Facing all 18 graduates, he shared his wisdom of life after secondary school.
"Follow your passion... persevere... and never quit," Wilson said.
The 18 graduates, all pursuing a wide range of careers and majors, listened while Wilson advised them how to overcome the obstacles that will come into their path. He told a humorous story of attempting to receive fund-raising money for the school from a donor, and of the unusual obstacles they met while attempting to do so. Their initial meeting place was closed for the winter, they were almost pulled over by a sheriff, and Wilson's cat attempting to eat their sandwiches all before they were even able to discuss fundraising, he said.
He also told stories of how the Long Trail School came to be, and how he approached the education board without having any students, faculty members, or even a building. He used his obstacles as an example of how never to give up when life throws you hardships.
After Wilson's commencement speech came the opportunity for each graduating senior to tell to the rest of the class, their relatives and friends in attendance, and even their teachers, just what Long Trail did for them.
"One of the Long Trail traditions, and I think one of the great ones... it's when each of the seniors have an opportunity to say some words, or share in their own way with the people attending this afternoon," said current Head of School Steven Dear.
Many tears were shed by graduates and faculty members alike as students reflected on their varying amount of years at the school. Not all speeches were sad, though, and some even utilized humor as their main method of reflection.
"I'm going to take a passage from the Lord of the Rings and twist it to fit my needs," said McKenna Morey Bovey; she was not the only student to use a passage or quote from Lord of the Rings, although she was the only one to alter its contents.
Some students chose to say things to teachers that they never had a chance to before.
"It isn't easy to read the long books for homework... I am a native Chinese speaker and I never had the patience to read a book in Chinese, and you want me to read it in English now? Be realistic," said Yuhao Chen to a wave of laughter.
Prior to the speeches from students and Wilson, there were special awards given to students, faculty members, and other important people to the community.
The first award was the Student Council Barb West Award, presented by Julia Lees to a student that she thought had "immersed himself in the school community." The award was given to Rocky Yee, a non-graduating student.
Courtney Callo presented the Student Ambassadors Debby Brown Award to graduate Parker Lyman.
"He shares the true love of Long Trail," said Callo, "and he has donated hours of personal time [to the school]."
National Honor Society Advisors Todd Smith and Kelley Swarthout were next to award the National Honor Society Dave and Rene Wilson Award to Julia Lees. The presentation left Swarthout choked up.
The Founder's Award, "Honoring the spirit of community service of Dave & Rene Wilson," was presented by the President of the Long Trail Parent Association, Margaret McChesney.
"This person most closely exemplifies the dedication of the founders," said McChesney before listing a series of words she thought described the winner, including "New Yorker... Faculty member... Glue... Sagitarius... Endless, boundless energy... [and] the most positive person." The award was given to Patty Alexander.
Nelly Birch was given the next award, the Pay it Forward Forbes Award, by Sally Leonard, who became emotional while describing why she thought Birch was the best candidate for the award.
The Dorothy Peirce Faculty Award, presented by Melissa Chestnut-Tangerman, was awarded to science teacher Scott Worland. Tangerman outlined why he was receiving the award, which included his experiments with releasing weather balloons, and retrieving them after. The final award, the Long Trail School Citizen of the Year, was presented by Steven Dear and given to Gerrit Kouwenhoven, the chairman of the Board of Trustees.
Throughout the ceremony, there were various breaks for musical performances. Graduate Vanesa Mae, accompanied by Geoffrey Gee, performed "For Good" from the musical "Wicked," which included lines such as "Who can say if I've changed for the better?/But because I knew you / I have been changed for good."
Later, the US Chorus performed African American gospel song "Glory Glory," and the IB Music Ensemble performed Chick Corea's "Spain." After the class recessional, to Kansas' "Carry on My Wayward Son," attendees were invited to a reception area for refreshments and cake and a chance to congratulate the new graduates.