Fall Into St. Michaels 2023

Fall into St. Michaels weekend starts with our annual scarecrow and pumpkin carving contest with businesses around town participating.   The annual pumpkin pie contest is back this year to benefit the St. Michaels Community Center, and will be held Saturday, October 21st from 10am – 2pm at the Union United Methodist Church, located next to the community center.   Businesses and residents wishing to take part in the pumpkin pie contest should bring 3 pies to be judged and sold to benefit the SMCC on Saturday morning. There will also be pumpkin painting for children interested in participating.

New this year, the inaugural Wag-O-Ween, will be held at The Preppy Redneck’s back parking lot on Saturday, October 21 starting at noon.  There will be a dog costume contest, photos and a doggie trick-or treat at participating businesses, pick up your information at Wag-O-Ween Headquarters.   A kick off party will be held at Foxy’s Harbor Grill on Friday night from 4pm-6pm and again on Saturday from 12pm-3pm.

The Jack Russell races will return for a fun filled day for dogs and their owners.   It will be held Sunday, October 22nd at the St. Michaels Inn located at 1228 St. Michaels Rd, on the front lawn.   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.  To register click here.

This year’s event will feature a small vendor village including Coffee & Doughnuts and a Bloody Mary & Mimosa Bar. There will be a 50/50 raffle from local businesses, including gift cards to area restaurants, to benefit our local partners.  All proceeds from the benefit will go to local dog charities.