• 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 a Taste of St. Michaels will take place during our Fall into St. Michaels weekend and includes a tasting crawl on Saturday, October 22, 2022 from 11 am - 4 pm.   The Tasting Crawl allows participants to taste their way around St. Michaels at award winning restaurants and other participating businesses in town, including lodging and shops around the Town of St. Michaels.

    Each tasting venue will have a tasting selections that feature food, drinks inspired by the Autumn season. 
    Each tasting will range from $1 to $5. 
    Participants will pay at the venues directly.   See venues and tasting information here.

    Fall into St. Michaels festivities begin with the town-wide scarecrow contest starting on Saturday, October 22, 2022 and continue throughout the weekend pumpkin carving contest from participating businesses and the Jack Russell Races on Sunday, October 23rd from 11 am - 1 pm at the St. Michaels Inn. 

    See photos of the 2022 Pumpkin Carving Contest here.


    Fall into St. Michaels Events

    •  Scarecrow Contest – Saturday, October 22 – Halloween, October 31 - Online Voting coming October 22
    •  Pumpkin Spice Run/Walk 5K - St. Michaels Running Company - 104 N. Talbot Street
      • Saturday, October 22  9am
    •  Pumpkin Carving Contest viewing – St. Luke’s United Methodist Church  304 S. Talbot Street
      •  Saturday, October 22 11am – 5pm
    • Jewelry Sale at St. Luke's Church
      • Saturday, October 22 12pm - 3pm 
    • Pumpkin Pie Contest - St. Luke’s United Methodist Church  304 S. Talbot Street   - See below for details on submitting entries
      • Saturday, October 22 10am – sell out    
    •  Fall into a Taste of St. Michaels – Throughout the Town at Participating Venues 
      • Saturday, October 22 11am  - 4 pm (or sell out)  
    • Jack Russell Races – St. Michaels Inn   - 1228 S. Talbot Street - See details below for entry form
      •  Sunday, October 23    10am Registration 11am Races start

  • The 2022 pumpkin pie and pumpkin carving contest was held at the St. Luke's Fellowship Hall for the Fall into St. Michaels on October 22, 2022.

    The pumpkin pie contest had Inn at Perry Cabin take first place, Josef's Cheesecake second and Ava's Pizzeria & Wine Bar took third place in the professional division. Jennifer Stevens took first place in the home baker division.

    There were over 300 people who vote for the coveted Pumpkin Carving Contest's People's Choice Award and the winner for 2022 is Cara from Ava's Pizzeria & Wine Bar with her amazing carved Octopus.
    Other pumpkin carving award placements:
    1st Place Chesapeake Trading Company
    2nd Place Ophiuroidea "The O" St Michaels, Maryland
    3rd Place The Galley

    1st Place Waterfront Restored & Renovated Hambleton Inn Bed & Breakfast
    2nd Place Brackish Life
    3rd Place The Crab Claw Restaurant

    Other Sponsors for the Pumpkin Contest:
    Foxy's Harbor Grille
    St Michaels Running Company
    Theo's St. Michaels
    Carpenter Street Saloon
    Simpatico - Italy's Finest
    The Christmas Shop

    Thanks to everyone who came out to support this amazing event.

    See photos of the Fall into St. Michaels pumpkins on our Facebook page here.

  • 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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