The former Preston Plantation found at the end of Rodgers Road near Bedford is considered to be one of the more significant Underground Railroad sites in Trimble County. Underground Railroad historian Diane Coon said that it was easier to hide fugitive slaves at a site like Preston, which had around 50 slaves, than at smaller farms that might have only had two or three slaves. (Staff photo by Ken Ritchie/kritchie@madisoncourier.com)
The former Preston Plantation found at the end of Rodgers Road near Bedford is considered to be one of the more significant Underground Railroad sites in Trimble County. Underground Railroad historian Diane Coon said that it was easier to hide fugitive slaves at a site like Preston, which had around 50 slaves, than at smaller farms that might have only had two or three slaves. (Staff photo by Ken Ritchie/kritchie@madisoncourier.com)
The Ohio River served as a boundary between northern free states and southern slave states, but the waterway didn't stop hundreds of slaves from crossing it on the journey to freedom.

Just across the river from a location with some of the most documented sites connected to the Underground Railroad, Trimble County, Ky., has several areas of a historical significance not identified by historical markers.

In fact, Trimble County had one of the largest and well-known escape routes for slaves seeking freedom during the 1800s, Underground Railroad historian Diane Perrine Coon of Louisville said during a presentation Thursday.

"We can prove there were three crossing points in this area," she said, noting people in Madison were most likely the reason for such a high concentration of activity in the area. "You had this group of people right across the river that had a natural instinct to help."

In her 15 years of research, Coon found a crossing near the border of Trimble and Carroll counties known as Eagle Hollow that served as one of the most active Underground Railroad crossing points in the area.

Richard Dailey, an enslaved person from a nearby farm, would ferry other slaves to the middle of the Ohio River where Underground Railroad conductors - people who helped fugitive slaves escape to freedom - from Indiana would meet to take people farther on their journey north. Other farmers in the Eagle Hollow area also helped slaves to the freed northern states by providing protection and hiding spaces, Coon noted in her research.

The crossing at Milton also served as a major route from 1818 to 1860 for slaves. An estimated 500 slaves might have crossed in steamboats or river rafts, while others crossed near the Saluda ravine near Hanover. Others crossed from the Cooper's Bottom area to the Clifty Falls area.

"The river was real easy (to cross) in those days," Coon said, noting people could often walk across the river in winter or during severe droughts. "For most of those fugitives, they thought as soon as they crossed that river they were safe."

But freedom wasn't that simple for fugitive slaves, she said.

Trimble County's participation with the Underground Railroad caused quite a stir in the county. While a few people joined in with abolitionists from Indiana that crossed the Ohio River to recruit Trimble County residents to their mission, others served on search groups and traveled across the river to look for fugitive slaves.

"So you had this tension all the way through the Civil War," Coon said.

Records show nearly 50 slaves from Trimble County farms escaped during the early 1800s. Some slaves from Kentucky and other southern states escaped through Trimble County prior to the Underground Railroad organizing in the area.

"There are a lot of slaves that got to the river without help," Coon said, yet hundreds of other slaves made it to freedom in the north with the help of Underground Railroad conductors.

Delia Webster served as one of the major connections for the Underground Railroad in Trimble County. A Vermont native, Webster and Calvin Fairbanks helped three slaves escape across the Ohio River in 1844, just a year after her arrival in Kentucky. She was sentenced to two years in the penitentiary for her actions, but was later pardoned by former Kentucky Gov. William Owsley.

Webster left the state after her two years in prison, but she returned to Kentucky in 1854 and purchased a farm near Milton overlooking the Ohio River and Madison. Known as the "petticoat abolitionist," her home became well-known as being a stop on the Underground Railroad as documented by a neighbor years later in a letter to The Madison Courier.

Susan Moffett Inglis wrote a 1938 letter noting that while her father did not participate in Underground Railroad activity in Trimble County, others in the area did.

"My father was a slave holder - so that proves he was not connected with the traffic spoken of nor was it carried on on his farm," the letter said. "The place was the farm farther north west owned by one Delia Webster..."

Coon's research showed Webster was jailed for helping fugitive slaves and other Underground Railroad activity in Trimble County.

A free African American known as the "superintendent" of Madison's Underground Railroad, Elijah Anderson, was also jailed and convicted in Bedford for his work helping fugitive slaves escape across the river, Coon's research showed. He was murdered on the day he was to be released from jail.

Other homes and caves near the Ohio River served as safe places for people traveling on the Underground Railroad as well.

"They'd be looking for hiding places near the river," Coon said.

Caves were utilized as temporary safe spaces, or depots, for the Underground Railroad.

"We know that the Underground Railroad used Wilson Cave" and other caves in the area, Coons said. "They would put the fugitive in these caves just long enough to get another abolitionist (usually from Indiana)."

Several of the locations with historical significance to the Underground Railroad - like the caves - still remain undiscovered and unmarked throughout Trimble County on private properties not accessible to the public.

"You have lots and lots of historical significance here," Coon said.