25. Choptank Landing

Site of Harriet Tubman’s Most Daring Rescues

Harriet Tubman’s parents were active in the Underground Railroad in this area, and she most likely made her first escape from near here. Dr. Anthony C. Thompson employed Tubman’s father, Ben Ross on his 2,200 acres of heavily forested land in Poplar Neck during the late 1840s and 1850s. He also employed large numbers of free and enslaved black laborers in his timbering operations and sawmill.

On Christmas Day 1854, Tubman led her three brothers to freedom from Poplar Neck. Robert, Ben and Henry, and several others hid in a corncrib until dark, when they could begin their journey north. At nightfall, Tubman safely led them towards freedom, traveling through Delaware, Pennsylvania and across upstate New York to St. Catharines, Ontario, Canada.

Josiah Bailey, a skilled shipwright, escaped slavery in November 1856 by rowing a boat at night six miles from Jamaica Point in Talbot County up the Choptank River. He passed by here on his way to Poplar Neck. Then he met with Ben Ross, Tubman’s father, to plan his escape the next time Tubman was ready to go.

In March 1857, Ben Ross was suspected of aiding the escape of eight slaves, called the Dover Eight. Harriet Tubman rushed to the Eastern Shore to rescue her parents at great risk to herself before her father could be arrested. Cobbling together a makeshift, one-axle wagon, she rigged up a horse with a straw collar and drove her parents toward Delaware. They eventually made their way to St. Catharines, Ontario, Canada with the help of numerous Underground Railroad agents along the way.