The story of Greens Farms Academy begins with "Mrs. Bolton's School for Girls," founded by Mary E. E. Bolton, “an English lady of education and culture." In the summer of 1925, Mrs. Bolton "visited Westport and feeling the charm of the town decided that it would be an ideal place to establish a private school for girls determined that [the students] should be educated on the models of the best English schools...." The other original teacher was Mrs. Bolton's younger sister, S. Kathleen Laycock, who arrived in Westport in 1926. In October 1925 Mrs. Bolton leased a room for her School, as well as living space for herself and her two daughters, Elizabeth Mary and Ann, in a three-story frame house on Church Lane across from Christ and Holy Trinity Church. The School began with four students, but by the spring of 1926 the enrollment had increased to eighteen students aged seven and under. The space on Church Lane was already too small. 

Mrs. Bolton then rented a large Greek Revival house owned by Willard S. Adams on the corner of East State Street (Post Road East) and Ludlow Road, where classes were held from 1926 until 1929. Enrollment continued to grow during the three years at the Adams property - in a very controlled way. No children were admitted who were older than Betty Bolton. As she grew, the School added a new grade each year until 1935, when Betty was a senior and the School spanned pre-Kindergarten through Twelfth Grade. A few boys up to the age of eight attended, usually boys with sisters at the School. Mrs. Bolton also took on a few boarding students, as space permitted, and from time to time boarded girls while their parents were traveling. 

The School moved again in 1929 to the northeast corner of the intersection of King's Highway and Wilton Road (present location of the Willows Medical Center.) For the next thirty years Mrs. Bolton, Miss Laycock, and their small faculty tutored young ladies in the large Victorian farmhouse and its three buildings overlooking the Saugatuck River. By the late 1940s and early 1950s The Bolton School was well established in the Westport area. It was known to have educated its students well and it had an excellent record in placing students in good boarding schools and colleges.

By the mid-1950s, however, the old house, barn, and sheds of the King's Highway property were dilapidating fire-traps. Mrs. Bolton's lease was nearing an end, and the owner of the property wished to sell. A group of concerned parents and friends of the School, including Lucie Bedford Cunningham (later Mrs. Lynne A. Warren) and John D. Upton, began to worry about its future. They approached the sisters with the idea of incorporating The Bolton School as a not-for-profit institution, which could then raise money to build or buy new facilities. Mrs. Bolton declined, preferring to retain ownership of her Nursery School and Lower School, but Miss Laycock, Headmistress of the Upper School, agreed. 

On October 22, 1957, The Kathleen Laycock Country Day School, serving students from Sixth through Twelfth Grades, was incorporated. It had no endowment, it had no home, and, for two years, it continued to operate in the old Victorian house just as before. The only new aspect was that the upper-school pencils read 'KLCDS' and the lower-school pencils read 'Mrs. Bolton's School'

The search began for a new property with existing buildings requiring minimal renovation. The R. T. Vanderbilt estate on Beachside Avenue - with  more than 27 acres, including frontage on Long Island Sound - was available for $325,000.

"We had zero money, so that looked awfully heavy, even though in today's terms it's an absolute steal," said John D. Upton, one of Laycock's founding trustees. He went to the Vanderbilt family and since the School did not need or want the most valuable waterfront section, suggested the property be divided so that the house and approximately 26 acres north of Beachside Avenue could be purchased by the School for $250,000. The deal was struck. 

The Vanderbilt house sat in an area of Greens Farms owned largely by the Bedford family. Deacon F. T. Bedford (1823-1904) purchased a large farm there in 1861. He and his two sons, Edward T. Bedford (1849-1931) and Frederick H. Bedford (1854- 1930), cultivated onions and strawberries as cash crops. The Bedfords prospered in business as well as agriculture; Edward T. Bedford rose through the ranks at the Standard Oil Company to become a director and member of the executive committee. Edward's son Frederick T. Bedford (1878-1963) - father of Lucie B. Cunningham Warren, a founding trustee of KLCDS - continued the tradition as both a successful businessman and a country gentleman. The Bedford family had a long history of philanthropy in Westport, having donated substantial amounts of real estate and development funds to build the YMCA, fire stations, elementary and middle schools, athletic fields and parks, and the former state police barracks. 

First Frederick T. Bedford, then his father Edward T., constructed large mansions along Beachside Avenue on the shore of Long Island Sound. Edward's younger brother F. H. Bedford built his house farther west on the north side of Beachside Avenue overlooking New Creek and Burying Hill. When F. H. Bedford's daughter Mildred married Robert Thurlow Vanderbilt (1885-1954), F. H. built them a large summer house next to his own. 

