Chestertown, MD · Latest Local Events

• 

  Dec

  5

  A Dark Victorian Christmas: Ghost Stories for the Longest Nights

  Dec 05, 2026 12:00 PM - 01:00 PM

  Kent Cultural Alliance

  USD 21
• 

  Dec

  5

  The Crankies Show

  Dec 05, 2026 01:00 PM - 03:00 PM

  Sultana's Holt Center

  Free
• 

  Dec

  5

  Dickens Holiday Home Tour

  Dec 05, 2026 10:00 AM - 03:00 PM

  The Bank

  49.87 USD
• 

  Dec

  5

  Dickens Victorian Tea

  Dec 05, 2026 01:00 PM - 03:00 PM

  Christ United Methodist Church

  61.60 USD
• Dec

  3

  Friends Holiday Wreath Making Workshop

  Dec 03, 2026 12:30 PM - 02:30 PM

  343 High St
• Nov

  7

  Bi-Monthly Bluegrass Jam

  Nov 07, 2026 01:00 PM - 03:00 PM

  Lawrence Wetlands Preserve

  Free
• Oct

  31

  Garnier-Thiebaut Fall & Holiday Trunk Show | Welcome Home Chestertown

  Oct 31, 2026 06:00 AM - 12:00 PM

  107 S. Cross Street
• Nov

  19

  Sustainable Farming

  Nov 19, 2026 06:00 PM - 08:00 PM

  Sultana's Holt Center

  Free
• Nov

  21

  Paint & Sip

  Nov 21, 2026 02:00 PM - 06:00 PM

  Sumner Hall

  65.87 USD
• Oct

  24

  Needle Felting Workshop! “Turkey” Chestertown, MD

  Oct 24, 2026 11:00 AM

  Lands Point Winery and Vineyards
• Nov

  7

  Botanical Blues: Cyanotype

  Nov 07, 2026 08:00 AM - 10:00 AM

  343 High St
• Nov

  15

  Dan Paisley & The Southern Grass

  Nov 14, 2026 07:00 PM - 09:00 PM

  Chestertown Volunteer Fire Co

  28.52 USD
• Oct

  15

  31 Nights: A Self-Portrait Series Experience (3 sessions)

  Oct 15, 2026 01:00 PM - Nov 20, 2026 03:00 PM

  Artist Michael Bell Studio & Workshops

  USD 425
• Nov

  8

  Learn to Play American MahJong-A 3 Part Series: Nov. 8, 15, 22

  Nov 08, 2026 11:00 AM - 02:00 PM

  Lawrence Wetlands Preserve

  Free
• Oct

  31

  2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (afternoon),2:30pm-5:00pm

  Oct 31, 2026 02:30 PM - 05:00 PM

  Chestertown Marina

  38.70 USD - 70.50 USD
• Nov

  7

  Reiki Level 1 Training with Fletcher Johnson

  Nov 07, 2026 07:00 AM - Nov 08, 2026 11:00 AM

  400 S Cross St
• Oct

  31

  2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (morning), 10:30am-1:00pm

  Oct 31, 2026 10:30 AM - 01:00 PM

  Chestertown Marina

  38.70 USD - 70.50 USD
• Oct

  10

  World Migratory Bird Day for Chestertown & Washington College

  Oct 10, 2026 07:45 AM - 11:00 AM

  Semans-Griswold Environmental Hall at Washington College

  Free
• Oct

  13

  Understanding the story. Building Hope. Creating Connections.

  Oct 13, 2026 06:00 PM - 08:00 PM

  Minary’s Dream Alliance

  Free
• Oct

  31

  Mobility, Stability & Soft Tissue Release with Leslie Pearlman & Denise Hopkins

  Oct 31, 2026 08:30 AM - 10:30 AM

  400 S. Cross St.