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Taste of St. Michaels - Fall Tasting Crawl
November 8th | 11:00am-4:00pmDiscover the Flavors of St. Michaels at the Taste of St. Michaels Tasting Crawl!
Mark your calendars for Saturday, November 8th, and get ready to indulge in the finest culinary offerings of St. Michaels during the Taste of St. Michaels Fall Tasting Crawl! From 11:00 AM to 4:00 PM, our charming town transforms into a food lover’s paradise, featuring award-winning restaurants and Chesapeake Bay-inspired creations.
🌟 No Tickets Required
Enjoy a relaxed and sophisticated culinary journey—purchase tastings directly at each participating venue! With prices ranging from $1 to $5, this event offers an accessible way to sample the best of St. Michaels. Each stop will showcase a curated selection of elevated bites and beverages designed to delight your palate.👉 Learn more...
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Saturday, November 22 | 11am–5pm
The Eastern Shore Sea Glass & Coastal Arts Festival, celebrating it's Holiday Edition on Saturday, November 22, 2025 on the waterfront campus of the Chesapeake Bay Maritime Museum and offers fun for the whole family with fantastic shopping, great food and drinks, live music on two stages, and more. The popular celebration of all things coastal will run 10am–4pm on Saturday with all tickets valid for admission to the festival and the CBMM campus.
This Holiday Edition of the festival is set to highlight more than 60 exhibitors from across the country, selling an array of unique coastal and sea-glass related goods, including jewelry, home décor, art, and more.
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Midnight Madness 2025
Saturday, December 6th | 10am–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 15–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.
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