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Fall Into St. Michaels 2019

October 19, 2019 - October 20, 2019

The change of the season brings excitement and vibrant color to the town, as residents and businesses celebrate Fall Into St. Michaels. This annual town-wide event is always a crowd pleaser.

This year’s festivities begin with the town-wide scarecrow contest starting on Saturday, October 19. Participating area businesses are competing in the Fourth Annual St. Michaels Scarecrow Contest, where each sponsoring business will have the chance to win first place in one of the following three categories: Traditional, Whimsical or Humorous and will seek the coveted People’s Choice award. The scarecrows will be displayed at the St. Michaels Community Center through Sunday, October 20. Visitors can vote for their favorites on Saturday and Sunday. Winners will be announced on the Visit St. Michaels website, www.stmichaelsmd.org, on November 1.

It’s also the Annual Pumpkin Carving Contest on Saturday, October 19, held at the St. Michaels Community Center, located at 103 Railroad Avenue. Participating businesses sponsor the pumpkins, which are carved by both experienced and novice carvers, each striving for the top spot in one of the four pumpkin categories. The pumpkin contest viewing is from 10:30 a.m. to 7 p.m. on Saturday (closed for visitors for about a half an hour from 1-1:30 p.m. for judging) and 10 a.m. through 2 p.m. on Sunday.

The Bay Hundred’s 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. Each contestant must submit two to three 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 a.m. and sales are from 10:30 a.m. to 7 p.m. Proceeds of the bake sale will benefit the programs and activities of the St. Michaels Community Center. Contact Trish at the SMCC 410-745-6073 for more information or to register as an entrant.

The St. Michaels Museum at St. Mary’s Square will offer walking tours. The walking tour is $10 per person and also includes admission to the museum. Visit www.stmichaelsmuseum.org for more information and to reserve a space.

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 are on Sunday, October 20 and will begin at 11 a.m. Registration is available at stmichaelsmd.org and at 10 a.m. the morning at the event. 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. Refreshments, including coffee, donuts and a Bloody Mary and Mimosa Bar, will be available on site. There will be live raffles of items from area restaurants and retailers between races. No Dog? No Problem – Fun for humans, too.

Visit www.stmichaelsmd.org or call 410.745.0411.


October 19, 2019
October 20, 2019


Downtown St. Michaels
St. Michaels, MD 21663 United States + Google Map
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Allison Rogers



Attraction Magazine

PO Box 360
Easton, MD 21601

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