Underground Railroad Comes to Oakwood School

POUGHKEEPSIE – From Sandy Spring, Maryland to Oakwood Friends School in Poughkeepsie to Ontario, Canada, and multiple East Coast cities in between, #FreedomWalk2026 is a modern-day retracing of the Underground Railroad to Canada, on the 250th anniversary of America’s independence. The walk will commemorate the brave self-liberators, the abolitionists, and their secret networks. The walk team, led by historian Anthony (Tony) Michael Cohen—who first walked the route in 1996—will trek 750 miles by foot, boat and rail using modes of transport of the original freedom seekers. Oakwood Friends School was honored to host the inspiring group of intrepid travelers as they made their way through the Hudson Valley recently.

Head of School Chad Cianfrani reflected on #FreedomWalk2026, sharing, “This moment connects deeply to Oakwood’s history. Tracing its roots to Nine Partners Meeting, Oakwood is grounded in a Quaker tradition shaped by equality, community, justice, and the inherent dignity of every person. Figures such as former teacher Lucretia Mott and many other Friends helped lead abolitionist efforts, and this journey echoes that legacy in a powerful and present-day way. It is a meaningful and mission-aligned opportunity for our community, an invitation to connect past and present, and to reflect together on the ongoing work of justice, equity, and freedom.”

The walk launched from Sandy Spring, MD on May 4, 2026, on the 30th anniversary of the original walk, and will conclude in Ontario, Canada on July 4, 2026. Each week the walkers will establish a base of operation in a different city along the way, where they will co-host events with local communities around the themes of history and community empowerment. Events will include teach-ins, service projects, lectures, installations and tours as well as opportunities for the public to walk with our team. Together with Poughkeepsie Friends Meeting, Oakwood welcomed members of the public to their campus for a bonfire gathering with moments of silence, song and a sharing from Tony about his journey – what it was like in the past, what it is like today, and what it stands for now, in this particular day and time.

Tony expressed his gratitude for the group’s time spent in Poughkeepsie, “Oakwood Friends School provided the #FreedomWalk2026 team with more than just a place to rest our heads. The school embraced us as family, offering shelter, sustenance and a restorative environment, in the long tradition of aiding those in need which defined the Underground Railroad.”

Other components of the #FreedomWalk2026 visit to Poughkeepsie included two local walks, one focusing on The Role of Local Churches in the Anti-Slavery Movement highlighting the places of worship and people that were influential in the anti-slavery movement, including Smith Metropolitan AME Zion Church, First Congregational Church, and Second Baptist Church. The second walk, River Trail to Freedom and Walkway Over the Hudson, led participants from the Celebrating the African Spirit memorial in Waryas Park, through Upper Landing Park, across the Walkway Over the Hudson, and ended at the Sojourner Truth statue to highlight the history of the anti-slavery movement and influential leaders in our area. #FreedomWalk2026’s time in Poughkeepsie concluded with a community celebration at the Family Partnership Center Family with a welcome from Mayor Yvonne Flowers, a blessing, music, reflections, and remarks from Tony Cohen.