9, 2012

Highlights of the weekend include:

More information can be found at Christmas in St. Michaels