Harriet Tubman’s Legacy Reaches Hudson Valley Through Proposed Byway

Last month the Red Hook Town Board passed a resolution in support of the Harriet Tubman Underground Railroad New York Byway, a proposed 550 mile long corridor that will begin in Manhattan and extend all the way to St. Catherine, Ontario. The byway hopes to highlight the perilous journey escaped slaves took to freedom. 

The Underground Railroad was not an actual railroad, but rather a pathway linked by places where escaped slaves could find temporary refuge on the way to Canada. Dozens of sites with historical ties to the Underground Railroad across New York will be connected by the proposed byway, including the Harriet Tubman National Historical Park in Auburn and Fleming, the Gerrit Smith Estate in Peterboro, and the Nine Partners Meeting House in Millbrook. In Rhinebeck and Red Hook, two communities through which the byway will pass, the proposal has awakened new interest in exploring the role the towns may have played as stops on the Underground Railroad. 

“It’s important that we preserve history and the struggles of so many to obtain the freedoms that each and everyone of us is today entitled to,” Red Hook Town Supervisor Robert McKeon told The Daily Catch. “The byway represents an opportunity to do so.”  

In Dutchess County, the proposed byway will run north along Route 9 and Route 9G towards the Stephen & Harriet Myers historical site in Albany. It will pass through 22 counties in New York, and each of the more than 100 municipalities along the route must adopt a resolution of support for the project in order for it to be approved by the state legislature. The Town of Rhinebeck has yet to pass its resolution. 

Periodic signage will be placed along the byway to mark relevant sites on its path. These signs will be installed by the New York State Department of Transportation at no cost to the local municipalities. Sites receiving signage will be chosen by a byway management committee, which will be formed only if the state legislature approves the byway next year. However, the Underground Railroad was secretive by necessity, making it sometimes challenging to definitively identify sites.

“It’s very difficult to confirm that a building was on the Underground Railroad,” said Peter Bunten, executive director of the Mid-Hudson Antislavery History Project. “Everything was kept very quiet so you don’t often see documentation or newspaper articles about it from the time.”

During the late 18th and 19th century, escaped slaves passed through Dutchess County traveling north along the Albany Post Road, much of which today is Route 9, by ship on the Hudson River, or through a trail of Quaker meeting houses through eastern Dutchess County. While New York abolished slavery in 1827, attitudes towards abolitionism remained broadly hostile as the staunch antebellum politics of the Democratic Party dominated the region, according to historian and author Fergus Bordewich. Slave patrols, operating under the authority of the Fugitive Slave Act, hunted the escapees and earned $10 for each black person they sent south. Those caught sheltering the freedom seekers could receive a fine as high as $1000 (about $41,000 today) and six months in prison.   

Most Underground Railroad activity was centered around urban areas such as Poughkeepsie, where abolitionists and free black communities were more common as well as Quaker communities in areas like Pawling and Hudson. Nonetheless, there are likely many smaller sites where Underground Railroad activity happened across Dutchess County which have yet to be officially recognized, according to Bunten. 

One local site rumored to have ties to the Underground Railroad is the Beekman Arms in Rhinebeck. The longest continuously operating inn in the United States, the Beekman Arms opened its doors in 1766, making it old enough to qualify. The inn’s strategic location near the Albany Post Road and the Hudson River as well as a collapsed tunnel discovered in its basement have fueled speculation that it may have been a stop along the secretive trail.

“Could that area have served as a place to hide for somebody who was escaping to Canada? Yes,” said Rhinebeck Historian Mike Frazier. “Do we have any contemporary records to that effect? No.” 

The lack of documentation is not a surprise. “The danger is that anybody who might have been making such records made him or herself quite vulnerable to accusations of harboring slaves,” Frazier said.  

Nicole Coulon, general manager of the Beekman Arms, acknowledges that there is no concrete evidence to confirm the rumors that the collapsed tunnel in the cellar once sheltered people fleeing slavery. In the same way, Coulon notes there is no documentation proving George Washington stayed at the inn during the Revolutionary War—yet that story remains part of the hotel’s recognized history, even by the National Trust for Historic Preservation. The tunnel is estimated to have been constructed sometime in the 1820’s or 1830’s. It served a variety of clandestine purposes including storing illegal alcohol during Prohibition, according to Coulon. 

Bill Jeffway, executive director of the Dutchess County Historical Society, has theorized that Oak Street in Rhinebeck—just a short walk from the Beekman Arms—may have been a site of Underground Railroad activity. His hypothesis is based on the presence of several Black families who lived on Oak Street in the 50 years leading up to the Civil War, including some who had come from Maryland and one family of Black steamship captains.

“It’s a theory, but you can’t really find hard evidence,” Jeffway told The Daily Catch. “If there was Underground Railroad activity in Rhinebeck it was probably happening around that community because there was a big enough black community that you could kind of blend in.”   

Jeffway hopes that the byway inspires residents to learn more about the nuanced and complex stories of black history in their local communities. 

“The byway is a 21st century invention that only tells a sliver of the story,” Jeffway said. “But, if it can serve as an entry point for people to open the doors of curiosity and explore more complex stories from the time, then that’s a good thing.”  

The byway is part of a larger multi-state project to form a continuous route across Maryland, Delaware, Pennsylvania, New Jersey, and New York memorializing the life of Harriet Tubman and the history of the Underground Railroad. In the Empire State, the project is spearheaded by the Underground Railroad Consortium of New York State, a coalition of organizations dedicated to maintaining sites related to the Underground Railroad and organizing programs to educate the public on its history and impact.

Across the nation, similar byway projects have been boons to local communities along their path, according to the consortium. Established in 2013, Maryland’s Harriet Tubman Byway generates $23 million in additional sales per year and supports 363 jobs across the state.

“The successes of the Maryland byway have been well documented,” Bunten told The Daily Catch. “From increased interest in tourism, to financial benefit for the local economy, and creating opportunities for historical education; these are all wonderful things we would like to see more of in Dutchess County and beyond.” 

The Underground Railroad Consortium is aiming to collect resolutions of support from every municipality along the proposed byway by June, ahead of submitting a required management plan to the New York State Department of Transportation by September. Once they do, the state legislature can begin crafting legislation to officially establish the byway next January. 

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