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

Present-day St. Michaels isn’t all that different from this fabled part of Eastern Shore history.  The center of town, St. Mary’s Square, dates back to the purchase of 20 acres and 58 deeded lots 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 a particular weekend in December featuring the Christmas Parade, festive dinners, choir concerts, and children’s activities.  The local high school transforms to 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 houses a gingerbread house contest including elaborate entries from young and old alike, depicting various Eastern Shore scenes.  A locally written book, The Santa Diaries, detailing Christmas memories from locals and signed by Santa himself, chronicles the town inhabitants’ fondness for the holiday season. 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 enlightens visitors to the town’s history—the buildings where Frederick Douglass once perused, what life was like in a fishing cottage from 1800.  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, sits 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 shop’s 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 of both comfort and exception.

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.

Outside of Simpatico, an importer of Italian wines, vinegars, oils, fabrics, pottery, and art, two men were shucking oysters fresh from the waters off St. Michaels—for nothing more than tips and conversation. This little scene is perhaps most indicative of St. Michaels. The mixing of it’s past as a seafood packaging town, and its present as a hub of tourism for those who travel from metropolitan areas across the Bay Bridge and from points east, to be immersed in the history of the town, and share in the bounties of food fresh from the water, and shop in the one-of-a-kind boutiques.       

Christmas is a particularly enchanted season in 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. In the evening, the sounds of something else chime, as if to solidify St. Michaels place in the world—the melodic sound of a church organ, filling the entire town with music and a palpable energy and calling to leaving visitors to return again one day to this charming town on the water.