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Downtown Chestertown – Fountain Park and nearby streets

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September 2019

First Annual Chestertown Car Show

September 14 @ 2:00 pm - 6:00 pm

The monthly Cars on High auto-enthusiast gatherings partners with Main Street Chestertown to create a downtown Car Show. Come admire a variety of vehicles from custom hotrods to classic and antique beauties. Category prizes, food and beverages, children's activities, and car-related contests will contribute to a fun afternoon that welcomes all. Event is free to the public. A modest registration fee is required for each car entered in the show. For information and to register, email:

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  • Mayor & Council Meetings: 1st & 3rd Mondays, 7:30 p.m.
  • Utilities Commission Meetings: 1st Mondays, 7:30 p.m.
  • Planning Commission Meetings: 3rd Wednesdays, 7:30 p.m.
  • Historic District Commission Meetings: 1st Wednesdays, 5:00 p.m.

TOWN TRASH & RECYCLING SERVICES The Town will be divided into two collection areas, both of which will be serviced twice each week. Collection of garbage and trash will be conducted in one area on Monday and Thursday evenings, and the other on Sunday and Wednesday evenings; except no collection will be made on New Years’ Day, Fourth of July, Labor Day, Thanksgiving Day or Christmas Day, but will be made on the next regular collection day after the holiday. Recycling: Paper, aluminum, household plastics picked up each Friday call 410-928-3333 (Infinity Recycling).