🎄✨ MIDNIGHT MADNESS IS THIS SATURDAY! ✨🎄
St. Michaels transforms into the most magical town on the Chesapeake this weekend — and you do not want to miss it.
Our shops, restaurants, and boutiques will sparkle with holiday lights, exclusive specials, live music, giveaways, and the kind of small-town Christmas charm you can only find right here in St. Michaels.
🍸 NEW THIS YEAR — The St. Michaels Holiday Cocktail Crawl!
Kick off the festivities early with our all-day holiday cocktail crawl, running 11 AM – 2 AM at participating bars and restaurants. Enjoy festive cocktails, spirited specials, and signature drinks crafted just for the season. Sip, stroll, and savor your way through town before the raffle begins!
🎁 The Famous Midnight Madness Raffle starts at 9:00 PM — with thousands of dollars in prizes from your favorite local businesses. And this year…
💥 The After-Party Continues! Bring your non-winning raffle tickets to participating shops after the drawing and redeem them for exclusive discounts and surprises. Every ticket still has value!
✨ Why You’ll Love Midnight Madness:
• Shops open late with festive treats & exclusive holiday specials
• Cocktail Crawl from 11 AM–2 AM with seasonal drinks & signature creations
• Live music, fire pits & magical photo moments
• Restaurants offering themed cocktails & late-night bites
• The small-town magic & energy you can only experience in St. Michaels
Grab your friends, bundle up, and celebrate the holidays with us in true Chesapeake style.
🌟 This Saturday. St. Michaels. Midnight Madness.
Holiday magic from morning ‘til midnight — and beyond.
Also check out other Music events in Saint Michaels, Entertainment events in Saint Michaels, Arts events in Saint Michaels.
