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October 17-19| 10am–4pm
Celebrate autumn on the Eastern Shore with Fall Into St. Michaels, a weekend packed with festive fun for the whole family.
🎃 Highlights include:
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Pumpkin Carving Contest at St. Luke’s Church
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Scarecrow Contest throughout town
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Wag-O-Ween
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Yappy Hour at Foxy’s
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Pumpkin Pie Baking Contest at the Community Center
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Martini Trail to crown the King of the Fall Martini
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Annual Jack Russell Races at the St. Michaels Inn
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Pumpkin Beer Garden at Foxy’s
…and so much more!
No tickets needed—just come and enjoy crisp fall weather, local flavors, and small-town charm. Dine, sip, shop, and explore St. Michaels this October!
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Saturday, October 25 | 10am–4pm
Get ready to celebrate the Bay’s favorite bivalve! The Chesapeake Bay Maritime Museum invites you to enjoy a day of food, music, and family fun at OysterFest 2025.
What’s on the Menu
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Fresh oysters prepared every way you love—raw, roasted, fried, and more
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Oyster offerings from the Talbot Watermen Association and local oyster farms
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The always-popular Oyster Stew Competition, where guests sample, sip, and vote for their favorites in a commemorative mug
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Chesapeake delicacies, local food vendors, craft beer, and specialty cocktails (available for purchase
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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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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.
