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December 12th-14th
Experience the magic of the holiday season in the heart of our charming waterfront town. For more than three decades, Christmas in St. Michaels has welcomed families and visitors from near and far to enjoy a weekend of festive cheer, small-town warmth, and unforgettable Eastern Shore traditions. Stroll along our decorated streets, shop local boutiques, savor seasonal treats, and enjoy beloved events such as the Holiday Parade, the Marketplace, and the Lighted Boat Parade gliding through the harbor.
Whether you’re discovering St. Michaels for the first time or returning for an annual tradition, Christmas in St. Michaels captures the spirit of the season—celebrating community, generosity, and the timeless beauty of our historic town.
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Saturday, December 6th | 11am–2am
🎄 Midnight Madness 2025 | Saturday, December 6th 🎄
The most magical night of the year returns to St. Michaels! ✨
Shop, sip, and celebrate all season long with raffle tickets earned on every purchase from November 21–December 6, leading up to the big gift basket drawing at 9PM at The Galley.
Enjoy the brand-new Christmas Cocktail Crawl, festive live music, photo ops, and an After Party throughout town where non-winning tickets turn into exclusive shopping and dining discounts.
Stay late. Shop local. Feel the magic of Midnight Madness in St. Michaels! 💫
#MidnightMadness2025 #StMichaelsMD #ShopLocal #ChristmasByTheBay
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Discover St. Michaels: A Coastal Escape with Charm & Adventure
Welcome to St. Michaels, a quaint waterfront town on Maryland’s Eastern Shore, recently named one of USA Today’s Top 10 Best Small Coastal Towns. Steeped in history dating back to the 1600s, this charming harbor town is home to the Chesapeake Bay Maritime Museum, where you can immerse yourself in maritime heritage while taking in breathtaking waterfront views.
Outdoor Adventures Await
Whether you’re looking to sail aboard a historic Skipjack, paddle through serene waters by kayak, bike along scenic trails, or perfect your swing on the golf course, St. Michaels is the perfect getaway for active explorers and relaxation seekers alike.Savor Every Bite
From cozy bistros and waterfront dining to the freshest seafood and award-winning crab cakes, St. Michaels is a foodie’s dream. Indulge in handcrafted cocktails, locally sourced dishes, and unforgettable flavors at the town’s top-rated restaurants.Shop & Stroll
Wander through the charming streets and explore an eclectic mix of boutique shops offering unique fashion, jewelry, home décor, specialty foods, and art galleries—perfect for finding that one-of-a-kind treasure.Stay in Style
Whether you’re looking for a romantic B&B, an award-winning inn, or a luxurious full-service hotel, St. Michaels offers a variety of accommodations to make your stay both comfortable and unforgettable.Come for the views, stay for the experience! Whether you’re planning a weekend escape, a girls’ getaway, or a solo retreat, St. Michaels is your perfect destination for relaxation, adventure, and a little bit of indulgence.
Plan your visit today! We can't wait to welcome you.
