Ugly Sweater & Cookie Contest, Train Display & Jewelry Sale - Midnight Madness Event

New this year, the elves will put on a special event during the day from 1pm - 4pm at St. Luke's Church which will include a Cookie Contest & Bake Sale and Ugly Sweater Contest for humans and dogs!
There will also be a train display and jewelry sale at St. Luke's Church.

To register for Ugly Sweater Contest come to St. Luke's Fellowship Hall from 1pm - 2:30pm to register yourself or your dog. Contests will start after 2:30pm

To submit cookies for the Cookie Contest:
Bake and decorate 12 cookies to submit for the judging/contest 1pm -2pm

Midnight Madness Information:
Shop, Dine, Stay at participating businesses on Saturday, December 3rd to receive tickets for your chance to win amazing gift baskets.

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 years 21st Annual Midnight Madness event starts with the lighting of the Christmas Tree at St. Luke's Church on Friday, December 2nd. 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 raffle prizes valued at over $15,000. Look for Midnight Madness sponsor posters at your favorite shop, restaurant or lodging locations.

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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