Santa announces Chestertown arrival; Christmas parade set for Nov. 27

Santa will be giving the reindeer a night off Friday, Nov. Nov. 26 when he arrives in downtown, continuing his annual tradition of catching a ride with the Chestertown Volunteer Fire Company.

CHESTERTOWN — Chestertown’s holiday season officially kicks off on Friday evening, Nov. 26 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 p.m. and will visit with children in his house until 8 p.m. Hot chocolate will be available for purchase from the local Boy Scout troop.

The next day, Saturday, Nov. 27, 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, call Kristen Owen at 410-778-1600 or email

The parade assembles in the Chestertown Business Park, on Dixon Drive, and proceeds down High Street to Spring Street. Because the farmers and artisans markets will take place as usual in the 200 and 300 blocks of High Street, the public is encouraged to view the parade from upper High Street. The reviewing stand will be on the corner of Spring Avenue and High Street.

Santa will be in his Fountain Park house seeing children after the parade until 1 p.m. He will keep the same hours on the following Saturday, Dec. 4 during the Dickens of a Christmas weekend. H will be receiving children from 10 a.m. to 1 p.m. on Dec. 11, and Dec. 18. Children will receive gift bags from Santa courtesy of Twigs and Teacups.

From 9 a.m. to 5 p.m. Saturday, Nov. 27, the community celebrates Small Business Saturday with 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.

Santa’s Arrival and the Christmas Parade are hosted by Main Street Chestertown and Downtown Chestertown Association, and generously sponsored by local businesses and community members, including: Twigs and Teacups, Ye Olde Town Bocce League, Kent Cultural Alliance, the Imperial Hotel, Occasions Catering and Chester River Packet Co., Bad Alfred’s Distilling, Chesapeake Bank and Trust, Owen Excavation, Casa Carmen, Dukes-Moore Insurance, Shore to Be Fun, Figg’s Ordinary and Barbara Jorgenson and David Bowering.

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

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