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” on October 21 and 22.

The Fall into St. Michaels festivities begin with the town-wide scarecrow contest starting on Saturday, October 21. Participating area businesses are competing in the Second 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. Visitors can vote for their favorites Saturday and Sunday. Winners will be announced online at www.stmichaelsmd.org.

October 21 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 experienced and novice carvers alike, each striving for the top spot in one of the four pumpkin categories. The pumpkins are judged from 1 to 1:30 p.m. and then will remain on display until 7 p.m. on Saturday and again from 10 a.m. to 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 or 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 will begin at 11 a.m. Proceeds of the bake sale will benefit the programs and activities of the St. Michaels Community Center. Contact Trish at the SMCC at 410-745-6073 for more information or to register in the pie competition. The St. Michaels Community Center is located on the corner of Railroad Street and Fremont Street.

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

Every year, dog owners from all over Maryland join the residents of St. Michaels on the lawn at the Inn at Perry Cabin for the annual Jack Russell Races. This year’s races are on Sunday, October 22 starting at 11 a.m. Registration is available online at stmichaelsmd.org and at 10 a.m. that morning at the event. One may also register at St. Michaels Pet Supply, All Pets Veterinary Hospital and The Urban Pup. 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, as it’s fun for humans, too.

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