R. T. Vanderbilt, a distant cousin of Cornelius Vanderbilt, grew up in Brooklyn where the F. H. Bedford family also maintained a residence. In 1916 he founded the R. T. Vanderbilt Company of Norwalk, producer of mineral and chemical additives. The three sons of R. T. and Mildred Bedford Vanderbilt enjoyed summers and vacations on Beachside Avenue near their grandfather. After Grandfather F. H. died in 1930, a storm damaged buildings on the property and both the Bedford and Vanderbilt frame houses were torn down. In 1934, Mr. and Mrs. Vanderbilt commissioned architect Harrie T. Lindeberg (1879-1959) to design a new country residence. Mr. Lindeberg, who in his youth apprenticed with McKim, Mead, and White in New York, had a residential client list like a page out of Who's Who. Armour, Astor, Doubleday, DuPont, Pillsbury, to name a few. An architecture critic of his era said of Lindeberg's houses, "To analyze them is to be impressed by their practicality and at the same time by their interesting character.... They exhale so much ability and taste. They exhale so much beauty." 

For the Vanderbilts, Architect Lindeberg produced an English-American stone house set on a hill amidst an apple orchard with a sweeping view of Long Island Sound, the main building of Greens Farms Academy today. In many of the rooms, he used 18th-century English and Colonial American paneling, only some of which survived the transformation of the building into a school. "It was really a very elegant place - no question about that." 
In 1939 Mr. Vanderbilt engaged the renowned landscape architect Ellen Biddle Shipman to design a planting scheme for his entire Beachside Avenue property. Between the two World Wars, Mrs. Shipman was a favorite of the moneyed industrialists who were building large country homes across America. An article in the New York Times, February 7, 1997, reported that Shipman saw "the garden as intimately connected to the lines and feel of the house, but her taste lay more in the direction of the Colonial garden, with its simple rectangular lines and artful combinations of plants that blended gradually into the surrounding landscape...." Mrs. Shipman's garden designs included walls, paths, and fountains as well as colorful, fragrant, and varied perennials blooming in succession. The School's main library and 1994 Arts and Academic Wing now form two sides of the main garden designed by Ellen Biddle Shipman in 1939-40. 

Over the summer and early fall of 1959, the Vanderbilts' country home overlooking Long Island Sound was modified to accommodate The Kathleen Laycock Country Day School. On Monday after Thanksgiving vacation in 1959, nine faculty members and 71 students, Grades Six through Twelve, moved to 35 Beachside Avenue. In 1960 Mrs. Bolton's Grades One through Five also moved to Beachside Avenue; Laycock added its Kindergarten in 1965. 

With KLCDS in "very lush, very English'' new quarters, growth of the program and the student body could begin in earnest. Miss Laycock had retired in 1963. Her successor, William M. Posey, undertook an ambitious expansion of the facility, adding a large auditorium/gymnasium, cafeteria, and classroom wing to the School. By 1966 under Headmistress Nancy Lauber, Bolton Class of 1951, The Kathleen Laycock Country Day School boasted an enrollment of 250 and a faculty of 30. Increased enrollment and the addition of the Kindergarten led to construction of another lower school classroom building in 1967. Small additions and renovations as well as expanded art and athletic facilities were added through the 1970s. 

By the end of the 1960s, a new issue arose. Single sex institutions of all kinds were merging, closing, or opening their doors to the opposite sex. In 1969, after a year of study and deliberation over various options, the School's Board of Trustees decided to admit young men into the Upper School in the fall of 1970 and into all grades in the fall of 1971. Headmistress Nancy Lauber wrote, “We believe that the different academic interests and viewpoints of boys and girls will cause the elective courses to increase in size and balance and will, therefore, provide a more stimulating academic atmosphere for students and faculty members. The extra-curricular program and the social activities of the School will also be strengthened. More and more of our graduates will attend coeducational colleges, and all live in a coeducational world."  

Believing that it would be difficult to attract boys to "Kathleen Laycock Country Day", the trustees also renamed the School, so that, in September of 1970, 23 young men joined approximately 300 young women on the opening day of Greens Farms Academy. 

For the next ten years the Academy settled into coeducation and both broadened and deepened its academic, athletic, and extra-curricular programs under the leadership of James M. Coyle, who became headmaster on July 1, 1972. By 1980 student enrollment had reached 406, and again architects and construction equipment descended upon 35 Beachside Avenue. Architect Mark Thompson of Philadelphia began a long, productive relationship with the School designing additions and renovations which incorporated graceful elements from the original residence into the economical and utilitarian spaces required by a growing school. 

Added in succession were the Jillian Scholy Coun Library in 1981, the Bernhard Academic Wing in 1982, which included the EC Home, common room, middle and upper school science laboratories, and a new boys' locker room. In 1987, GFA added the Lynne A. Warren Lower School wing, in 1988 the Lucy B. Warren Middle School Wing, with its signature feature, the Taylor Forum and the 1994 Arts and Academic Wing.

Another round of additions occurred in 1997, including new classrooms, a language lab, a new computer room, expanded library and arts facilities, and a large gymnasium named after headmaster, James M. Coyle, who retired in June 30th, 1998. After 26 years at the helm, in August, 1998, Peter T Esty became the sixth head of Greens Farms Academy. After his departure in July, 2003, renowned educated Janet Hartwell, formerly of the Groton School, became the seventh head of school GFA. 

Today, GFA is a PreK through 12 co-ed day school with over 700 students, three gymnasiums, advanced technology, a black box leader, electronic music labs, and on and on. In 2018, Bob Whelan became GFA's eighth head of school. Mrs. Bolton and Ms. Laycock would be very astounded... and pleased.