Bridgehampton Union Free School District

Bridgehampton's first public school was the Two Chimney Schoolhouse, opened in 1720.[1][7][18] The building was located at Bull's Head – later known as Triangle Common – the intersection of what is now Montauk Highway and the Bridgehampton-Sag Harbor Turnpike (about 0.5 miles (0.80 km) from the current school building).[7] In 1820, Southampton Town school commissioners Abraham Rose, Rufus Foster, and William Herrick laid out school districts for the town; Bridgehampton became District #9, and moved two a new building on the same site. This building was used until c. 1842.[7] The next schoolhouse was sold in an August 1907 action to Herbert Hedges, who moved the building to Wainscott, where it now stands as a chapel and community center.[19]

In 1907, the newly-formed Bridgehampton Union School District voted to build a new school on a new site off Church Lane.[1] The new two-story building opened as a middle school on January 6, 1908, adding a high school program two years later.[1] In 1911, the district became the Bridgehampton Union Free School District and graduated its first student.[1] This school was later known as the "School Street School" due to its location at the corner of Church Lane and School Street, the current site of the Bridgehampton Fire Department.[18]

Outgrowing this facility, construction broke ground on the current Montauk Highway building, the area's fifth school building, in September 1930.[1] The building was designed by the architectural firm Tooker and Marsh and opened in 1931.[18]

For a period that lasted through most of the 1990s, the school had a primarily African-American enrollment,[20] but a 2004 New York Times article detailed large demographic changes in the community and the school.[21]

Due to its small size, some have proposed that the high school portion of the school should be closed and students sent to larger nearby high schools in adjacent districts.[12] A ballot to close the high school during the 1987-88 school year narrowly succeeded, but was later overturned.[13] A 2009 initiative was also defeated.[14]

In 2003, the district signed a contract with the nearby private Ross School to provide breakfast and lunch at a cost of $3.12 per student. The district does not have its own kitchen. It was the first public school-private school partnership for school lunch in New York State.[22]

A $29.4 million extensive renovation and expansion of the school was approved by voters in December 2016. The expansion was to add over 35,000 square feet (3,300 m²) to the existing 30,000-square-foot (2,800 m²) building and was originally expected to be completed by December 2020.[23] The project included a new gym and athletic facilities, new cafeteria, new technology room, renovated library, and renovated classrooms.[24] Construction was delayed due to the COVID-19 pandemic, but some renovated classrooms were available for use in the second half of the 2020–2021 school year. The project was fully completed in time for the 2021–2022 school year.[25]

Mary Kelly, the current superintendent was appointed in May 2021. She was nominated to succeed Robert Hauser, who had previously been superintendent since February 2018, and assistant superintendent prior to that.[26] Kelly's appointment was challenged by the NAACP Eastern Long Island branch, citing an incident in her prior superintendent role at the Amityville School District.[27]

In April 2023, the district announced that Assistant Principal Michael Cox would become principal effective July 1, 2023. This followed the announcement that current principal Michael Miller, would be moving to the Superintendent/Principal role at East Quogue Union Free School District.[28]