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            • Fall Into St. Michaels. 2025 Fall Into St. Michaels. 2025

              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:

              • Pumpkin Carving Contest at St. Luke’s Church

              • Scarecrow Contest throughout town

              • Wag-O-Ween

              • Yappy Hour at Foxy’s

              • Pumpkin Pie Baking Contest at the Community Center

              • Martini Trail to crown the King of the Fall Martini

              • Annual Jack Russell Races at the St. Michaels Inn

              • 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!

              Learn More...

            • OysterFest 2025 at CBMM OysterFest 2025 at CBMM

              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

              • Fresh oysters prepared every way you love—raw, roasted, fried, and more

              • Oyster offerings from the Talbot Watermen Association and local oyster farms

              • The always-popular Oyster Stew Competition, where guests sample, sip, and vote for their favorites in a commemorative mug

              • Chesapeake delicacies, local food vendors, craft beer, and specialty cocktails (available for purchase

              Learn More...

            • Taste of St. Michaels - Fall Crawl Taste of St. Michaels - Fall Crawl

              Taste of St. Michaels - Fall Tasting Crawl
              November 8th | 11:00am-4:00pm

              Discover 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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            • 🍁🍸 Fall Into St. Michaels: Crown the King of the Fall Martini! 🍸🍁

              Get ready to sip your way through St. Michaels’ most spirited weekend yet! During Fall Into St. Michaels, take the Martini Trail and taste your way through town as our local restaurants shake, stir, and compete for the title of King of the Fall Martini 👑

              From Friday, October 17 through Sunday, October 19, you can sample each restaurant’s signature fall-inspired martini and cast your vote online using the link provided at every stop. Your taste buds decide the winner!

              🍂 Participating locations include:
              Crab Claw • Corah's Corner • Ruse • Gina’s • Foxy’s • The Bistro • Ava’s • Theo’s • The Galley • C Street • Carpenter Street Saloon • Harrison’s • Olive Branch

              ✨ With so many fall flavors swirling around town — from spiced, pumpkin, and caramel creations to unexpected twists — this is one trail you don’t want to miss.

              🎉 There’s a full weekend of fun during Fall Into St. Michaels, but let’s be honest… this might just be the most delicious competition of them all.

              Learn More Here: Crown the King of the Fall Martini

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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.