On the morning of Friday, May 29, 2026, students from the Tappan Hill School gathered in the wooded area that is part of its campus. Joining them were Raymond Sanchez, Superintendent of the Public Schools of the Tarrytowns (TUFSD), members of the Board of Education, school administrators, and residents from Sleepy Hollow and Tarrytown. They were there for the official opening of the Tappan Hill Trail.
In the words of the TUFSD, the trail “gives students a dedicated outdoor space to explore nature, engage in hands-on learning, and build a real connection to the environment around them.” The school district also asserts that the winding path is “designed not just to connect nearby neighborhoods to campus, but to spark curiosity and a love of the outdoors in the students who walk it.”
“A new path is winding its way through Tappan Hill School—one designed not just to connect nearby neighborhoods to campus, but to spark curiosity and a love of the outdoors in the students who walk it.” —Public Schools of the Tarrytowns
The statement speaks to a key goal of the trail: to provide students, caretakers, and family members a safe and enjoyable walking route between Ichabod Lane and Rosehill Avenue and thus encourage more people to walk to and from the school. However, a barrier at the Rosehill end of the trail currently prevents this from happening.
Volunteers from various organizations first constructed the trail on May 31, 2025—almost exactly one year before the opening ceremony took place. This involved the removal of large amounts of trash, the elimination of invasive vegetation, and the marking and delimitation of the actual trail.
While minor work remained (and still does)—particularly, the building of a small set of stairs and a landing at the Rosehill end given the trail’s steepness there—the TUFSD and the Village of Tarrytown have failed in the 13 months since the trail was built to see through its completion.
In December 2025, for example, Tarrytown’s Board of Trustees passed a resolution asserting that the school district had to receive Village approval for construction of any connection between the school property and Rosehill Avenue. More than six months later, the school district has not yet submitted the necessary paperwork.
Meanwhile, the Village of Tarrytown has aided and abetted the stalling by suggesting that the trailhead is unsafe due to the lack of sidewalks on Rosehill and a crosswalk near the point of access. It has also failed to implement measures that would bring about a safer pedestrian route to and from there—to remedy the very problems it decries in other words.
Livable Tarrytowns has played a major role in bringing about the trail. Indeed, Elizabeth Tucker, on behalf of Livable Tarrytowns, was a recipient of a 2025 Community Grant from the Greater Irvington Land Trust (GILT) that paid for materials used to construct the trail and to purchase native trees that have been planted.
That the trail has now partially opened speaks to the support it enjoys among many nearby residents, families in both Sleepy Hollow and Tarrytown who have children at Tappan Hill, and individuals throughout the two villages. It also highlights the need to complete the trail before school opens in September so that students and those accompanying them, in addition to the broader public, will have full access to the wooded path.
Whether or not the trail is completed, people will continue to walk to and from the Tappan Hill School. The question is, will the school district (and the Village of Tarrytown) provide a safer, more enjoyable pedestrian route to and from the site than currently exists?
To ensure that it does, Livable Tarrytowns urges readers to contact the Board of Education (boe@tufsd.org), Superintendent Sanchez (rsanchez@tufsd.org), and Tarrytown’s mayor and members of the Board of Trustees (see below) to voice their support for the trail’s completion.
Mayor Karen Brown: kbrown@tarrytownny.gov
Trustee Kenny Herzog: kherzog@tarrytownny.gov
Trustee David T. Kim: dkim@tarrytownny.gov
Trustee Becky McGovern: bmcgovern@tarrytownny.gov
Trustee Thomas Mitchell: tmitchell@tarrytownny.gov
Trustee Effie Phillips-Staley: EPStaley@tarrytownny.gov
Trustee Paul Rinaldi: prinaldi@tarrytownny.gov
Livable Tarrytowns 