Early 1860s - Eliza Burnett Fay and her sister, Harriet Burnett, establish a day school.
1866 - Fay School officially founded. The School opens with two boarders and five day students, who attend classes in the Unitarian Parsonage (now Todd House, across the street from the present campus). The boarders live in the Greenwood House, which later forms the nucleus of the Old Main Building.
1877 - The School moves to larger quarters above the Center Store/Post Office next to the Greenwood House.
1885 - A wing, comprising a 32-bed dormitory, a study hall, and classrooms is built onto the Greenwood House.
1889 – The School’s first gymnasium is constructed (now called the Upjohn Building, named for Richard V. Upjohn, faculty member emeritus, and used as a multi-purpose space).
1893 – The school building is enlarged to include music room, recitation rooms, and additional dormitory space. Fay’s first tennis courts are constructed.
1896 - Eliza Burnett Fay dies. Waldo B. Fay, class of 1871, becomes headmaster.
1897 – Fay purchases Senior Field, located on Middle Road.
1908 - Dormitories and a large schoolroom are added, as well as a library. School comprises 77 students and seven masters.
1910 - Edward W. Fay, Waldo’s son and a member of the class of 1898, starts teaching at the school.
1914 - Additional property is purchased on Main Street. The School now owns three house lots on Main Street, as well as sizeable land holdings from Route 30 to the reservoir.
1917 - Fay House is purchased by Waldo Fay as a family residence.
1918 - Edward W. Fay '98 succeeds his father as headmaster.
1920 - Fifth form (grade seven) is added. An outdoor ice skating rink/swimming pool is constructed.
1922 - Fay School is incorporated, and the first Board of Trustees is appointed. Waldo Fay transfers ownership of the School to the Board. Adjacent properties of Winchester Tavern, Center Store, and Goodnow House purchased.
1926 – The Dining Room Building is constructed on the site of Winchester Tavern. The Dining Room is given by the mothers of boys who attended the School between 1896 and 1918, and named for the wife of Waldo Fay, Mary Winchester Fay.
1927 – The School comprises 93 boarders and three day students.
1938 –Fay published the first issue of its Alumni Bulletin.
1940 - Waldo Fay dies. By forgiving the mortgages and loans owed by Fay School, he effectively gives his family's entire interest in the School to the Board of Trustees.
1942 - Harrison L. Reinke becomes Fay's fourth headmaster, and the first headmaster at Fay in its 76-year existence, who is not a member of the Fay family. The Pioneer, Fay’s school newspaper, is founded.
1945 – Brackett House, located at 31 Main Street, is given to the School by Henry U. Harris '13.
1956 - The Henry U. Harris Building, which provided classrooms for the Lower School and an additional gymnasium, is dedicated. Webster House is purchased.
1962 - Waters House is purchased.
1963 - Edward W. Fay dies, leaving Fay House to the School. East House is purchased.
1966 – The Fay community contributes over $1 million to the School's Centennial Fund. Henry U. Harris ’13 retires as Chairman of the Board. The School purchases South House, North House, and three acres adjacent to the reservoir.
1969 - A. Brooks Harlow, Jr. '49 succeeds Harrison L. Reinke as Fay’s fifth headmaster in 103 years. Ninth grade is added to the School.
1970 – The Harrison L. Reinke Building is dedicated.
1972 - Previously open to boys only, Fay admits twelve female day students.
1974 - Trap House, donated in memory of Philip D. Holden '23, is dedicated.
1976 – The Upjohn Building is moved to the site behind Fay House.
1977 - Fay School becomes fully coeducational. Construction on Steward Dormitory begins.
1978 – The American Language Academy opens a branch at Fay School for the tutoring of international students. Campbell Steward Dormitory is dedicated. Fay’s enrollment stands at 278.
1979 - Parkerville Field is purchased.
1984 – The Fay community raises $1.25 million to build a new main building, the Root Academic Center.
1986 – The Old Main Building is razed.
1987 - The Picardi Art Center and the Boylan Stair Tower are dedicated.
1988 - Fay's International Student Program (ISP) replaces the American Language Academy for the purpose educating non-English speaking international students. Stephen V.A. Samborski succeeds A. Brooks Harlow, Jr. '49 as Fay’s sixth headmaster.
1990 - Stephen C. White becomes Fay's seventh headmaster. The first issue of Fay Magazine is published.
1991/92 - Fay School receives the Blue Ribbon Award from the U.S. Department of Education.
1993 - Harlow Gymnasium is dedicated.
1994 – The MacAusland family names a playing field on Parkerville Road in memory of Donald MacAusland '31.
1995 - The Harris Events Center and Mars Room are dedicated. The new music center opens.
1997 - Fay's first gymnasium, built in 1889, is dedicated in honor Richard V. Upjohn, faculty emeritus, and renamed the Upjohn Building. The kitchen is dedicated in honor of Lewis Maida, the school's chef from 1957 - 1997.
1999 - John and Adrienne Mars challenge the Fay community with a $5,000,000 gift to Fay’s endowment.
2001 – The new wing of the Root Academic Center opens, adding the Learning Center and science and mathematics classrooms.
2003 - The Adrienne B. and John F. Mars '49 Wing of the Root Academic Center is dedicated. Enrollment stands at 382.
2005 - Jay and Ting Fields are dedicated.
2006 - Fay purchases the Ceramicole estate, now known as West Campus, including the Kidder Mansion. The entire academic campus is now 26 acres.
2007 - The house at 74 Main Street, now the residence of the head of school, is purchased.
2008 – Robert J. Gustavson, Jr. succeeds Stephen C. White as Fay’s eighth head of school. Fay also adds a new athletic campus, formerly the Marlborough Equestrian Center. The Fay School campus is now 66 acres.
2009 - Two new dormitories, now known as the Village Dormitories, open for Fay’s boarders. Fay earns the U.S. Green Building Council’s LEED Certification at the Gold level for these buildings.
2010 – Fay opens its new Primary School on Middle Road, which incorporates the historic Goodnow House with a state-of-the-art “green” facility for Pre-Kindergarten through grade two. The new Wellness Center opens on the ground floor of the Steward Dormitory.
2011 – Fay launches One School, One Book, an innovative literature project where all students in the Lower School read and discuss the same novel in discussion groups along with parents and teachers.
2012 – Grade six becomes the oldest grade in the Lower School, so that Fay’s divisions are composed of Primary School (Pre-K through grade 2), Lower School (grades 3-6), and Upper School (grades 7-9). Fay completes extensive renovations on the second floor of the Root Building to upgrade the Lower School classrooms, and Lower School teachers refine their curriculum. Fay also launches a new athletics program designed especially for grades five and six that integrates instruction and interscholastic competition.
2012 – Fay launches iPad pilot project, issuing iPads to every ninth grader and embarking on extensive professional development for teachers integrating the new technology.
2012 – Fay welcomes 120 boarders to the Upper School—a record number of boarders—who hail from 21 countries around the world.
– Fay introduces a competitive and instructional squash program in concert with Dover Squash Academy as a winter term sports option. Fay now offers 20 sports (with 41 different teams) for Fay athletes over the course of the year.2014
- Fay opens the Innovation Center for technology, engineering, and design thinking. The 3,000 square-foot lab space, which is open to Fay faculty, staff, and students from Pre-K through ninth grade, includes a maker space, fabrication lab, video production facilities, audio recording studio, and wood shop.