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Plan your trip early and stay in Chestertown! Click here for local lodging.

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11th Annual Earth Day Festival

Downtown Chestertown

Celebrate our planet and sustainability at the11th Annual Earth Day Festival in Downtown Chestertown from 9am to 1 pm. FREE battery and fluorescent bulb recycling FREE paper shredding courtesy Chesapaeake Investment Advisors Trash Walks on Rail Trail & Downtown Electric Vehicle Car display Infinity Recycling "Guess the Bale Weight" Educational booths Want to participate in… Continue Reading 11th Annual Earth Day Festival

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Chestertown RiverArts Annual Paint the Town Plus

Downtown Chestertown

ENJOY A WEEKEND FESTIVAL OF OUTDOOR ART, IN THE OUTDOORS Chestertown RiverArts is putting a new twist on its annual Plein Air festival this year. On Friday and Saturday, June 4-5, come to historic Chestertown to enjoy Paint the Town Plus, a festive atmosphere celebrating the art of the outdoors in the outdoors. Works from… Continue Reading Chestertown RiverArts Annual Paint the Town Plus

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Juneteenth Celebration

Downtown Chestertown

Click on image to enlarge Juneteenth celebration: Friday June 18th, 2021 6-9pm Saturday June 19th, 2021 10am-8pm Sunday June 20th, 2021 11am-3pm The Black Union of Kent County and the Town of Chestertown Host Annual Juneteenth Celebration, June 14-19, 2021 On June 19, 1865, a group of formerly enslaved people celebrated the announcement of the… Continue Reading Juneteenth Celebration

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Crazy Days

Downtown Chestertown

Downtown Chestertown's Annual Sidewalk Sale! Fun For the Whole Family!! Bargains galore Restaurant specials Live Music Free Popcorn See Less

Chestertown Halloween Parade

Downtown Chestertown

Sponsored by the Chestertown Lions Club and Washington College SGA -Date of the event: Sat., October 30th at 10 a.m. --Rain date: next day (Sun) at 3 pm (to allow people to get out of church) -Handing out cash prizes totaling $355 dollars for six categories -The parade assembly area and starting point is Dixon… Continue Reading Chestertown Halloween Parade

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