Events & Happenings in Chestertown | #Chestertown https://stayhappening.com/chestertown-md Explore all events & things to do in Chestertown. Explore various shows, cultural activities, festivals or concerts happening in Chestertown. The full Events Calendar for the city. en Events & Happenings in Chestertown | #Chestertown https://stayhappening.com/assets/img/stay-happening.png https://stayhappening.com/chestertown-md <![CDATA[2026 Sultana Downrigging Festival Music Village Passes]]> 2026 Sultana Downrigging Festival Music Village Passes]]> <![CDATA[Grape Expectations: Brampton 1860 “Autumn in Full Swing: A Harvest Supper”]]> Grape Expectations: Brampton 1860 “Autumn in Full Swing: A Harvest Supper”]]> <![CDATA[Elegant Afternoon Tea at Brampton 1860]]> Elegant Afternoon Tea at Brampton 1860]]> <![CDATA[Autism Family Fun & Resource Day]]> Autism Family Fun & Resource Day]]> <![CDATA[2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (afternoon),2:30pm-5:00pm]]> 2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (afternoon),2:30pm-5:00pm]]> <![CDATA[2026 Downrigging Tall Ship Sails: SUNDAY NOV 1, 1:00pm-3:30pm]]> 2026 Downrigging Tall Ship Sails: SUNDAY NOV 1, 1:00pm-3:30pm]]> <![CDATA[Bat Chat & Guided Bat Walk]]> Bat Chat & Guided Bat Walk]]> <![CDATA[Bi-Monthly Bluegrass Jam]]> Bi-Monthly Bluegrass Jam]]> <![CDATA[Ink & Indie 2026 - Author Signing Event ]]> Ink & Indie 2026 - Author Signing Event ]]> <![CDATA[2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (morning), 10:30am-1:00pm]]> 2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (morning), 10:30am-1:00pm]]> <![CDATA[2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 2:30pm-5:00pm]]> 2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 2:30pm-5:00pm]]> <![CDATA[Waterfowl and Foliage Public Paddle - 2026- Sultana Education Foundation]]> Waterfowl and Foliage Public Paddle - 2026- Sultana Education Foundation]]> <![CDATA[Historic Chestertown Walking Tour]]> Historic Chestertown Walking Tour]]> <![CDATA[Kent County 911 Communications Center Tour]]> Kent County 911 Communications Center Tour]]> <![CDATA[Drawing Sultana]]> Drawing Sultana]]> <![CDATA[Chesapeake Bay 101-A 3 Part Series, Oct. 7, 14 & 21]]> Chesapeake Bay 101-A 3 Part Series, Oct. 7, 14 & 21]]> <![CDATA[Chestertown Book Launch and Author Signing]]> Chestertown Book Launch and Author Signing]]> <![CDATA[Understanding the story. Building Hope. Creating Connections.]]> Understanding the story. Building Hope. Creating Connections.]]> <![CDATA[Richard O'Brien's The Rocky Horror Show]]> Richard O'Brien's The Rocky Horror Show]]> <![CDATA[SAVE THE DATE Horizons Dance with the Stars]]> SAVE THE DATE Horizons Dance with the Stars]]> <![CDATA[The Crankies Show]]> The Crankies Show]]> <![CDATA[Ink & Indie 2026 - Author Signing Event]]> Ink & Indie 2026 - Author Signing Event]]> <![CDATA[Wisdom Through Horses™ A Journey for Women (5 Week Event Series) ]]> Wisdom Through Horses™ A Journey for Women (5 Week Event Series) ]]>