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Cars on High

Main Street Historic Chestertown, Inc. - Fountain Park

Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October.

Cars on High

Main Street Chestertown - Fountain Park

Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October.

Carnival On High

Downtown Chestertown Chestertown, MD, United States

Main Street Chestertown’s newest event… Carnival On High! Balloon animals, face painting, cotton candy, train rides, games & prizes! Mark your calendar, more updates to come! Food, drinks, beer & wine will be available for purchase!

Cars on High

300 High Street - Fountain Park

Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October.

Cars on High

300 High Street - Fountain Park

Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October.

Cars on High

300 High Street - Fountain Park

Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October.

Cars on High

300 High Street - Fountain Park

Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October.

Cars on High

300 High Street - 300 Block of High Street

Join Main Street Chestertown for Cars on High every third Thursday (April through October). Share your automotive beauty or come drool over someone else's! This event is free and open to the public.

Cars on High

300 High Street - 300 Block of High Street - 300 High Street - 300 Block of High Street

Join Main Street Chestertown for Cars on High every third Thursday (April through October). Share your automotive beauty or come drool over someone else's! This event is free and open to the public.

Carnival on High

Foot of High Street - - 100 High Street

The second annual Carnival on High will be held Saturday, July 1 from 5-8pm at the Foot of High Street. This year will include more face painters, more games, and a bubble performer. Bring the whole neighborhood and enjoy a summer favorite! This event is free and open to the public. All proceeds benefit Main… Continue Reading Carnival on High

Cars on High

300 High Street - 300 Block of High Street

Join Main Street Chestertown for Cars on High every third Thursday (April through October). Share your automotive beauty or come drool over someone else's! This event is free and open to the public.

Cars on High

300 High Street - 300 Block of High Street

Join Main Street Chestertown for Cars on High every third Thursday (April through October). Share your automotive beauty or come drool over someone else's! This event is free and open to the public.

Cars on High

300 High Street - 300 Block of High Street

Join Main Street Chestertown for Cars on High every third Thursday (April through October). Share your automotive beauty or come drool over someone else's! This event is free and open to the public.

Chestertown Car Show

Downtown Chestertown-Various - 300 Block of High Street

Your favorite annual car show is back! Enter your car to be judged or come view over 100 antique, classic, and modern cars on display in downtown Chestertown. Live band, food, and more. This event is free and open to the public. All proceeds benefit Main Street Chestertown.

Cars on High

300 High Street - 300 Block of High Street

Join Main Street Chestertown for Cars on High every third Thursday (April through October). Share your automotive beauty or come drool over someone else's! This event is free and open to the public.

Event Series Dickens of a Christmas 2023

Dickens of a Christmas 2023 – FRIDAY NIGHT (12/1) EVENTS CANCELED! WE WILL SEE YOU ON SATURDAY (12/2)!

Downtown Chestertown-Various - 200 Block of High Street

FRIDAY NIGHT (12/1) EVENTS CANCELED! WE WILL SEE YOU ON SATURDAY (12/2)! Kent County's favorite holiday event. Step back into 1840's London and experience the holiday season as Charles Dickens imagined it. This two day event includes carriage rides, entertainment, home tour, food, book talks, merchandise, and more. And don't forget to come dressed like… Continue Reading Dickens of a Christmas 2023 – FRIDAY NIGHT (12/1) EVENTS CANCELED! WE WILL SEE YOU ON SATURDAY (12/2)!

Chestertown Menorah Lighting

Fountain Park High Street, Chestertown, United States

Please join us for the Chestertown Menorah Lighting On the first night of Hanukkah Thursday, December 7 at Fountain Park. 5:30 PM Sponsored by Main Street Chestertown and The Chestertown Havurah Hanukkah is the Jewish festival commemorating the recovery of Jerusalem and rededication of the Holy Temple during the Jewish revolt against the ancient Greeks… Continue Reading Chestertown Menorah Lighting

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