’Tis the Season in St. Michaels


Written by Katie Riley
Photography courtesy of Chesapeake Bay Maritime Museum and William Wilhelm Photography

Maryland’s Eastern Shore is home to many picturesque towns, but none embody an old-fashioned holiday feel quite like St. Michaels. With its quaint shops, world-class dining and jolly spirit, St. Michaels is transformed during the holidays into a Christmas wonderland.

Established in 1677 and named after the town’s Episcopal Church, St. Michaels is located on a long stretch of land, just past Easton, on the Miles River. St. Michaels has always been a destination for people looking to escape the noise and congestion of the city, with visitors as far back as the 1880s arriving via steamships to stay in summer cottages. But it wasn’t until the 1970s that tourism really took off as the maritime museum, boat tours and more hotels and inns were established. 

Today, St. Michaels is renowned as a weekend destination for the well-heeled crowd, who flock
to the posh Inn at Perry Cabin and enjoy fine dining at restaurants like Bistro St. Michaels, Theo’s and 208 Talbot. St. Michaels has also evolved into a family destination that offers history at the Chesapeake Bay Maritime Museum, boat trips with Patriot Cruises, bike rentals and family accommodations at resorts like the St. Michaels Harbour Inn, Marina & Spa. 

With the arrival of COVID-19 this past spring, the town was forced to close many businesses and began tentatively welcoming back visitors in late spring. With many Americans choosing local travel this year, St. Michaels proved itself a welcoming respite for travelers seeking a destination within driving distance. 

“All of the town’s businesses — restaurants, shops, hotels — worked really hard to establish precautions in order to welcome visitors back to St. Michaels,” said Kim Hannon, president of the St. Michaels Business Association. “It’s actually been a wonderful year for us, and we think that will continue through the holiday season.”

During the holidays, St. Michaels lives up to its reputation as a Norman Rockwellesque town bursting with holiday cheer. On Main Street, trees are lit with white lights, and large snowflake lights are hung on every post. Stores and restaurants are adorned with garland, wreaths and white lights, and an annual tree lighting the first weekend of December kicks off a monthlong celebration. 

The first weekend in December also features the annual Midnight Madness event, when the town’s stores are open until midnight and restaurants welcome shoppers with festive specials. Santa may be spotted strolling along Main Street, and Christmas music is played throughout the town. Shoppers who make a purchase during Midnight Madness are also entered to win a drawing for one of several gift baskets with merchandise worth up to $10,000. The town is still planning for Midnight Madness this year, opting to spread the event over three nights: December 3-5.

During the second weekend in December, “Christmas in St. Michaels,” a weekend-long celebration begins. While many events may be virtual, due to the pandemic, plenty of in-person activities are still happening, from dinner packages at the Inn at Perry Cabin to a “Light up the Night” drive-by house tour. On Saturday, December 12, the annual Lighted Boat Parade is scheduled to take place in St. Michaels harbor.

Innkeeper Will Workman, who owns and operates two inns in town, The George Brooks House and The Parsonage, expects to be busy through the holidays, despite the many changes this year. “We look forward to welcoming guests during the holidays,” Workman said. “Many travelers are looking for an escape that’s not too far from home. St. Michaels is a wonderful place to be during the season — it’s one of those towns that has Christmas written all over it.” 

For more information about Christmas in St. Michaels, visit stmichaelsmd.org.

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