Midnight Madness in St. Michaels, Maryland

12/06/2025

Make sure to stop by Brackish Life for sweet treats!

12/06/2025

This is the best night ever!

Times ticking! 🍷🎁
Midnight Madness, Saturday, December 6th
Spend $25 at the winery and receive a raffle ticket for $1,000+ in local prizes.
🕘 Drawing at 9PM — be there to win! 🎉

12/05/2025

🎉✨ THE MIDNIGHT MADNESS AFTERPARTY CONTINUES! ✨🎉
After the 9 PM raffle drawing at The Galley, the fun is FAR from over!

💫 Redeem Your Non-Winning Tickets!
This year, your raffle tickets still have value even if your number isn’t called. Take your non-winning tickets to participating shops throughout St. Michaels and enjoy exclusive discounts, special offers, and unique late-night shopping experiences created just for Midnight Madness. Keep the excitement going and score amazing deals all over town!

🔥 THE AFTERPARTY AT The Preppy Redneck— 11 PM
Head over to the Preppy Redneck parking lot for the second big drawing of the night! At 11 PM, you’ll have another chance to win…
💵 $1,000 CASH!
Don’t miss your shot at the biggest prize of the evening.

🎄✨ TOMORROW IS THE NIGHT! ✨🎄
We can’t wait to welcome everyone to St. Michaels for what promises to be an incredible evening of holiday cheer, shopping, dining, giveaways, and unforgettable moments. With perfect weather on the way, it’s going to be a fantastic night filled with great deals and prizes for all.

See you TOMORROW for Midnight Madness!

Don’t miss out on The Preppy Rednecks midnight madness, thousand dollar raffle. 🎟️

Tickets can only be obtained at

One ticket for every $25 spent in store OR tickets can be purchased for $10 apiece

DRAWING is at 11pm - must be preset to win! 🩷 🐳

12/05/2025

🎄✨ TOMORROW IS MIDNIGHT MADNESS! ✨🎄
St. Michaels’ most magical day of the year is almost here — and you do NOT want to miss it!

Spend the day strolling our charming shops, enjoying festive food and drinks, and earning raffle tickets for the enormous Midnight Madness drawing happening at 9:00 PM at The Galley Restaurant!

🎁 BIG NEWS FOR 2025:
This year’s drawing will take place outside in The Galley’s back parking lot — giving us much more space, better views, and room for all the excitement. And guess what?
👉 We have 15 incredible gift baskets this year, packed with amazing prizes from your favorite St. Michaels businesses. The more you shop, the more chances you have to WIN!

🌤️ Weather Update:
Don’t let today’s snow fool you — tomorrow will be gorgeous! Perfect for shopping, dining, sipping, strolling, and soaking in all the Midnight Madness magic St. Michaels is famous for.

🏨 Hotels Still Have Rooms!
Make it a full weekend of holiday cheer. Some local inns still have availability — grab a room while you can!

🥂 Want the BEST Spot for the Raffle?
VIP seating is available at The Galley for the drawing. Limited seats remain!
Reserve here: https://us.orderspoon.com/thegalley

This is the night St. Michaels shines brightest. Bring your friends, bring your family, and come make memories on the most festive night of the year.

12/12/2024

2024 Recap…

✨ Midnight Madness: A Magical Night in St. Michaels ✨

Last weekend, St. Michaels came alive with the joy and wonder of Midnight Madness, and what a night it was! Our charming town sparkled under a canopy of holiday lights, as visitors and locals alike came together to celebrate the season in true Chesapeake Bay style.

🎁 Shopping Under the Stars: Our beloved boutiques stayed open late, offering one-of-a-kind treasures, holiday deals, and warm hospitality. Shoppers strolled the streets, sipping hot cocoa and finding the perfect gifts for loved ones.

🎄 Festive Cheer: From carolers filling the air with timeless melodies to the twinkle of Christmas lights reflecting off our historic storefronts, the town radiated with holiday magic.

🎉 Community Spirit: The raffle drawings brought excitement and smiles, as lucky winners walked away with incredible prizes generously donated by our local businesses.

🍷 Sips and Bites: Guests indulged in delicious food and seasonal drinks at our restaurants and cafés, creating a warm and inviting atmosphere that made the evening unforgettable.

Midnight Madness reminded us all of the magic of small-town charm during the holidays—a place where neighbors become friends and every moment feels special.

To all who joined us: Thank you for making this event such a memorable success! St. Michaels truly shines brightest when we come together as a community.


THANK YOU TO OUR AMAZING SPONSORS
Preston Automotive Group
Power Solutions
iFrog Digital Marketing
Safehouse

12/07/2024

🎉 Welcome to Midnight Madness! 🎉

We’re so excited to have you join us for the 23rd Annual Midnight Madness in St. Michaels! Get ready for a festive day and night filled with holiday spirit, amazing shopping, and incredible giveaways.

📍 Participating Stores and Restaurants: see list below!

✨ Don’t Miss the SPECIAL 13th Basket!
This year, we’re thrilled to offer an exclusive Weekend for Two Getaway in St. Michaels as our 13th basket prize! To enter:
1️⃣ Visit the RETAIL STORES on the list BELOW.
2️⃣ Look for the hidden QR codes in participating stores (not every store has one—it’s a scavenger hunt!).
3️⃣ Scan the QR code and enter your name, phone number, and email address.

Happy hunting and good luck! Make sure to explore all the stores and enjoy everything Midnight Madness has to offer.

🎄 Let the fun begin, and thank you for supporting our wonderful St. Michaels businesses!




The Shops at Sea Captain's Cottage
Olivins
Chesapeake Bay Outfitters
Chesapeake Trading Company
Come By Chance
american holiday
The Preppy Redneck
Skipjack's St. Michaels
Eat Sprout
BookHounds
St. Michaels Harbour Inn, Marina & Spa
Inn at Perry Cabin
The Old Brick Inn
Ava's Pizzeria & Wine Bar - St. Michaels
Theo's Steaks, Sides & Spirits - St. Michaels
Foxy's Harbor Grille
Gina's Cafe
San Miguels Mexican Foods
Simpatico - Italy's Finest
Ophiuroidea "The O" St Michaels, Maryland