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Midnight Madness -
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22nd Annual Midnight Madness Saturday, December 2, 2023 - Raffle Begins at 11pm at The Galley Restaurant
Shop, Dine, Stay at participating businesses to receive tickets for your chance to win amazing gift baskets.
Raffle tickets are being distributed by participating retail shops NOW through Saturday, December 2nd. All participating restaurants and lodging businesses will be distributing tickets on Friday, December 1st and Saturday, December 2nd.
Shopping on Saturday, December 2nd will be all day and all night, with most businesses staying open until at least 10:30pm. Raffle begins at 11 pm at The Galley and you will need to be there in person to win!
Celebrating the holidays in St. Michaels is a tradition for many, and this year is no different. Maryland’s Eastern Shore is home to many picturesque towns, but none embody an old-fashioned holiday feel quite like St. Michaels. With our quaint shops, world-class dining and jolly spirit, St. Michaels is transformed during the holidays into a Christmas Village. The holiday spirit is felt throughout town, which makes coming to St Michaels during the holiday season a special experience, year after year, and provides a wonderful backdrop to shop for the holidays.
This year's 22nd Annual Midnight Madness event starts with the lighting of the Christmas Tree at St. Luke's Church on Friday, December 1st. The tree lighting started in 2021 as a way to show support for the businesses in town and adorns ornaments representing the businesses. On the morning of Midnight Madness, start your day out with a brisk run or walk with St. Michaels Running Company's Holiday Hustle, a scenic 5k Run/Walk along St. Michaels Nature Trail (weather permitting).As day turns to night, St. Michaels becomes a beautiful twinkling Christmas Village. Shops will be open late with refreshments and snacks, and special sales during Midnight Madness, plus each purchase at participating businesses gives you a chance to win gift baskets!
Look for Midnight Madness sponsor posters at your favorite shop, restaurant or lodging locations.
Midnight Madness kicks off at The Galley at 9pm with Musician/DJ Bobby Reed, who will be singing songs, playing favorite holiday tunes and will have audience participation until the drawings start at 11pm.
Drawings start at 11:00pm at The Galley Restaurant and participants must be present to win.Thanks to the many participating Midnight Madness sponsors and donations from businesses, Midnight Madness would not happen without them!
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Stay Your Way: Dreamy Stays in St. Michaels & Beyond
Whether you’re planning a romantic retreat, a girls’ getaway, or a solo escape, St. Michaels, Tilghman, and the Bay Hundred area offer a chic and cozy mix of lodging options for every style and budget.
From boutique inns and charming B&Bs to waterfront resorts and private cottage rentals, you’ll find the perfect place to relax, recharge, and wake up to stunning Chesapeake Bay views.
Your dream getaway starts here—book your perfect stay today!
Find the perfect place to fit your needs here.
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Savor the Flavors of St. Michaels: A Foodie’s Paradise
Nothing says Chesapeake Bay vibes like cracking into a steaming pile of locally caught Maryland blue crabs, but that’s just the beginning! St. Michaels is home to an incredible culinary scene that goes beyond seafood—offering something delicious for every craving.
Seafood & Chesapeake Classics
From perfectly seasoned steamed crabs and golden, lump-filled crab cakes to sweet soft-shell clams and fresh rockfish, our waterfront town is a seafood lover’s dream.A World of Flavor
Craving something else? We’ve got it! St. Michaels serves up an eclectic mix of dining options, including:
Steakhouses for the ultimate indulgence
Authentic Mexican bursting with bold flavors
Classic Italian with homemade pasta & rich sauces
Greek & Mediterranean favorites like gyros, fresh seafood, and vibrant mezze platesFind Your Perfect Spot
Whether you’re looking for a romantic waterfront dinner, a lively crab feast, or a cozy spot for cocktails & small plates, St. Michaels has a table waiting for you. Explore our incredible restaurants here!Find the perfect restaurant here.
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Shop, Sip & Stroll: A Boutique Lover’s Dream in St. Michaels
Calling all trendsetters, treasure hunters, and boutique lovers—St. Michaels is your ultimate shopping destination! Wander through our charming, walkable streets and explore a carefully curated mix of stylish fashion, artisan jewelry, home décor, and unique finds you won’t see anywhere else.
Chic Boutiques & One-of-a-Kind Finds
From boho-inspired clothing and handcrafted accessories to coastal home décor and locally made art, our shops are full of pieces that tell a story—just like your next adventure.Sip While You Shop
Take a break at one of our local tasting rooms, where you can indulge in small-batch wines, craft cocktails, and gourmet bites—the perfect pairing for a girls’ getaway or a solo shopping spree.Ready to Discover Your Next Favorite Spot?
Explore our unique shops and boutiques right here in St. Michaels—where every corner holds something special. Come shop, sip, and stay a while!Find our unique shops here.
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Whether you're an experienced kayaker, a day-tripping boater, a sailing novice, a history buff, an avid fisherman, or anyone else who yearns to spend some time on the water, you will find something to do in St. Michaels and Tilghman Island. It's time to get out on the water and enjoy the outdoors! Find your boating options here.
