Fall into St. Michaels

Welcome to Fall into St. Michaels, the time when we yearn for snuggling in sweaters, we gear up for pumpkin patches and we sip on apple cider. The autumn months are a perfect time to visit St. Michaels for a romantic retreat or a family get away.

The annual pumpkin carving, pie baking contest and scarecrow contest will be held in the St. Michaels Community Center on Railroad Avenue. Stop by at vote for all your favorites, then grab a slice or two of pie, all proceeds benefit the St. Michaels Community Center! On Saturday from 10:00 a.m. – 2:00 p.m. St. Luke’s United Methodist Church will have free Fall children’s activities.

The annual Jack Russell Races on Sunday, October 21 will take place on the lawn in from of the St. Michaels Inn.

Every year, 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 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 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!

Saturday, October 20
St. Michaels Community Center
​103 Railroad Ave
Pumpkin Pie Contest and Pumpkin Carving Contests

Pumpkin Carving is Saturday from 10:00 am to 7:00 pm (closed for visitors about 1/2 hour to hour at 1:00 pm for judging)

Saturday viewing 1:30 p.m. – 7:00 p.m.
Sunday viewing 10:00 a.m. – 2:00 p.m.

St. Luke’s Church
304 S. Talbot St
Free Fall children’s activities – 10am – 2pm

Sunday, October 21
Jack Russell Races
St. Michaels Inn
1228 S Talbot St, St Michaels, MD 21663
10am (registration) 11am race start time