Legacy Day Honors African American Teachers


As school reunions go, the fourth annual Legacy Day in Chestertown breaks the mold.  This reunion will have a parade and block party in downtown Chestertown, and no one will care where you went to high school.  Everyone is welcome.

Legacy Day always attracts a large and diverse crowd and this year’s celebration should be the largest yet.  The parade will start down High Street at 5:00 on August 19, and from 6:00 to 10:00, the nine-member band “Soulfied Village” will make music while old friends and new, locals and come-heres, mix, mingle and dance in the street next to Fountain Park.

Every Kent County Historical Society Legacy Day highlights the county’s past.  In 2014, the first Legacy Day celebrated Chestertown’s Uptown Club, a stop on vaudeville’s Chitlin Circuit that featured stars as bright as Etta James, James Brown, BB King, Fats Domino, Little Richard, Otis Redding, Ray Charles and Patti Labelle.

The stars this year are the African American teachers who taught pride and excellence along with academics before county schools were integrated in 1967.  Now in their 70s and 80s, nearly 30 teachers, or, in the case of those who are no longer living, their relatives or friends, will ride in the parade in classic cars and, appropriately, on a school bus.

The Grand Marshall of the parade, waving from a 1937 Buick Roadmaster convertible, will be Garnet High social studies teacher Lauretta Freeman.

“The teachers were surprised when I called,” said Airlee Johnson, chair of the Legacy Day Committee.  Physical education teacher Gloristeen Powell Pinckett exclaimed, “Thank you for remembering us old gals!” and Mildred Upshur said, “Oh my gosh!  You all had the brightest minds.  I’ve always wanted to know what happened to you.”

For many, Legacy Day will be a reunion worth the drive from as far off as Georgia.  For others—too young to remember the pre-Brown v. Board of Education days or who attended all-white schools—it will be a chance to share stories and party.

Bill Leary, a white member of the Historical Society Board and a member of the Legacy Day Committee, says he attended segregated schools in Washington’s Virginia suburbs when he was a boy.

“I love Legacy Day because it is a genuinely interracial celebration of African American culture in Kent County,” Leary said.  “It is also great fun, as hundreds of people gather in downtown Chestertown to listen or dance to great music, eat good food and catch up with old friends.”

In addition to the block party and parade, Legacy Day will sponsor a Genealogy Workshop at 10:00 am on Saturday at Chestertown’s Public Library.  There will be a reception for the teachers on Friday.

Johnson says most teachers coming to Legacy Day taught at Garnet High, but some taught at elementary schools for African American children scattered throughout the county.  “Before I went to Garnet, I went to Worton Point,” Johnson said.  “It was a one-room school for grades one to four.  There was a table for each grade, a big stove and no indoor plumbing.”

A graduate of Garnet, Kent County Commission President William Pickrum will ride in the Legacy Day parade, but when he was a child he and his brothers walked 2½ miles to the three-room Coleman School from their home at YMCA Camp Tockwogh in Still Pond Neck.

Johnson says every African American school had the same goals.  “The expectation in our schools was that we would all excel,” she said.  “In a way, our schools were like exclusive private schools.  The teachers were preparing us to go out into the integrated world.”


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