• Fall into St Michaels
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  • Enjoy the beauty of the foliage color change in historic St. Michaels, Maryland.   The change of the season brings excitement and vibrant color to the town, as residents and businesses celebrate Fall into St. Michaels.  The cool breezes, beautiful sunsets and charming streets and views offer the perfect setting for strolling.
    Fall is the time when we yearn for snuggling in sweaters, we gear up for pumpkin patches and we sip on apple cider. The autumn months are a perfect time to visit St. Michaels for a romantic retreat or a family get away.

    The annual pumpkin carving and pie baking contest will be held in the St. Michaels Community Center on Railroad Avenue.   Stop by and vote for all your favorites, then grab a slice or two of pie, all proceeds benefit the St. Michaels Community Center!    

    Fall into St. Michaels could not happen without the support of the St. Michaels Business Association members, St. Michaels Community CenterTown of St. Michaels and Talbot County Office of Tourism.


  • Scarecrow Winners 2019

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      1st Place- Bistro St. Michaels
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      2nd Place- Ava's Pizzeria
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      3rd Place- Harbour Inn, Marina & Spa
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      Chesapeake Trading Company
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      Sea Captain's Cottage
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      Carpenter Street Saloon
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      Theo's Steakhouse
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      Lyon Distilling Company
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      Port Of Call Cigars
  • Pie Contest Winners

    Chef Category

    1st Place  Jason Hul-Miller- Theo's  Steakhouse

    2nd Place  Chef Pat, Jacob & Jennifer - Old Brick Inn

    3rd Place  Jason Hul-Miller - Theo's  Steakhouse


    Home Bakers Traditional

    1st Place Jen Stevens & Doug Stewart

    2nd Place Jo Batters

    3rd Place Sara Walker


    Home Bakers Creative

    1st Place Holly Evans

    2nd Place Lyndsey Pollock

    3rd Place Holly Evans

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  • 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.

  • 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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