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

Loading Events

« All Events

  • This event has passed.

Chestertown After Dark

July 27, 2018 @ 5:00 pm - 9:00 pm

Join us on Friday, July 27 for a night of crazy shopping deals, Eastern Shore wine and spirits, and live music in the Chestertown Arts & Entertainment district.
This is a night of amazing shopping and fabulous entertainment. Stores are opening their doors and offering deep discounts on the latest styles and trends in fashion, homeware, giftware, music, and crafts. Look for participating restaurants & stores along High St., Park Row, Cross St. and Cannon St.

Guests can enjoy wines by Crow Vineyard & Winery, Broken Spoke Winery, and St. Michaels Winery as they shop. We're also excited to host a special sprits tasting by Lyon Distilling Company. Chestertown's own, Bad Alfreds Distilling is serving up their local spirits all night long. You'll also find a special sampling of wines at Chestertown Natural Foods.

Figg's Ordinary, Bad Alfreds Distilling, The Kitchen and The Pub at The Imperial, and Chester River Wine & Cheese Co. along with #kentcountymd food trucks will keep you fed and happy.



  • 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).