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Plan your trip early and stay in Chestertown! Click here for local lodging.

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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

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.

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