Chestertown’s holiday season officially kicks off with Hometown Holiday on Friday evening, Nov. 25 as Santa presides over the Annual Kent County Holiday Parade, beginning at 5:30pm on High Street.

This popular holiday event features marching bands, classic automobiles, various floats, and familiar characters such as Rudolph, Olaf, and the Grinch. Parade judges will award cash prizes to entrants in each category. Participation in the parade is open to everyone. If you are interested in entering a float or group, please email kowen@mainstreetchestertown.org.

Santa is scheduled to arrive by fire truck at the end of the parade and will visit with children in his house in Fountain Park until 8:00 p.m. Boy Scout Troop 130 will take pictures of children with Santa (donation encouraged), and sell hot chocolate.

Santa will see children again on Saturday, Nov. 26 from 11am-1pm and then on the following Saturday, Dec. 3 during the Dickens of a Christmas weekend. He will also be receiving children from 11:00 a.m. until 1:00 p.m. on Dec. 10 and Dec. 17. Children will receive gift bags from Santa courtesy of Twigs and Teacups. For more information about holiday activities, visit mainstreetchestertown.org, email office@mainstreetchestertown.org, or call 410-778-2991.

Also on Saturday, Nov. 26, from 9 a.m. to 5 p.m., the community celebrates Small Business Saturday by shopping in Downtown Chestertown. This nationwide event spotlighting independently owned shops and businesses provides an opportunity to reinvest holiday shopping dollars in the local economy and find some unique gifts, too.

Hometown Holiday is hosted by Main Street Chestertown and the Downtown Chestertown Association. Main Street Historic Chestertown Inc. is a 501(c)3 non-profit organization which is dedicated to preserving, enhancing, and promoting historic downtown Chestertown. The Downtown Chestertown Association (DCA) is a non-profit organization dedicated to promoting businesses and professional services in and around Chestertown through activities that encourage residents and tourists to visit and shop locally.