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Your Weekend Guide to Chestertown
October 16 – October 18, 2026 · 8 events
This weekend in Chestertown, Maryland brings 8 live events across the city. 3 events are explicitly listed as free. Here's what's on.
Events in Chestertown This Sunday
1 event is listed for Sunday, including Fall into Place: October 2026 Gallery On View at Chestertown RiverArts. Events that start earlier in the weekend may still be running Sunday; open an event for its current schedule.
Thursday, October 15
Friday, October 16
Browse All Weekend Events
ChestertownMarylandThis Weekend
8 events
Frequently Asked Questions
- What's happening in Chestertown this weekend?
- There are 8 events happening in Chestertown this weekend (October 16 – October 18, 2026), including Art Adventures: Stitch and Share with Jasmine Sun at Chestertown RiverArts, Fall into Place: October 2026 Gallery On View at Chestertown RiverArts, Apple Fest at Kent County Public Library – Chestertown Branch, Richard O'Brien's The Rocky Horror Show at Garfield Center for the Arts at the Prince Theatre (8:00 PM). Browse the full lineup on VenuNite.
- Are there free things to do in Chestertown this weekend?
- Yes — 3 events in Chestertown this weekend are explicitly listed as free. Confirm current entry details on the event page or organizer source.
- What events are happening in Chestertown this Sunday?
- 1 listed events are happening in Chestertown this Sunday, including Fall into Place: October 2026 Gallery On View at Chestertown RiverArts.
- Where can I find things to do in Chestertown, Maryland?
- VenuNite aggregates live events from venues across Chestertown. Browse by date, venue, or event type to find what's happening near you.
