CHESTERTOWN — The 13th edition of Legacy Day sponsored by historic Sumner Hall, which celebrates the rich cultural heritage of Kent County’s African American community, runs from Friday through Sunday, Aug. 14-16 at various venues in downtown Chestertown.
As America celebrates the 250th anniversary of its declaration of independence, Legacy Day 2026 celebrates the achievements of Kent County’s African American population since 1776 in their pursuit of freedom and justice.
Many of the historic places, people and events are highlighted in an exhibit and accompanying Legacy Day booklet.
As the booklet states, “It’s a history worth remembering.”
The Legacy Day exhibit, which opened last week at the Historical Society of Kent County’s Bordley History Center [301 High St.], features a virtual railroad-track timeline of historic events from 1776 to the present day. The exhibit will continue on display throughout August.
The “Celebration Weekend” will launch with an honoree reception on Friday at 7 p.m. at the Garfield Center for the Arts at 210 High St. The honorees are African American elected and appointed officials who have served to improve the lives of all in our community.
Following a brief program, guests will be entertained by jazz saxophonist Anthony “Turk” Cannon and band.
On Saturday morning, activities will resume at 9:30 a.m. with a “Blacks on the Chesapeake” digital display at Sultana’s Holt Education Center at 200 S. Cross St. It’s 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 Chesapeake Heartland: An African American Humanities Project will immediately follow the “Blacks on the Chesapeake” display. The tour will begin at 10:30 a.m. at Cross and Cannon streets, and will explore the streets and structures that once formed the heart of Chestertown’s Black community.
Sultana Education Foundation will offer a complimentary sail at 1 p.m. for community members to join the crew of the replica 1768 schooner Sultana for a two-hour sail on the Chester River. Passengers will be encouraged to help raise sail, steer using Sultana’s 7-foot tiller and explore the authentically reproduced crew’s quarters below deck.
At 4 p.m., Legacy Day will move to High Street and open with the Mary Fisher Legacy on Wheels parade with a lineup of vehicles.
Following the parade, DJ Black Frost will heat things up with popular R&B tunes until the headlining group, Eastern Shore-based Soulfied Village, takes the stage.
DSW Soul Line Dance exhibitions also will be featured during the evening.
Food vendors, craft vendors and information stations will be on site throughout the day.
Check the Sumner Hall website, https://sumnerhall.org/, for any additions or changes to the event schedule.
Legacy Day weekend will conclude on Sunday, Aug. 16 at 1 p.m. with a champagne reception and author talk featuring Jason Green and his memoir “Too Precious to Lose.”
Green served as special assistant and associate White House counsel to President Barack Obama, advising on domestic and economic policy.
His book blends personal and community history with broader reflections on belonging, memory and civic responsibility.
This rare author event will be held at Emmanuel Episcopal Church, located at 101 N. Cross St., and supported by The Bookplate, which will have books for sale before and during the event.
All Legacy Day events are free and open to the public, though registration is strongly encouraged due to space limitations. For reservations and more information, visit the Sumner Hall website at https://sumnerhall.org/.
For more information, email info@sumnerhall.org.
