21st Annual Midnight Madness
Saturday, December 3, 2022
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 year's 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).
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! See below for details on entering contests. There will also be a model train display and a 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
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!
2022 Midnight Madness Sponsors
The Midnight Madness Gift Basket Drawing will be held at The Galley Restaurant starting at 11pm!!
You must be there to win!
Shopping & Museums
Charisma Clothing Boutique
Chesapeake Bay Maritime Museum Store
Lat 38 Apparel & Gifts
Sea Captain's Cottage
St. Michaels Essentials
St. Michaels Running Co. (see special event info below)
Eating & Drinking
Eat Sprout (see special event info below)
Foxy's Harbor Grille (see special event info below)
Theo's Steaks, Sides and Spirits
St. Michaels Harbour Inn, Marina & Spa
St. Michaels, Tilghman and the Bay Hundred area have a wide range of lodging options to suit every taste and budget. Find the perfect place to fit your needs here.
Nothing says Chesapeake Bay like a steaming pile of locally caught Maryland blue crabs, and our restaurants are serving the Chesapeake Bay's bounty, from steamed crabs and crab cakes to sweet soft shell clams and fresh rockfish. Find the perfect restaurant here.
St. Michaels offers shopping galore, with an eclectic range of shops, including jewelry, clothing and home decor, galleries and more! Stop by one of the many tasting rooms, offering specialty foods and locally made libations. Find our unique shops here.
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.