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October 14, 2026

ARCHIVE Chestertown Spy

Nonpartisan and Education-based News for Chestertown

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5 News Notes

Kent County Celebrates it’s 5th Annual National Night Out 

August 10, 2025 by The Spy Desk

In its 5th consecutive year, Kent County youth, families, non-profits, and law enforcement came together to build camaraderie and promote a safe and caring community. 

Event partners were Minary’s Dream Alliance, Kent County Local Management Board, Kent County Health Department Office of Prevention, Parks and Recreation, and Public Safety partners from Parole and Probation, Chestertown Police Department and Kent County Sheriff’s Department. Many other agencies and organizations were in attendance and shared information about their services and handed out fun takeaways for kids.  

The evening began with an intense game of kickball between public safety vs. youth and youth development leaders. Bryan DiGregory, Kent County’s State’s Attorney, served as the keynote speaker and umpire. Naturally, the youth team was victorious with a score of 5 to 3. Afterwards, there was a pick-up kickball game for children and families eager to play.  

The organizers also presented the 1st annual Vanessa Maddox Community Service Award. Over a dozen members of Ms. Maddox’s family traveled from near and far to share the moment and establish her legacy of service and compassion for Kent County’s children. 

The award was given to Washington College’s Hip Hop Time Capsule Program, which concluded its 5th annual summer internship session on July 18th. As part of that program, 36 paid high school interns, many of whom were in attendance that evening, worked with college mentors to create mural art, silk screen pieces, metal and wood working projects, and music recordings that honor the tradition of labor and innovation in the Uptown Chestertown area. 

The evening concluded with a pool party at the Community Center, free and open to all. 

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Filed Under: 5 News Notes

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