The Spirit Lives on! — Chestertown High School Reunion


The last of the Dragons! CHS Class of 1971 — Photo by Jane Jewell

Ah, summer!  School is out, but school reunions are on!  For Chestertown, however, the high school is long gone. It merged with three other local high schools in 1972 to form Kent County High School located in Worton.  But Chestertown High School lives on in the hearts of its graduates and also at the annual  CHS All-Alumni Reunion held this past Sunday, Aug. 11, 1:00 – 5:00 pm at the Kent County Fairgrounds near Tolchester.  Several hundred people gathered there to greet old friends and reminisce about old times.  In their day, this lovely picnic site was a Nike Missile Base, with restricted military access only.  But it has officially been the Kent County Agriculture Center, home of the Kent County Fair for many decades now.  And the home of the Chestertown High School Alumni Association’s reunion picnic for the past 22 years.

While the majority of attendees still live in or near Kent County, a fair number came from farther away. This was especially true of the classes of ’59 and ’69, which threw their own special anniversary celebrations during the weekend. One ’59 graduate came all the way from Gainesville, Florida, and there were others at the picnic from southern Virginia and undoubtedly even more distant parts. And every year, a fair number of grads come across the Bay Bridge or down from Pennsylvania to visit family before or after the picnic.

Attendees are treated to a potluck spread that runs the gamut from hot dogs and fried chicken to baked beans, mac and cheese, fresh local garden veggies, and an impressive choice of desserts. And all for only $5 per person — whether alumni or guest!

The oldest graduate present was Ralph Thornton from the CHS class of 1936.  He graduated 83 years ago.

Ralph Thornton CHS Class of 1936 with a friend — Photo by Jane Jewell

The youngest alumni present were from the class of 1971 – the last class to graduate from Chestertown High School.  They proudly carried a sign proclaiming themselves “The Last of the Dragons.”  In order to avoid favoritism, it was decided that the new county high school would not use the mascot name of any of the smaller schools that combined to form the new school.  Thus the Chestertown Dragons were no more and the Kent County Trojans were born.

The all-alumni reunion is open to all who worked at, attended, or graduated from CHS, and their guests.  Annie Coleman, CHS class of 1967, is the president of the Chestertown High School Alumni Association, and one of the main founders of the annual picnic.  Held each year in August, the reunion is impressively organized.  Volunteers arrive early Saturday morning to set up the tables and chairs.  On Sunday, the class registrars set up shop with hundreds of pre-printed name badges and blank ones available for those who make last-minute decisions to come.  If you haven’t paid your $5 yet, they’ll take it then.   This also makes you an official member of the CHS Alumni Organization, which sends out two newsletters per year and awards a scholarship each spring to a current Kent County student.  You can also buy a chance for the 50/50 raffle with proceeds going toward the scholarship. Send dues or scholarship donations to Chestertown High School Alumni Association at PO Box 765, Chestertown, MD 21620.

Can you help us identify people?  Are you in a photo?  Or do you recognize a friend or relative?

Photos by Jane Jewell.

The last of the Dragons! CHS Class of 1971 

Fourteen members of the class of 1969 were there to celebrate their 50th reunion.  Seems like yesterday!

CHS Class of 1969 at their 50th Reunion

CHS Class of 1943 & ’44 

One of several classic cars brought to the CHS Reunion CHS — 

Antique car at CHS All-Alumni Reunion Aug 11, 2019 — Photo 










Kent County Fairgrounds Pavillion – site of Chestertown High School All-Alumni Reunion CHS

CHS Class of 1946

CHS Class of 1948 

CHS Class of 1949 

CHS Class of 1952


















CHS Class of 1953 

CHS Class of 1954










CHS Class of 1955 

CHS Class of 1956










CHS Class of 1957 — Photo by Jane Jewell

CHS Class of 1958 — Photo by Jane Jewell










CHS Class of 1959

CHS Class of 1961 — Photo by Jane Jewell










CHS Class of 1962 — Photo by Jane Jewell

CHS Class of 1963 — Photo by Jane Jewell












CHS Class of 1964 — Photo by Jane Jewell

CHS Class of 1965 — Photo by Jane Jewell










CHS Class of 1966 — Photo by Jane Jewell

CHS Class of 1967 — Photo by Jane Jewell











CHS Class of 1970 

CHS Class of 1968 
















Letters to Editor

  1. Robert Randall says

    I see no mention in the story of the reunion of the history of a former all-white segregated school which was only integrated many years after Brown v. Board of Education. Like 24 years later. I wonder if that’s got anything to do with why they were all smiling.

    This seems to me like a seriously troubling omission.

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