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  • 🎉 WineFest at St. Michaels 2025 – A "Cellarbration" of 15 Years! 🍷

    Raise your glass—it’s time to celebrate 15 years of WineFest at St. Michaels! This signature event is back, bringing an unforgettable weekend of world-class wines, vibrant energy, and new experiences in the heart of our charming town. 

    📅 Mark Your Calendar!
    Enjoy multiple walkable venues across St. Michaels, each brimming with unique wine offerings and lively atmospheres. Plus, don’t miss our exciting VIP venue revamp—designed to elevate your WineFest experience!

    🍷 Curated Wines from Around the Globe!
    Embark on a journey of taste with wines from Wine Spectator’s Top 100, and selections from across the USA, Italy, France, Germany, Australia, New Zealand, South Africa, and beyond. Whether you’re a seasoned connoisseur or new to wine, you’re sure to discover a new favorite!

    🌍 Sip, Learn, and Savor

    • Engage with winemakers and wine experts.
    • Compare taste profiles and learn about production processes.
    • Enjoy exclusive WineFest pricing on all wines tasted during the event.

    If you’ve joined us before, you know the magic that awaits. If it’s your first time, prepare to immerse yourself in great tastings, wine education, and the thrill of discovering exceptional wines from across the globe.

    🍾 New Ticket Options for 2025!
    We’re introducing new ticket types to ensure everyone can enjoy the festivities in a way that suits them best.

    ⚠️ Important: This is an adults-only event. All attendees must be 21 or older.

    Gather your friends, make your plans, and join us for a weekend where wine is tasted, memories are made, and the spirit of St. Michaels shines bright. Let’s “cellarbrate” together!

    GET TICKETS HERE!

    #WineFestAtStMichaels #SipSavorCelebrate #StMichaelsEvents

  • Indulge in Sweet Bliss at the 7th Annual St. Michaels ChocolateFest! 🍫

    Get ready to treat your taste buds at the 7th Annual St. Michaels ChocolateFest! Mark your calendars for Saturday, March 8, 2025, and join us in celebrating all things chocolate in the charming town of St. Michaels.

    Highlights of the Event:

    🍫 Culinary Creations:
    Our talented local chefs will be crafting chocolate-inspired dishes and desserts that will delight your palate. From savory to sweet, these special menu items are sure to impress!

    🍫 The Chocolate Crawl:
    Embark on a delicious adventure throughout the town from 11:00 a.m. to 4:00 p.m. (or until items sell out). Participating businesses and restaurants will offer a variety of chocolate-themed tastings, artisan treats, desserts, and even wine, beer, and spirits to complement your chocolate indulgence.

    🍫 No Tickets Needed:
    This is a pay-as-you-go event—no advance tickets required! Bring cash, especially $1 and $5 bills, to purchase tastings directly from participating venues.

    🍫 Shop & Savor:
    While you stroll through town, explore local shops featuring unique chocolate items to take home and enjoy later.


    Crawl Tips for Sweet Success:

    1️⃣ Come Hungry! You won’t want to miss a single bite.
    2️⃣ Cash is King. Small bills make purchases quick and easy.
    3️⃣ Bring Friends & Family. Share the joy with loved ones!
    4️⃣ Dress for Comfort. Comfy shoes are a must for this rain-or-shine event.

  • Discover the Flavors of St. Michaels at the Taste of St. Michaels Tasting Crawl!

    Mark your calendars for Saturday, March 29th, and get ready to indulge in the finest culinary offerings of St. Michaels during the Taste of St. Michaels 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.

    🛍️ Beyond the Tasting Crawl
    St. Michaels isn’t just about the food—it’s a destination filled with charming shops, boutiques, and galleries where you can find unique treasures and handcrafted goods. Stroll through our historic streets and discover everything from local art and jewelry to specialty items that capture the heart of the Chesapeake.

    🏨 Stay the Weekend
    Make your visit unforgettable by staying overnight at one of our quaint bed-and-breakfasts or luxury boutique hotels. With cozy accommodations, exceptional service, and waterfront views, St. Michaels is the perfect place to relax and unwind after a day of delicious tastings.

    🗺 Tasting Map Coming Soon
    Plan your adventure with our Tasting Map, which will highlight all the exclusive stops and participating establishments. Stay tuned for updates!

    Rain or Shine
    This unforgettable experience takes place regardless of the weather, so grab your friends and family and prepare to explore the unique flavors and welcoming charm of St. Michaels.

    Join us for a day of exceptional cuisine, coastal inspiration, and small-town hospitality. Whether you’re sampling incredible dishes, shopping for one-of-a-kind finds, or enjoying a cozy stay, the Taste of St. Michaels Tasting Crawl offers a complete experience that celebrates the best of our town.

    We can’t wait to welcome you on March 29th! For more information, check back here or follow us on social media for updates. 🍴✨

  • About St. Michaels & the Bay Hundred Area

    St. Michaels is a picturesque harbor on Maryland's Eastern Shore and was named as one of the Top 10 Best Small Coastal Towns in America by USA Today.  Its harbor and some homes date back to the mid-1600's, and is home to the Chesapeake Bay Maritime Museum where you can immerse yourself in our maritime history.   

    The St. Michaels area is perfect for outdoor activities including sailing on historic Skipjacks, kayaking, golfing and bicycling.  St. Michaels is also known for exceptional restaurants, from quaint romantic bistros to waterfront restaurants, serving fresh seafood including the best tasting crab cakes!  For shoppers, you will find an eclectic range of boutique shops offering specialty foods, jewelry, clothing, home decor and art galleries throughout the town.  For overnight lodging, we have many small B&B's, award winning inns and full-service hotels to welcome you!

    Come and experience the beauty of St. Michaels and all this charming town has to offer!  See You soon!