History on the Waterfront
A free, audio-guided tour of Chestertown’s historic waterfront.
Fridays 12-4 p.m. and Saturdays 11-4 p.m.
About the Tour
The History on the Waterfront multimedia program offers a walk back in time into an era when the streets of this port town bustled with revolutionaries and convicts, slave traders, British soldiers, and heroes of the Underground Railroad. Connecting Chestertown’s rich history to the stories of the colonial Chesapeake, and by extension, the larger stories of America, this free thirty-minute audio-guided tour recreates the sights and sounds of an 18th-century working waterfront.
History On the Waterfront was created by Washington College’s C.V. Starr Center for the Study of the American Experience, and researched, written, and performed by Washington College students, faculty, and staff, and members of the wider Chestertown community. Beginning at the c. 1746 riverfront Custom House and extending along Chestertown’s historic waterfront, the tour includes narrative, music, reenactments, and firsthand accounts of life in the colonial port.
Exploring the inside of the Custom House, tour participants delve into the lives of past residents, including Thomas Ringgold IV, who was both a leader in the fight for colonial rights and, at the same time, a large-scale slave trader. Other actual historical figures in the tour include Isaac Mason, a young Chestertown slave who escaped through the Underground Railroad. Read Isaac Mason’s story here.
Participants will have an opportunity to see a reproduction of one of Washington College’s most treasured artifacts, a 200-year-old painting of Chestertown, done by an anonymous artist a few years after the Revolution. One of the very few surviving depictions of an 18th-century Chesapeake landscape, and perhaps the richest in detail, the painting provides a unique visual entry point into the world the tour recreates. Participants will also hear modern arrangements of 18th-century songs authored here in Kent County by an enslaved man named Cuffee.
History on the Waterfront was orchestrated by the Starr Center’s Jill Ogline Titus, and narrated by the Center’s director, Adam Goodheart. Program manager, Michael Buckley, who also produces the weekly radio series “Voices of the Chesapeake Bay” oversaw technical production.
Click here for a printable version of the tour brochure.
Reservations to take the tour may be made by calling 410-810-7161,
or emailing firstname.lastname@example.org.
Tours begin at the Custom House, 101 S. Water St. in Chestertown.
All tours are free of charge.
Tours run Fridays 12-4 p.m. and Saturdays between 11-4 p.m.
This project was made possible by a grant from the PNC Foundation Legacy Project with support from the Maryland Humanities Council. The Maryland Humanities Council is an affiliate of the National Endowment for the Humanities. Any views, findings, conclusions, or recommendations expressed in this program do not necessarily represent those of the PNC Foundation, the Maryland Humanities Council, or the National Endowment for the Humanities.
Other major funding for the tour has also been provided by the Helen Clay Frick Foundation and the Stories of the Chesapeake Heritage Area.
Other Places to Visit
For additional opportunities to explore the maritime history of the Chesapeake region, check out Chestertown’s own tall ship, Schooner Sultana, drop by the Geddes-Piper House (home of the Historical Society of Kent County), or visit the Chesapeake Bay Maritime Museum in nearby St. Michaels, Md. For a self-guided architectural walking tour of Chestertown, click here.