3rd Annual Chestertown Car Show October 1

Chestertown is known for its history, art scene, and entertainment, and now thanks to Jon and Barbara Slocum, it’s gaining attention for its collection of amazing cars! Jon and Barbara partnered with Main Street Chestertown and started Cars on High in downtown Chestertown several years ago to provide car lovers and enthusiasts one night a month to showcase their vehicles and talk “cars”. This event, held the third Thursday of each month (April-October), brings dozens of cars to the 300 block of High Street where passersby can view the cars, ask questions, and marvel at feats of automotive prowess.

Cars on High became so popular that in September of 2019, the Slocums and Main Street Chestertown hosted the first Annual Chestertown Car Show. The Show featured over 75 cars in 10 different categories, activities, and more. Prizes were awarded by town notables and car fever in Chestertown was born. This year, it’s back for its 3rd annual on October 1, 2022! The Show will run from 2-6pm, with a rain date of October 2. This year there will be over 100 cars, including a collection of Porsches, food and beverages, and music by Best Kept Soul.

“The Annual Car Show really highlights downtown Chestertown to be the perfect place to display the many cars hidden in garages in our area, and build the local car culture.” says Jon Slocum.

It’s not too late to register your car for this year’s show and be part of the fun. Registration is $20 online or $25 at the door the day of the show. For more information or to register, visit ChestertownCarShow.com. Entry to see the cars is free and family friendly. All proceeds benefit Main Street Chestertown and its work in Chestertown.

Main Street Historic Chestertown Inc. is a 501(c)3 non-profit organization which is dedicated to preserving, enhancing, and promoting historic downtown Chestertown, Maryland.