Loading Events

« All Events

  • This event has passed.

“Fall into St. Michaels” 2018

October 20, 2018 - October 21, 2018

October is a cause for celebration in St. Michaels when residents and businesses celebrate their annual harvest festival “Fall Into St. Michaels” on October 20 and 21.

The Fall Into St. Michaels festivities begin with the town-wide scarecrow contest starting on Saturday, October 20. Participating area businesses are competing in the 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 22.

And October 20 is also the start of the Annual Pumpkin Carving Contest held at the St. Michaels Community Center. 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. Pumpkin carving begins at 10 a.m. and judged from 1 to 1:30 p.m. They will remain on display until 7 p.m. on Saturday and again from 10 a.m. to 2 p.m. on Sunday at the community center.

The Bay Hundred’s Annual Pumpkin Pie Competition will be held during the Pumpkin Carving Contest at the St. Michaels Community Center. Slices of pie will be on sale after judging starting at 11 a.m. Proceeds of the bake sale will benefit the programs and activities of the St. Michaels Community Center. The St. Michaels Community Center is located on the corner of Railroad Street and Fremont Street.

Don’t miss out on the free children’s activities taking place at St. Luke’s Church, located at 304 South Talbot Street from 10 a.m. to 2 p.m. on Saturday, too.

The annual Jack Russell Races on Sunday, October 21 will take place on the front lawn at the St. Michaels Inn, located at 1228 South Talbot Street. Every year, dog owners from all over Maryland join the residents of St. Michaels for the Jack Russell Races. This year’s races will begin at 11 a.m. 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.

For all the details, visit www.stmichaelsmd.org or call 410-745-0411.


October 20, 2018
October 21, 2018


Downtown St. Michaels
St. Michaels, MD 21663 United States + Google Map
Get in Touch

Allison Rogers



Attraction Magazine

PO Box 360
Easton, MD 21601

The Good News Magazine
Serving the Eastern Shore for more than 40 Years!