• 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!     The scarecrow contest is held throughout town with winners announced November 1st.

    The annual Jack Russell Races on Sunday, October 20 will take place on the front lawn of the St. Michaels Inn located at 1228 S. Talbot St. St. Michaels, MD 21663.   

    Every year, dog owners from all over Maryland join the residents of St. Michaels 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 the St. Michaels Community Food Pantry and Pet Pantries 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!


    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.

    Saturday, October 19
    St. Michaels Community Center 

    ‚Äč103 Railroad Ave
    Pumpkin Pie Contest and Pumpkin Carving Contests

    Pumpkin contest viewing is Saturday from 10:30 a.m. - 7:00 p.m. (closed for visitors about 1/2 hour to hour at 1:00 pm for judging)

    Saturday viewing & purchasing pies begins  10:30 a.m. - 7:00 p.m.
    Sunday viewing of pumpkins 10:00 a.m. - 2:00 p.m.

    Sunday, October 20 
    Jack Russell Races

    St. Michaels Inn 

    1228 S Talbot Street St. Michaels, MD 21663

    10:00 a.m. (registration) 11:00 a.m. race start time


  • Before You Visit:

  • 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.

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