
A crowd of youngsters awaits as Santa dismounts from a Chestertown Volunteer Fire Company vehicle — photo by Peter Heck
Chestertown kicked off the Chrismas season with its annual parade, featuring marching units, floats, bands, and classic cars from all over the county — and even a few from across the river! Several hundred people lined High Street for the parade. with many of them staying afterward to meet Santa and give him their lists!

Spectators line High Street as the parade -and Frosty – come into view – photo by Peter Heck
All the kids’ favorite holiday characters were there — Frosty, Mr. Grinch, and of course, Rudolph the Red-nosed Reindeer. Many local organizations and businesses had floats in the parade, all with colorful winter and Christmas themes. Groups with floats included 4-H Clubs, Blue Bird Tavern, E.L.B. Incorporated, Garnet Elementary School, Kent County Humane Society, the Kent School, Sarah Paige Studio Salon, TalkieFiber, ThinkBig, and Ye Olde Town Bocce League. Cheerleaders from the Chestertown Christian Academy performed energetic acrobatics for the crowd. There were two–count-’em, two!– marching bands; the Kent County High School band and the Kent County Community Marching Band.
The Rough Riders were there riding beautiful horses. E.L.B. Inc. had reindeer on an elaborate sleigh that sprayed snow in its wake causing children on the sidewalk to run out in delight to capture the delicate flakes. The cast from the Garfield Theatre’s production of Annie, the Musical marched. One of the Chestertown fire trucks had a real live Dalmation dog riding on it. The climax of the parade was the arrival of Santa Claus on one of Chestertown’s own Volunteer Fire Company’s truck.
It was a hard task for the judges to pick winners from such a scintillating line-up! Kent County High School was the winning marching band. Chestertown Christian Academy won for best marching unit while Kent County 4-H won for best float. The 4-H entry was multi-part, with a motorized float followed by 4-H members leading ponies and dogs with one member on horseback. The Kent County Humane Society float also featured live dogs.
Below is a selection of Spy photos to help you get into the holiday spirit!

Blue Bird Tavern float in the 2019 Chestertown Christmas Parade — Photo by Peter Heck

E.L.B. Inc. float sprayed “snow” in the 2019 Chestertown Christmas Parade — Photo by Peter Heck

Mr. Grinch and Rudolf work the crowd – photo by Peter Heck

Students from Garnet Elementary School ride past the reviewing stand – photo by Peter Heck

Cheerleaders from Chestertown Christian Academy were recognized as Best Marching Unit – photo by Peter Heck

Santa greets spectators at parade’s end – photo by Peter Heck

Kent County Community Marching Band in the 2019 Chestertown Christmas Parade — Photo by Peter Heck

The Kent County High School “Bridgade of Blue” marching band won “Best Band” honors – photo by Peter Heck

The Kent County 4-H float won top honors – photo by Peter Heck

“Dickens of a Christmas” float features Victorian costume finery – photo by Peter Heck

4-H Float in the 2019 Chestertown Christmas Parade — Photo by Peter Heck

Cars in the 2019 Chestertown Christmas Parade — Photo by Peter Heck

Classic car in the 2019 Chestertown Christmas Parade — Photo by Peter Heck

Bocce League in the 2019 Chestertown Christmas Parade — Photo by Peter Heck
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Elizabeth Hill says
Thanks for the coverage. Kent 4-H will be in the Fountain Park this Saturday collecting toys as part of our 4-H Toy Drive, celebrating 20 years of collecting toys and gifts for Kent County Children. This is also our 10th year partnering with the Lions Clubs of Kent County and the Christmas Basket program. Thanks to all the community for 20 years of support!!!