Celebrating strength, resiliency of Kent’s historic Black communities

CHESTERTOWN — A sampling of Kent County’s historic Black communities — 10 of the more than 20 that have been documented — was toasted, literally and figuratively, during the 12th annual Legacy Day celebration.

Glasses were raised in tribute to Big Woods, Butlertown, Coleman [also known as Colemans or Coleman’s Corner], Edesville, Georgetown, Golts, Olivet Hill, Pomona, Sandfield and Worton Point on Friday night, Aug. 15 during the opening reception at the Garfield Center for the Arts in downtown Chestertown. This was after representatives of these venerable communities were called up to be recognized.

Legacy Day is produced annually by Sumner Hall in cooperation with the Historical Society of Kent County.

For Vanessa Ringgold, president of the Sumner Hall board of directors, this year’s theme of historic Black communities was deeply personal.

“They represent strength, resiliency and love … Our ancestors created spaces for families to thrive,” said Ringgold, who grew up on South Queen Street, Chestertown, in the area known as “Boardwalk.”

To the representatives from each of the 10 honored communities, she said, “You are the heartbeat of Legacy Day.”

Bill Leary, who co-curated this year’s Legacy Day exhibit with Ringgold, noted that the sizable number of historic Black communities in Kent — “there are a lot of them,” he said — is remarkable for the smallest county in the state.

Equally remarkable is the number of success stories that have come out of these communities, “despite poverty and racism that threatened their very survival,” Leary said.

The personal triumphs have run the gamut of elected government leaders such as County Commissioners Clarence Hawkins and William Pickrum and Clerk of the Circuit Court Sherise Kennard; to social leaders such as Catherine Boyer Sterling, Mary Grinnell, Delia Caulk and Ruth Briscoe; to entrepreneurs such as funeral director Kenneth Walley, blacksmith Moses Caulk, masons Clyde and Grover Freeman and bus company owner Curtis Dorsey; to educators such as Eloise Johnson, Charlotte Potts and Irving Hamilton; to cultural leaders such as Karen Somerville and Marlon Saunders; and to artists such as John Mason.

Most of these historic Black neighborhoods were small, 100 to 275 residents, and many of them no longer exist.

While they all had their own culture, history and identity, they all also were about community — establishing it, maintaining it and gaining strength from it.

Friday night’s opening reception at the Garfield Center, which was cabaret-style with live music and refreshments, was a standing room-only event with the overflow crowd seated in the balcony.

In his welcome, Nivek Johnson, the Legacy Day Committee chairman, said, “Outside of the county’s five municipalities are some of Kent’s treasures, its Black communities.”

In these times of uncertainty and turmoil, Johnson added, “There’s something powerful and healing about remembering where we come from.”

Legacy Day has expanded over the years into a multi-day festival that celebrates the rich cultural heritage of Kent County’s African American community.

This year’s event ran from Friday through Sunday, Aug. 15-17 at various venues in downtown Chestertown.

An exhibit — photographs, narrative text and maps — featuring these 10 historic Black communities opened Aug. 1 at the Historical Society of Kent County’s Bordley History Center at 301 High St. and will continue until the end of September.

Legacy Day 2025 kicked off with a pre-opening public art performance titled “Making Memory Move” on the Custom House lawn, combining dance, music and “critical interpretation” to honor the lives of African American women whose names have been lost to history.

The reception followed at the Garfield Center.

Activities on Saturday included a “Blacks on the Chesapeake” digital display at the Sultana Holt Center; an African American walking tour of downtown Chestertown led by staff from Chesapeake Heartland: An African American Humanities Project; and public sails on the Chester River aboard a replica of the 1768 schooner Sultana.

In the afternoon, all Legacy Day activities moved to the Fountain Park area where there were food vendors, craft vendors and information booths.

A parade of historic and classic vehicles in honor of the late Mary Fisher followed a route along High Street, stepping off in the “uptown” area and concluding in the 200 block. The Mary Fisher Legacy on Wheels Parade featured more than 40 cars and trucks, in addition to about a dozen Polaris Slingshot three-wheelers.

For many years, Fisher was the key organizer for the Legacy Day parades. An educator, coach and administrator in Kent County’s pubic schools, she passed away in September of 2024.

Following the parade, the focus shifted to the main stage at the intersection of Park Row and Cross Street, where there were performances of songs, dance ministry, and recitations and readings.

Comfort Zone, known for playing classic R&B hits, was the featured musical entertainment.

The Legacy Day weekend wrapped up Sunday with a champagne brunch, sponsored by and hosted at Emmanuel Episcopal Church. More than 80 people attended.

This year’s brunch theme was “Hidden Figures,” a celebration of influential Black trailblazers in Kent County.

The script was written by Cheryl Hoopes. Airlee Johnson and Leslie Raimond were the producers.

The skit, with an intermission, featured reenactors in roles that included Henry Highland Garnet, the namesake of H.H. Garnet Elementary School in Chestertown; Emma Grason Miller, Kent County’s first Black supervisor of colored schools; Harriet Shepherd, who escaped from slavery along with 10 others by taking her master’s carriages and four horses; Isaac Mason, whose autobiography details his 1846 escape from enslavement in Chestertown, how he found freedom across the Pennsylvania border and his rise to become a distinguished American leader; abolitionist, pastor and orator Samuel Ringgold Ward; and Richard Allen, founder of the African Methodist Episcopal (AME) Church.

“The outpouring of support from the community for this year’s Legacy Day was tremendous,” Vanessa Ringgold wrote in an email to The Evening Enterprise.

“From the very first program — ‘Making Memory Move’ with the Starr Center at the Custom House, to the Historic Black Communities Cabaret at the Garfield, to the Blacks on the Chesapeake digital display at Sultana, to the Mary Fisher Legacy on Wheels Parade down High Street, to the Gospel Showcase with music and vendors in the park, and finally topping it all off with the Hidden Figures Champagne Brunch at Emmanuel Episcopal Church — this year’s Legacy Weekend was one of the most successful in the twelve-year history of the event,” Ringgold wrote in the email.

She said the focus on historic Black communities in Kent County “resonated deeply with many, making this year’s Legacy Day event more inclusive than ever — and the community responded with an increase in sponsorship, in attendance at events and in the positive feedback.”

“Exceptional” was Legacy Day Committee Chairman Nivek Johnson’s one-word descriptor in a text message to The Evening Enterprise.

He said the program “really captured the essence of the rich and vast history of Black Kent Countians.”

“We hadn’t utilized Fountain Park since 2019, so it was a bit of a change logistically for the whole team, but it made for a more intimate festival and provided much shade,” Johnson said in the text message.