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- Freeport's first public school started in a one room school house located at the north end of the triangle formed by the intersection of Main and Church Streets
- 37 students attended school six days a week. On Sundays, the Presbyterian Church held religious services in the school building
- Professor McGee introduced grammar, geography, natural philosophy and an advancement in mathematics. He also introduced the blackboard
- A new one-story school building was constructed on Main Street's west side, slightly north of Merrick Road
- After repeated and unsuccessful attempts to get a bigger school built, a few local residents took matters into their own hands and demolished the old building. While the new school was being constructed, the district rented space from Andy Rhodes' wagon shop for three months. Rhodes was paid $8. The original building was sold to Mr. Daniel Ellison for $50.
- 203 students enrolled. Total expenses for the year: $414.63
- New building on the northwest corner of Pine Street and Grove Street is constructed for $3,858.75. Old structure is sold for $750
- Uniform system of textbooks introduced
- Caroline G. Atkinson hired as Freeport's fourth teacher (in addition to L. M. Burdick, Phebe Tice, and Louise J. Carpenter). Ms. Atkinson was a graduate of Albany Normal School (University at Albany)
- Thomas H. Wheeler becomes a teacher in the Freeport School around 1858
Wheeler, Thomas H.
- (October 7) A motion was passed changing the District School to a Union Free School
- Enrollment reached 528. Charles W. Oley became principal
- (March 9) Formal opening of the new school located on the corner of Pine and Grove Streets
- (October 11) High school grade formally began
- First high school class graduated
- Large addition added to school building costing approximately $30,000
- New school building constructed at the corner of Ocean and Seaman Avenues
- The Girls' Athletic Association with the Help of the Board of Education were able to get a tennis court constructed on school grounds
"School Notes." Nassau County Review. June 17, 1910, 1. Accessed October 29, 2018. http://nyshistoricnewspapers.org/lccn/sn95071433/1910-06-17/ed-1/seq-1/.
- Students population by school: Seaman Avenue School, 259 pupils; Archer Street School, 225 pupils; Grove Street School, 519 pupils
"School Notes." Nassau County Review. September 9, 1910, 1. Accessed June 19, 2019. http://nyshistoricnewspapers.org/lccn/sn95071433/1911-05-05/ed-1/seq-1/.
- (May 1910) Over a four week period, 125 students were absent due to an outbreak of measles
Freeport Board of Education Minutes, May 16, 1910.
- Due to school overcrowding, many students placed on part-time schedules. Rooms rented in the Village to provide classroom space
- Caroline G. Atkinson appointed acting school superintendent. She was the only female superintendent on Long Island
"Our School Superintendent." Nassau County Review. January 19, 1912, 8. Accessed July 26, 2022. http://nyshistoricnewspapers.org/lccn/sn95071433/1912-01-19/ed-1/seq-8/.
- Columbus Avenue School constructed
- Flashings, the Freeport High School newspaper, began
- Continuation classes started by the Board of Education for minors 14 and 15 years old who went to work before graduating. Class took place on Saturdays between 8 a.m. and noon
- Freeport Cemetery chosen as the site for a new school building
- Grove Street School overcrowding made it necessary for the district to use space in the neighboring Engine Company No. 1 firehouse, the Presbyterian Church, the Library, and YMCA
- Junior-Senior high school enrollment reaches 887
Dodd Retiring as Freeport School Head. Newsday. December 14, 1960, 30.
- First known published usage of "Red Devils" to describe an athletic team from Freeport High School
Huley, Frank. "Freeport Beats Hempstead Hempstead with Final Spurt 18-15." Nassau Daily Review. December 18, 1933, 12. Accessed August 7, 2018. fultonhistory.com
- Cleveland Avenue School opened
- Columbus Avenue School enlarged
- Roy Leon Smith, former principal of Freeport High School, died at his home in North Adams, MA. He was 51 years old
- Junior-Senior high school enrollment skyrocketed to 1,779. Grove Street Elementary School begins housing the 7th grade
- School District publishes a 45 page booklet entitled The School Building Needs of Freeport, Long Island
- Dr. Dodd re-elected president of the New York State Teachers Association
- Willard W. Jones, principal of Archer Street School, entered the Army as a chaplain. Dana H. Smith succeeded Jones
- Bertha Hull, principal of Seaman Avenue School retired. Lawrence C. Lobaugh succeed Hull
- Helen E. Ross promoted principal of Columbus Avenue School after the retirement of Augusta M. Lovenguth
- Long Island Park Commission gives nine acres of land north of the Cleveland Avenue School to be used as athletic fields for Freeport High School
- Atkinson School constructed. This school was named for Caroline G. Atkinson, a teacher with over 50 years of service in the school district
- Seaman Avenue School used as temporary school housing for over-flow classes
- Freeport High School teachers K. Alice Hoerner and C. Sheard Parker died in a plane crash. They were returning from summer vacation in upstate New York were they both had homes
- Buffalo Avenue Field House was constructed for the athletic field north of the Cleveland Avenue School
- Freeport High School constructed on the marshy land between the Village of Freeport and Baldwin
- (April 30) Dodd Middle School is dedicated
- (January 14) