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HEY BOYS AND GIRLS! Santa Claus is putting safety first this year and limiting his pre-Christmas travel. He’s disappointed he won’t be able to visit Chestertown in person this year. It’s one of his favorite places to visit. The good news is, Santa (with help from his Elves) has scheduled time on two Saturdays, November 28 and December 5, to video chat with his Chestertown friends. He is looking forward to hearing about how good and kind you’ve been all year.

CLICK HERE TO SCHEDULE YOUR TIME WITH SANTA

FEATURES AND EVENTS

Lost in Chestertown: What Does An Out-of-Towner See On a Visit to Chestertown?

  Have you ever wondered how Chestertown looks to those who don’t live here? Lost in Chestertown is the first in a series of stories where Main Street Chestertown invites talented artists, photographers and writers from-away to share their visits through their own eyes. By 

CHESTERTOWN AL FRESCO DINING

Enjoy outdoor street dining on select Fridays and Saturdays while the weather lasts.

Photo by Caroline Phillips

Check out the latest one minute (give or take) videos from downtown Chestertown's shops and restaurants.

MAIN STREET CHESTERTOWN OFFERS
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CLICK FOR COVID-19 UPDATES AND SHOPPING INFO

MAIN STREET MINUTE