• Fall into St Michaels
  • Fall into St. Michaels October 22-23, 2022

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  • The change of the season brings excitement and vibrant color to the Town of St. Michaels, as residents and businesses celebrate their annual harvest festival “Fall into St. Michaels”.    The change of the season brings excitement and vibrant color to the town, as residents and businesses celebrate Fall into St. Michaels.  Enjoy our fabulous restaurants, charming boutiques and galleries, or take a boat ride out on the water for some local history and sights.    Stay in our inns and B & B's for some much needed relaxation. The autumn months are a perfect time to visit St. Michaels for a romantic retreat or a family get away. 

    Fall into St. Michaels festivities begin with the town-wide scarecrow contest starting on Saturday, October 22, 2022. 


    Pumpkin Contest Winners, Congrats and thank you sponsors and carvers in 2021.   See photos of the contest and pumpkins here.




    First Place & People's Choice Winner - St. Michaels Crab and Steak House-   Hot Tub, corn hole pumpkin

    Second Place  The Christmas Shop    Bat

    Third Place    The Preppy Redneck     Baby Yoda




    First Place   St. Michaels Running Company  ( Shawn and family first time carving and taking first place, way to go!)     Drunk Pumpkin

    Second Place  Simpatico    Pinocchio 

    Third Place  Hopkins Original Art Gallery     Covid Busters



    First Place  Foxy's    Trailer and camp site

    Second Place  The Galley      Scary Fish

    Third Place   Ophiuroidea    Flower Hair

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  • Dog owners from all over Maryland join the residents of St. Michaels on Sunday on the lawn at the St. Michaels Inn for the annual Jack Russell Races. This year’s races will begin at 11:00 am. Registration is available online and at 10 a.m. that morning.  The proceeds from the benefit will go to St. Michaels Community Food Bank and Humane of Talbot, Caroline and Dorchester Counties.

    The races will be broken down into categories: Jack Russell, Dachshund Dash and the famous “So Your Dog Thinks He’s a Jack” race. All dogs are welcome at the event, big or small, racing or not, to mingle with other dog lovers in Talbot County. Dogs under 25 pounds are welcome to race.

    The event will be held, rain or shine! Refreshments, including Coffee & Donuts and a Bloody Mary & Mimosa Bar, will be available on site. There will be live raffles of items from area restaurants and retailers between races! Registration can be made ahead of time or at the event.   Mimosas and Bloody Mary bar will be available, as well as a great time watching the races.  The Jack Russell races will not happen if there is inclement weather. 


  • Upcoming Events

  • 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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