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Main Street Chestertown


August 2020

al Fresco Restaurant Dining Downtown

August 22 @ 6:00 pm - 10:00 pm
|Recurring Event (See all)

One event on August 8, 2020 at 6:00 pm

One event on August 22, 2020 at 6:00 pm

Chestertown, MD 21620 United States

Chestertown al Fresco continues into August with three more opportunities to enjoy outdoor dining. The Kitchen at the Imperial and Casa Carmen will offer table service and live music, giving diners an opportunity to enjoy a meal under the stars with safe social distancing and other safety practices in place. The Kitchen will continue to serve meals in the 200 block of High Street, and Casa Carmen will serve in the 300 block of Cannon Street. Reservations are required for… Continue Reading al Fresco Restaurant Dining Downtown

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December 2020

CANCELLED – Dickens of a Christmas – Bah, Humbug!

December 4 - December 6

Bah Humbug! Main Street Chestertown Cancels 2020 “Dickens of a Christmas” Dickens of a Christmas is the Eastern Shore's only Dickens themed holiday festival. The fourth annual Dickens of a Christmas weekend kicks off during First Friday festivities throughout the Historic District, bringing carriage rides, hot beverages, fire pits, s’mores stations, and special entertainment to set the mood for a joyous holiday season.

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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.


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).

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