Santa’s Arrival and Christmas Parade November 25-26


The Chestertown holiday season officially kicks off on Friday, November 25 at 6:45pm in Fountain Park when members of Kent County Community Marching Band herald Santa’s arrival by fire truck at 7:00pm. After he arrives, Santa will see children in his house until 8:00pm. Boy Scout Troop 130 will take pictures of children with Santa (donation encouraged), and will also selling hot chocolate in the park.

The Annual Kent County Christmas Parade takes place the following day, Saturday, November 26 at 10:00am (rain, snow or shine). This popular holiday event features marching bands, classic automobiles, various floats, Santa, Rudolph, Olaf, the Grinch and of course some of Santa’s trusty elves. Cash prizes will be awarded by parade judges to entrants in each category thanks to the support of Figg’s Ordinary, Chester River Wine & Cheese, Twigs & Teacups, Cassinelli Distilling and Spa Angels. Participation in the parade is open to everyone. If you are interested in participating, please call Kristen at 410-778-1600.

Santa will be in his Fountain Park house seeing children after the parade, from 11:00am to 1:00pm, and Kent County High School Music Boosters will be selling hot chocolate. Santa will also be available in his Fountain Park house on Saturdays December 3, 10 and 17 from 11:00am to 1:00pm. Children will receive gift bags from Santa courtesy of Dukes-Moore Insurance Agency and Garfield Center for the Arts.

Also on Saturday, November 26, celebrate Small Business Saturday by shopping in Downtown Chestertown. This nationwide event spotlighting local, independently owned shops and businesses provides an opportunity to reinvest your holiday shopping dollars in your local community and find some unique gifts, too. This year to celebrate Small Business Saturday, members of the Downtown Chestertown Association are offering a shopping passport, which provides discounts if you shop at participating businesses and also gives you the opportunity to win prizes if you collect multiple passport stamps.

Chestertown’s holiday festivities continue the following weekend, December 2, 3 and 4 with Winterfest Weekend. In its third year, Winterfest is a town wide celebration that kicks off with a special illuminated First Friday, and continues through the weekend with The Soroptimists’ Festival of Trees, a gingerbread workshop, the Chester River Chorale’s holiday concert and many more family friendly events and activities.

For more information about these holiday activities and other events and projects sponsored by Downtown Chestertown Association, please visit

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