Better Be Nice!

 Santa to Arrive in Chestertown Friday, Nov. 29

With Holiday Parade on Saturday, Nov. 30

Chestertown, Md., October 21, 2019—Chestertown’s holiday season officially kicks off on Friday evening, Nov. 29 as the Mayor turns on the holiday lights in Fountain Park and members of the Kent County Community Marching Band herald Santa’s arrival by fire truck.  The lighting ceremony is set for 6:30 p.m.

Santa is scheduled to arrive at 7:00 p.m. and will visit with children in his house until 8:00 p.m.  Hot beverages including hot chocolate, cider and mulled wine will be available for purchase.

The next day, Saturday, Nov. 30, Santa presides over the Annual Kent County Christmas Parade, beginning at 10:00 a.m. and filling High Street with 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 marching as a group, please call Kristen at 410-778-1600 or email

 The parade assembles in the Chestertown Business Park, on Lynchburg Street and Dixon Drive, and proceeds down High Street to Queen Street. Because Farmers Market artisans have been relocated into the 300 block of High Street while the grass reseeding in Fountain Park is underway, the public is encouraged to view the parade from above and below that area. The reviewing stand will be in the 200 block of High Street.

Santa will be in his Fountain Park house seeing children after the parade, from 11:00 a.m.  to 2:00 p.m. He will keep the same hours on the following Saturday, Dec. 7 during the Dickens of a Christmas weekend, then will be receiving children from 11:00 a.m. until 1:00 p.m. on Dec. 14, and Dec. 21.  Children will receive gift bags from Santa courtesy of Twigs and Teacups.

Also on Saturday, Nov. 30, 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.

For more information about holiday activities, visit the Main Street Chestertown Facebook page, email, or call 410-778-2991.