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

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Kent County Chamber of Commerce Volunteer Fair

Downtown Chestertown-Various - 200 Block of High Street

The second annual Kent County Nonprofit Volunteer fair is an opportunity for community nonprofit organizations that use volunteers to display their function to the public in order to inform and attract new volunteers. The goal is to strengthen the ability of local service groups to meet the health, educational, and cultural needs in greater Kent… Continue Reading Kent County Chamber of Commerce Volunteer Fair

Fall FunFest

Downtown Chestertown - High Street & Memorial Plaza - Downtown Chestertown - High Street & Memorial Plaza

September 24, 2-5pm, the Kent County Chamber of Commerce will stage a free, carnival-style midway on High Street, featuring prize games of skill and chance, a bounce house, a sound stage with calliope music, beer, wine and popcorn. Brian Moore of WCTR will be the MC and will be drawing raffle tickets for fun adventures.… Continue Reading Fall FunFest

Rhythm & Brews

Foot of High Street - High Street & Water Street

Join the Kent County Chamber of Commerce as we host the our 4th annual beer fest, Rhythm & Brews, in Historic Downtown Chestertown, MD on Saturday, April 15th (rain date Sunday, April 16th). Enjoy craft beer from DelMarVa and beyond | Live Music | Food Trucks | and More Featured Breweries Include: Blue Earl Brewing… Continue Reading Rhythm & Brews

CANCELED – Fall FunFest

Downtown Chestertown - High Street & Memorial Plaza

CANCELED Fall FunFest will feature a free, festive, carnival-style midway with games and prizes hosted by local businesses and organizations. Beer, wine, cocktails, popcorn and fun for all ages.

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