The Overnight is an orientation experience wherein all freshmen learn, and buy-in to, the St. Benedict’s ethos. This experience lasts a full week and includes students attending school, completing orientation activities, and sleeping each night on the gym floor.

To close-out their freshmen year experience, students have to complete a 55-mile hike on the Appalachian Trail, all the while traveling in groups of approximately eight students. The purpose of the Trail is to foster leadership and a sense of collaboration among students who are expected to stay together throughout the entirety of the trail.

"Stay Together"

"Stay Together," a term coined by the late leader and founder of St. Benedict's Backpacking Project, Fr. Mark Payne, O.S.B. '69, helps Gray Bee freshmen while they navigate "The Trail." The 55-mile hike over the Appalachian Trail begins at High Point State Park and concludes at the Delaware Water Gap in Northwest New Jersey. The Backpacking Project was chronicled by filmmaker, Chris Gallaway, during May of 2018 for the Appalachian Trial Conservancy.