• Midnight Madness St Michaels
  • Midnight Madness

  • Midnight Madness St. Michaels 2020
  • 19th Annual Midnight Madness Thursday, December 3rd - Saturday, December 5th, 2020!

    Each year, the town of St Michaels is transformed into a picture perfect holiday postcard, the shops, restaurants and B&B’s are decorated with stunning greenery, lights and festive cheer.

    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.   

    2020 might be a little different, but that is not stopping our holiday spirit!   The Midnight Madness elves have worked hard to keep the tradition going, we hope you will join us as we celebrate Christmas in St. Michaels!




    19th Annual Midnight Madness in St. Michaels (Covid Style!) to be held Thursday, December 3rd - Saturday, December 5th, 2020

    Our commitment to keep everyone safe here.  

    Visiting St. Michaels during the holiday season is a special experience and provides a wonderful backdrop to shop for the holidays in our coastal harbor town as we celebrate Christmas in St. Michaels.   

    This year has proved to be a challenge, but the holiday spirit will continue with the annual Midnight Madness to be held Thursday, December 3rd through Saturday, December 5th, offering two more days of fun!   

    New for 2020 is the town wide Festival of Trees and the first “Grand Illumination” throughout the Town of St. Michaels on Friday at 6pm, when businesses and residents will simultaneously turn on their holiday lights & decorations as Christ Church bells ring Christmas carols.  

    The Midnight Madness elves have worked hard to keep the tradition alive while keeping in mind the welfare of businesses and visitors to make your experience safe and enjoyable.     The three-day event kicks off on Thursday, December 3rd with a special gift basket drawing for residents and visitors, and any non-winning raffle tickets will be entered for the big Saturday basket drawing.   


    As in previous years, Midnight Madness will have amazing gift baskets valued at over $10,000 donated from participating Midnight Madness sponsors.  This year we are distributing raffle tickets only during the event dates, from Thursday, December 3rd through Saturday, December 5th at 9pm.   Limited distribution and less tickets offers more opportunities to win amazing baskets filled with gift certificates and goodies!   

    During the three-day event shops will be open later with special sales all day and night.  Receive tickets with qualifying purchases for your chance to WIN AMAZING Gift Baskets while shopping, dining, and staying at participating sponsors hotels, B & B's and Inns.   As a bonus, stay at any participating lodging for two or more nights are receive 25 raffle tickets.   Shoppers will also receive raffle tickets for any carry out orders from participating restaurants and shop online from your favorite shops in St. Michaels to receive raffle tickets, too.  

    The Midnight Madness Virtual Gift Basket Drawing will be held on our Visit St. Michaels Facebook Page starting at 10pm!!  Winners will be notified via phone call starting at 10 pm so be sure to watch and wait for the call!


    Thanks to the many participating Midnight Madness sponsors and donations from businesses, Midnight Madness would not happen without them! 


  • 2020 Midnight Madness Sponsors 



  • 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.

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  • 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 wonderland.
    Read the article in the November/December Coastal Style Magazine here.

  • Special thanks to William Wilhelm Photography, the Town of St. Michaels and the Chesapeake Bay Maritime Museum for the use of their photos.

St. Michaels Maryland Business Association
 PO Box 1221, St. Michaels, MD 21663


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