ENJOY CHESTERTOWN'S YEAR-ROUND
Events Calendar
Upcoming Events
Whether you're a local or a visitor, our event calendar is brimming with engaging activities that cater to diverse interests. From lively festivals and captivating performances to informative workshops and delightful markets, there's always something for everyone. We can't wait to welcome you! Mark your calendars and join us for an event soon.
Hosting An Event?
Hosting an event you want to advertise to locals and visitors? Use the button to submit your event listing. For questions about events, contact Main Street at office@mainstreetchestertown.org.
October 2026
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Your Guide to Chestertown
Latest News
Spooky Season Arrives in Downtown Chestertown
Black Cat Art Trails, Scarecrows, Cult Classic Theater, and Tall Ships Pack the pre-Halloween Season.
$1 Rides and High Usage Mark Milestone First Year for Chestertown Community Bike Share
Marking a major milestone for local transportation, downtown vibrancy, and town connectivity, Main Street Chestertown is celebrating the one-year anniversary of its community Bike Share Program....
Bespoke Chocolate Opens With New Renovations
Things just got a whole lot sweeter in Downtown Chestertown! Bespoke Chocolate has officially opened the doors to its new, expanded location at 103 S. Cross Street, marking an exciting new chapter...