Hometown Holiday kicks off with parade and Santa’s arrival Nov. 24

CHESTERTOWN — The leftovers from Thanksgiving won’t be all gobbled up before the next holiday season will be upon us.

Santa and Mrs. Claus will arrive in Chestertown aboard a fire truck on Friday night, Nov. 24, saving the best for last in the annual Chestertown Holiday Parade.

The parade along High Street will step off at 5:30 p.m. as the kickoff to what is being billed as Hometown Holiday.

There will be marching bands,
classic automobiles, floats and familiar characters such as Rudolph, Olaf and the Grinch.

The top entries in various categories will be awarded cash prizes.

Participation in the parade is open to everyone. To find out how you can enter, email office@mainstreetchestertown.org.

Santa and Mrs. Claus will bring up the rear of the parade, their arrival announced by lights and sirens.

They will visit with children in the Santa House in Fountain Park until 8 p.m.

Boy Scouts of Troop 130 will take photographs of children with Santa (donation encouraged), and sell hot chocolate.

Santa will back in his house to visit with children from 11 a.m. to 1 p.m. Saturday, Nov. 25 and the following Saturday, Dec. 2 during the Dickens of a Christmas weekend.

He also will be available from 11 a.m. to 1 p.m. on Saturdays, Dec. 9 and Dec. 16.

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.

Small Business Saturday will be celebrated on Saturday, Nov. 25 from 9 a.m. to 5 p.m. in the downtown shopping area.

This is being held in conjunction with the nationwide event that spotlights independently owned shops and businesses. It 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 nonprofit that is dedicated to preserving, enhancing and promoting historic
downtown Chestertown.

According to its website, the Downtown Chestertown Association is a nonprofit “dedicated to promoting businesses and professional services in and around Chestertown through activities that encourage residents and tourists to visit and shop locally.” 

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