Cushing Academy is a private, coeducational college-preparatory school for boarding and day students in Ashburnham, Massachusetts, United States.

[3] Following a provision from his will, the money accumulated for ten years before a board of trustees applied for an act of incorporation.

On May 15, 1865, the Great and General Court of Massachusetts granted a charter, and the Academy opened in 1875 on land formerly known as Bancroft Farm.

[4] A statue, the Schoolboy of 1850, honors both students and, more specifically, boys who fought in the Civil War.

It was designed by Bela Pratt and was donated to Ashburnham by local businessman Ivers Whitney Adams in 1913.

[4] In 2009, Cushing made headlines for its plans to spend $500,000 transforming the Fisher-Watkins Library into a learning center with e-readers, e-book database subscriptions, flat-screen televisions, laptop-friendly study carrels, and a coffee shop.

[4] In October 2017, the board of trustees announced that Randy R. Bertin, Ed.D., of Besant Hill School in Ojai, California, was unanimously appointed the 13th Head of Cushing Academy, effective July 1, 2018.

[23][4] Cushing offers courses in classical and modern languages, computer science, English, history and social science, mathematics, performing arts, visual arts, and support services such as English as a second language and academic support.

[4] Cushing has a long hockey tradition that began in the early 1900s, though the boys' team in its present form has only been around since the 1980s.

[27][28] As of 2018, Cushing has dozens of teams in the following sports: cross country, field hockey, soccer, skiing, football, volleyball, basketball, ice hockey, baseball, golf, lacrosse, softball, tennis, and track & field.

Cushing's annual Mountain Day tradition began in 1926 in honor of Cowell, the third principal.

During World War II, Mountain Day was held at the nearer Mount Watatic for a few years due to gas rationing.