Fall into St. Michaels festivities begin with the town-wide scarecrow contest starting on Saturday, October 16, 2021. Participating businesses will compete in the Scarecrow Contest, where each business will have the chance to win in one of the following three categories: Traditional, Whimsical or Humorous.

The following weekend, October 23rd thru October 24th the Fall into St. Michaels festivities go into full swing on Saturday, October 22nd with the return of the highly anticipated Pumpkin Carving contest will return where participating St. Michaels Business Association businesses will sponsor the pumpkins, which are carved by experienced and novice carvers alike, each striving for the top spot in one of the pumpkin categories.  The pumpkin carving will be held at the St. Michaels Community Center on Saturday, October 23rd starting at 10:00am.  Judging takes place 1:00pm - 1:30pm and then the pumpkins will remain on display until 6:00pm on Saturday and 10:00am thru 2:00pm on Sunday.  Winners for scarecrow and pumpkin contests will be announced on www.stmichaelsmd.org 

The St. Michaels Community Center Annual Pumpkin Pie Competition will be held during the Pumpkin Carving Contest at the St. Michaels Community Center. The Pumpkin Pie Competition is open to professionals, home bakers and children. Each group will be judged on traditional or creative creations. Cash prizes will be awarded to top three winners in each category, and of course, bragging rights and a plaque go to the winners. Participating bakers must submit 2 – 3 pies of the same recipe.  The St. Michaels Community Center will be selling pieces and whole pies of those entered. Judging will begin at 10:00 am and sales will begin at 11:00am. Proceeds of the bake sale will benefit the programs and activities of the St. Michaels Community Center. Please contact the SMCC 410-745-6073 for more information or to register as an entrant. The St. Michaels Community Center is located on the corner of Railroad Street and Fremont Street.

The Galley Restaurant will host their first Pumpkin Pie Eating Contest on Saturday afternoon, visit their website to register here.

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. 

Register your dog. Hurry, spaces are limited - $25 per registration. Register your dog here>