Thousands of festival-goers line High Street to cheer the passing of colonial militia, marching bands, costume-garbed children and a variety of other participants in the festival’s parade. Boasting a colonial-theme, the parade prohibits automobiles and welcomes the horse-drawn carriage. It steps off at 10:00 am but arrive early to find a good spot.

If you are interested in becoming part of the parade, download and mail in the application or complete our online form. Email if you have any questions.


Please note the following:

  • Parade line up will begin at 9:00 a.m. on Saturday May 23, 2020 at the Chestertown Business Park (Dixon Drive and High Street).
  • Entries must have a colonial theme. Motorized vehicles are restricted.
  • Entries need to be in formation by 9:30 a.m. in order to participate.
  • There is a three-minute time limit at the judges’ stand–any group taking longer will be disqualified from judging.
  • Prizes will be awarded at the Judges’ Stand immediately following the flag raising ceremony at the completion of the parade.
  • Deadline for entries is Friday, May 15, 2020.