Chestertown, Rock Hall host holiday events this weekend

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 — While everyone finishes their Thanksgiving leftovers this weekend, the Main Street organizations for Chestertown and Rock Hall are kicking off the Christmas season with a slate of events.

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 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. He 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.

Rock Hall invites holiday shoppers to join in the fun with the “Merry Mascots” beginning on Small Business Saturday, Nov. 27.

According to a news release, participants will have chances to win $50 gift certificates to select Rock Hall businesses.

Mascot photo op cut-outs represent the following favorites: Great Blue Heron, Oyster, Rockfish, Eagle, Duck, Swan, Goose, Crab, Osprey and a Jellyfish. They will be located at, or around, local small businesses.

Simply take your picture with one of the “Merry Mascots” and post to social media. Be sure to include #RockHallMascots in your post.You may be the winner of one of the $50 gift certificates to Rock Hall businesses.

At least one winner will be drawn each week beginning on Saturday, Dec. 4 and ending on Saturday, Jan. 1.

Take advantage of this fun promotion by including Rock Hall as one of your holiday destinations for shopping, dining and getting to know a “Merry Mascot,” the release states.

This promotion is co-sponsored by Main Street Rock Hall and the Greater Rock Hall Business Association.

For more information about Chestertown’s holiday activities, visit the Main Street Chestertown Facebook page, email or call 410-778-2991. Visit and click on “Events” or email for more information about Rock Hall’s offerings.

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