1920
Reverend and Mrs. Frank Bigelow founded The Rectory School in the rectory of Christ Episcopal Church, Pomfret, CT. The Bigelows established the school because their son, John, was not receiving the education necessary to prepare him for secondary school. John was joined in his studies by a neighbor, George Chandler Holt.  By 1921, six students were enrolled. 
 
1922-1923
Greystoke, a vacant building on the north side of Christ Church, was acquired to accommodate growing number of boarding students.  

1924
Father Bigelow formalized the school and developed a structured program, which challenged junior high school students intellectually, guided them morally, inspired them artistically, and encouraged them athletically. The program also emphasized self-discipline and independent thought. Seventeen boys were now enrolled in the school.

1925
In the spring, Greystoke burned to the ground. Fortunately, no one was injured, but the publicity about the fire resulted in publicity about the school. John Bigelow later recalled a sharp increase in enrollment the following year.  After the fire, the Bigelows rented Out of Bounds (now owned by the School) as a dormitory. In the fall, they acquired over 100 acres and the Grosvernor house, a large home across the road, with financial backing of a Christ Church parishioner.  That house is now Main House, on Rectory's front circle, and the land is the site of the campus, which now encompasses 128 acres. In September, 1925 Rectory opened on its present site with 36 boarding students.

1929
A dining hall was constructed (by the old Putnam Trade School) consisting of two floors of dormitories over the dining and kitchen areas.

1935
Rectory was incorporated as a non-profit organization with a self-perpetuating Board of Trustees, thus ending Rev. Frank and Mabel Bigelow's personal ownership of the school. An old barn was converted into a small gymnasium, sports fields were landscaped, and three tennis courts were built along with two cottages and several outbuildings.    

1937
John Bigelow (Mr. John) became Headmaster. Mr. John developed the one-to-one tutoring program, known today as IIP, to serve children with dyslexia, pioneering the use of the Orton-Gillingham method of remedial training.

1940s- 1960s
IIP offerings were expanded to meet the growing academic needs of students – from remedial to gifted learners.  Secondary School Placement guidance was formalized to ensure the continued academic success of each Rectory School graduate.  Sports teams and clubs were added.  Overall enrollment increased as Rectory grew more recognized as a highly personalized academic experience for all types of students.    

1974
Mr. John Bigelow retired and Mr. John Green became head of Rectory. Mr. Green led school facility expansion and formalized the Individualized Instruction Program (IIP) to include underachievers and students with a wide range of mild learning disabilities.

1980s
The new academic building and Colhoun Gymnasium were opened. 

1990s
In 1990, Mr. Thomas F. Army became Head. The warm, nurturing community was reaffirmed. The education was broadened to include new math and science curricula, foreign language, expanded programs in fine and performing arts, athletic participation, community service, and March Experiential Learning Program. Technology was updated. Long Range Capital Program commenced. The new science wing was added to the academic building.

1994
Rectory was recognized as a “School of Excellence” by the U.S. Department of Education Blue Ribbon Schools Program    

1996
John Brittain Bigelow Academic Building was renovated, and the science facilities and Day Room, a gathering place for non-boarders, were added.

1998
Construction of Hamilton North-South Dormitory was completed.    

1999
Renovation of the former Chapel/ Assembly Hall into the new Day Care facility was completed.

2000
The Perkins addition to the Hettinger Library was completed.    

2001
The Main House was renovated, and construction of the Kinmay and P. Y Tang Performing Arts Center and Auditorium were completed. Construction began on the new maintenance facility.

2002
Construction was completed on the new Dining Hall and the maintenance facility.    

2003
Construction of the Collins Art Barn was completed.    

2004-2005
Rectory's Elementary School, led by Director Maria Carpenter, began with a kindergarten class.

Due to overwelming success they began planning to add a grade each year until it became K though 4.
    
2007
For the first time in Rectory's history, female boarders were accepted. Fisher Cottage and Out of Bounds were remodeled to accommodate six girls each and apartments for the dorm parents.

2008
We had a wait list for female boarders! Faraway, formerly a faculty residence, was remodeled to house six female boarders and two dorm parents.
The first group of fourth graders became fifth graders in the Middle School, marking the completion of K-9th grades at Rectory.
Renovation began on the lovely Deal House, which is south of the Academic Building. Several departments will reside there, including Alumni, Development, and Foundation. A walkway meandering though the trees was installed to connect the two buildings.
Mr. Army announced the new nickname for the School: The Rectory Oaks.

Click Here to read about the appointment of Rectory's new Head of School, Frederick W. Williams, effective July 1, 2009.