Events and Things to Do in Chestertown, MD

Sunday, November 15

Featured

Kent School Admission Open House

NOV

15

2:00 PM

6788 Wilkins Ln, Chestertown, MD

Learn more about Kent School's Preschool through grade 8 program. Meet students, teachers, administrators. Tour classrooms and...

Share

Thursday, November 12

• Connect with the Veterans Health & Wellness Foundation

  3:00 pm

  Kent County Public Library – Chestertown Branch, 408 High Street, Chestertown

  
  

Friday, November 13

• Toddler Time-Oh Deer!

  10:00 am

  Sultana’s Holt Center, 200 S. Cross Street, Chestertown

  
  
• Fall into Place: October 2026 Gallery On View

  12:00 pm

  Chestertown RiverArts, 343 High Street, Chestertown

  
  

Saturday, November 14

• Horizons Dance with the Stars - A Night in the Enchanted Forest - Save the Date

  Location Brittland Manor 211 Britland Fam Lane Chestertown, MD 21620 211 Britland Farm Lane Chestertown MD 21620, 211 Britland Farm Lane, Chestertown

  
  
• Chestertown Recycling Booth

  9:00 am

  Chestertown

  
  
• Fall into Place: October 2026 Gallery On View

  12:00 pm

  Chestertown RiverArts, 343 High Street, Chestertown

  
  
• Celebrate Life on the Moon with Matthew Swanson and Robbi Behr

  2:00 pm

  Kent County Public Library – Chestertown Branch, 408 High Street, Chestertown

  
  
• Horizons Dance with the Stars - A Night in the Enchanted Forest

  5:00 pm

  Brittland Manor, 211 Britland Farm Ln., Chestertown

  
  

Sunday, November 15

• Kent School Admission Open House 2:00 pm

  6788 Wilkins Ln, Chestertown

  
  

Friday, December 4

• Annapolis Holiday Market 11:00 am

  2040 Annapolis Mall Rd, Annapolis, MD, 21401