Many long-time residents of Sag Harbor would be surprised to learn that evidence suggests locations in the historical Eastville community were stops on the Underground Railroad.
Of course, traveling from the South to the East End of Long Island to further north is somewhat of a circuitous route, which made Eastville an unpopular destination on the route. However, the fact that any amount of slaves stayed at buildings many of us walk by every day is remarkable. The possibility localizes a crucial part of American history that is often difficult for people today to truly grasp.
The St. David African Methodist Episcopal (AME) Zion Church, built in 1839 by African Americans and Native Americans, is the oldest church in Sag Harbor still on its original site. Lewis Cuffee, Charles Plato and William Prime founded the church so that African American and Native American families would not have to deal with the racism and segregation they experience at another church in Sag Harbor. The AME Zion Church quickly became the linchpin of the community.
One of the church’s first pastors, J.P. Thompson, was a known abolitionist and friend of Frederick Douglas. Thompson is also buried in the AME Zion Cemetery, which is shown during tours at the historical society. Although the evidence is scant, some historians believe that Thompson and Cuffrey worked with the local Quakers to create Underground Railroad stops in Eastville. The Quaker community in Sag Harbor was very involved in anti-slavery efforts during the mid-1800s. The church contains two trap doors, one by the pulpit and the other under the library at the back of the church, that might have connected to the Underground Railroad network.
Historians at the Eastville Community Historical Society are also interested in whether Native Americans on Long Island assisted slaves travelling on the Underground Railroad. Native Americans could have shared their hunting and fishing routes with slaves unfamiliar to the area. The Underground Railroad on Long Island passed through land inhabited by Shinnecock Native Americans, which slaves had to traverse in order to get to Upstate New York.
Historical homes on Liberty Street and Hempstead Avenue, which is named after the slave-owning Hempstead family, in Sag Harbor were also possible stops on the Underground Railroad. Several of these homes have trap door cellars. Again, so far there is no definitive evidence that these homes were designated “safe homes” along the Underground Railroad. Hopefully more research will uncover the truth.
Due to COVID-19, the Eastville Community Historical Society is not currently giving tours. However, their website has a self-guided tour, which can also be accessed through a phone app. Stops on the tour include the AME St. David AME Zion Church, the Ivy Cottage, a popular hotel and restaurant for African-Americans in the 20th Century, and homes of notable Algonquin and Montaukett Native Americans.
The homes on Liberty Street and Hempstead Avenue are also a part of the tour, including the residence of Colson Whitehead, the two-time Pulitzer Award for Fiction winning author. Whitehead has spent time in Eastville since his teenage years and wrote a book based on his experience called “Sag Harbor.” He was also recently profiled on 60 Minutes.
The history of Eastville is fascinating and much-maligned. One cannot walk down Eastville Avenue or Liberty Street the same after learning about its possible connection to the Underground Railroad. Visiting the Eastville Community Historical Society, or its website until it reopens, is a great resource for educating oneself on this profound part of our past.