CHESTERTOWN — In the decades immediately before and after the emancipation of Maryland’s enslaved population, from about 1850 to 1870, African Americans established 10 communities throughout rural Kent County that Legacy Day 2025 will honor.
So begins the introduction penned by Bill Leary and Vanessa Ringgold to this year’s Legacy Day booklet, which showcases Big Woods, Butlertown, Coleman, also known as Colemans or Coleman’s Corner, Edesville, Georgetown, Golts, Olivet Hill, Pomona, Sandfield and Worton Point.
(In the second half of the 19th century, at least 10 more small Black communities were founded, including Broad Neck, Chesterville Forest, Cork Town, Davis Hill, Johnsontown, Melitota, Mt.Pleasant, Sandy Bottom, Sassafras, and Still Pond’s Dutch Town.)
At their peak, in the early 20th century, the 10 communities discussed in this year’s booklet ranged in size from about 100 to 275 residents, according to the scholarly research presented by Leary and Ringgold.
“They were settled to strengthen the bonds of community and to sustain a feeling of enhanced safety and mutual help when needed,” the Legacy Day booklet states.
These communities shared many characteristics, including:
• They were located adjacent to the large farms that provided the almost exclusive source of employment for Black people, even after emancipation and up to World War II.
• Extensive family networks fortified community bonds.
• Each community was built around the essential community institution, a Methodist church.
Most also had a small school, usually attached to the church.
• Most had a few commercial establishments, such as a convenience store, barbershop and a beer garden.
The is the 12th edition of Legacy Day, which 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, under the ongoing sponsorship of Sumner Hall, runs 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 will kick off on Friday with two events: a pre-opening public art performance at 6 p.m. on the Custom House lawn (101 High St.) followed by a reception at 7 p.m at the Garfield Center for the Arts (210 High St.).
The public art performance, titled “Making Memory Move,” is sponsored by Washington College’s Starr Center for the Study of the American Experience. According to a news release, the performance will combine dance, music and “critical interpretation” to honor the lives of African-American women whose names have been lost to history.
The Legacy Day opening reception will recognize the communities and community members who are being honored this year. It will be a cabaret with live music and refreshments.
Activities will resume on Saturday at 9:30 a.m. with a “Blacks on the Chesapeake” digital display at the Sultana Holt Center (200 S. Cross St.). This is an immersive and moving presentation that lights up the floor — literally and figuratively — as it guides audiences through the rich and often untold stories of African American life and legacy on the Eastern Shore.
An African American Walking Tour of downtown Chestertown led by staff from the Chesapeake Heartland: An African American Humanities Project will immediately follow “Blacks on the Chesapeake” display. The tour will begin at Cross and Cannon streets, and will explore the streets and structures that once formed the heart of Chestertown’s Black community.
The Sultana Education Foundation will offer two opportunities, at 10 a.m. and 1 p.m., for community members to join the crew of the 1768 schooner Sultana for a two-hour sail on the Chester River. Passengers are encouraged to help raise sail, steer using Sultana’s 7-foot tiller and explore the authentically reproduced crew’s quarters below decks.
At 1:30 p.m., Legacy Day will move to High Street and open with a parade of historic and classic vehicles in honor of the late Mary Fisher in what is being called the Mary Fisher Legacy on Wheels Parade. For many years, Fisher was the key organizer for the Legacy Day parades. An educator, coach and administrator in Kent County’s pubic schools, Fisher passed away in September of 2024.
Following the parade, the Gospel Showcase will begin on the main stage in the 300-block of High Street at 2 p.m. There will be performances of songs, dance ministry, recitations and readings by local and regional artists to celebrate the central role of gospel in Black history and culture.
The official Legacy Day dance party will begin at 4 p.m. with DJ Turbulance. Community members will be asking “Where them fans at” with “Boots on the Ground” and other line dancing hits.
“This year we are making a strong effort to involve youth in the Legacy Day events and are introducing a youth dance contest. By offering cash prizes, we hope to highlight their talents and reward them for stepping up as active participants,” said Ringgold, president of Sumner Hall’s board of directors.
Young dancers can sign up in advance on the Sumner Hall website, https://sumnerhall.org/, or join in at the time of the event.
Legacy Day will continue on Saturday with a celebrated evening of dancing in the street to the tunes of Comfort Zone, known for playing the classic R&B hits, beginning at 5 p.m.
Food vendors, craft vendors and information stations will be on site throughout the day to provide nourishment and other “goodies.”
The Legacy Day weekend will conclude Sunday at 1 p.m. with a champagne brunch, sponsored by and hosted at Emmanuel Episcopal Church (101 N. Cross St.).
This year’s brunch theme is “Hidden Figures,” a celebration of influential Black trailblazers in the history of Kent County. Reenactors will take the roles of such luminaries as Henry Highland Garnet, the namesake of H.H. Garnet Elementary School in Chestertown, and Richard Allen, founder of the African Methodist Episcopal (AME) Church. Several other “hidden figures” will be portrayed as well.
All Legacy Day events are free and open to the public.
Due to space limitations for some of the venues, reservations are recommended.
For reservations and more information, visit https://sumnerhall.org/.
For more information, email info@sumnerhall.org.
