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Fall into St. Michaels

October 19 - October 20


Enjoy the beauty of the foliage color change in historic St. Michaels, Maryland. The change of the season brings excitement and vibrant color to the town, as residents and businesses celebrate Fall into St. Michaels. If you’re like us, you love the cool breezes, gorgeous sunsets and the perfect setting for a walk or bicycle ride.

Fall is 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.

Saturday, October 19 
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 20
The annual Jack Russell Races will take place on the lawn in front of the St. Michaels Inn.
10 am (registration) 11 am race start time


Stories of the Chesapeake