Christmas in Chestertown

Chestertown can be a truly magical place during the holidays! The holiday season kicks off just after Thanksgiving with the Christmas parade and Santa’s arrival. Santa maintains a “home” in fountain park where children can stop in and give him their wish list.

The “Dickens of a Christmas” Festival follows with a true Victorian feel throughout the town. Activities, vendors and just lots of fun! The stores are bright and cheery with Holiday music and gifts for everyone on your list…including yourself!

“Cookie Walks” abound at various churches and firehalls. A great opportunity to help local organizations while sampling some delicious cookies from local bakers. The Chestertown Volunteer Fire House and other local fire companies host craft shows where you can purchase handmade goods and support local artisans. The Soroptimists host the annual Festival of Trees, and Santa is there too!

You can always drive around after dark and see local homeowners decorate their homes for the holidays! This free light show is always lots of fun for everyone. Local Christmas pageants at the schools and churches and the Kent County High School hosts a free Christmas program at the planetarium.

Now in it’s 33rd year, the Planetarium Christmas Program is open to the public and offers seasonal refreshments and entertainment at no charge. The show is put together with the help of the staff and students of the high school’s FM radio station, WKHS-FM, 90.5, and it tells the story, traditions, and history of Christmas in our own special way.

On Christmas day, the annual “Feast of Love” Christmas dinner is held at First United Methodist Church from 1-4pm. This annual tradition began in 1984 and provides a free turkey dinner with all the trimmings, music and fellowship to anyone who would like to attend. In Chestertown, no one needs to spend the holiday alone…or hungry.

Come spend Christmas in Chestertown, and you might not want to leave!