Ring in the holidays in St. Michaels, as the historic, waterfront town transforms into a magical Christmas village during the holiday season, offering activities, shopping, and waterfront charm to make your festive visit unforgettable.
Christmas in St. Michaels
Photo credit: Richard Bodorff
The season’s signature event is Christmas in St. Michaels, which annually takes place the second weekend in December. For 2024, the 38th annual Christmas in St. Michaels is scheduled for Dec. 13-15 and is packed with festive activities, including parades, shopping, music, and the highly anticipated Tour of Homes. On Dec. 14, you can start and end your day with festive, holiday parades. The Talbot Street Parade kicks off at 10:30 a.m. Later in the day, turn to the Miles River for a view of the Lighted Boat Parade at 6 p.m. The parade can be seen from several locations within St. Michaels, including the campus of the Chesapeake Bay Maritime. Go early to explore the museum and enjoy Winter on the Chesapeake, which kicks off at noon with live music, food vendors, roaming carolers, and carriage rides.
Photo credit: Richard Bodorff
If you’ve ever wanted a glimpse inside some of St. Michaels historic homes, the Tour of Homes should not be missed. A stroll through St. Mary’s Square is also recommended, as you can marvel at the creativity of local bakers during the Gingerbread Competition and Display and shop for unique gifts at the Holiday Marketplace and Sweet Shoppe.
Midnight Madness
If your visit brings you to St. Michaels earlier in the month, you can take in the lighting of the town tree at St. Luke’s Church on Friday, Dec. 6 as the town transforms into a twinkling Christmas Village just in time for Midnight Madness. Shops along Talbot Street stay open late, offering refreshments, snacks, and great sales. Plus, each purchase from a participating business gives you a chance to win raffle prizes. On Saturday, stroll through a special holiday edition of the St. Michaels Farmers Market before returning to stores for more Midnight Madness shopping.
Magic – All Season Long
Photo credit: Richard Bodorff
The holiday season in St. Michaels is magical, and certainly worth a visit beyond the weekends of Christmas in St. Michaels or Midnight Madness. The town, businesses and private homes are beautifully decorated, making a breathtaking backdrop as you explore the area. Talbot Street, the town’s main shopping thoroughfare is lined with shops offering jewelry, home furnishings, housewares, and art. During this time of year, The Christmas Shoppe is a must-visit for unique holiday ornaments.
Warm up with a tasting at Lyon Rum, Eastern Shore Brewing, or St. Michaels Winery. Grab a bite from a great selection of restaurants. Foxy’s Harbor Grille allows you to soak in harbor views while enjoying fresh, locally inspired dishes. The Galley makes for a great brunch spot before a day of shopping. Freshly made pizza from Ava’s will take off the chill. While it may not be a traditional holiday drink, a margarita is good anytime of year and excellent ones can be found at both Gina’s and San Miguel Mexican Food.
St. Michaels lodging options are open year-round and make it easy to unwind and enjoy everything St. Michaels has to offer. If luxury is what you seek, the Inn at Perry Cabin offers stunning waterfront views along with festive décor. Beginning on Nov. 29, their entry drive is lighted for the season, creating a memorable scene for you to enjoy throughout the season. The Wildset Hotel will keep you right in heart of Talbot Street and their in room fireplaces will keep you nice and toasty this winter.
From quaint streets adorned with twinkling lights to signature events like Christmas in St. Michaels and Midnight Madness, St. Michaels is a must-visit holiday destination. Plan your visit and create lasting memories on Maryland’s Eastern Shore!
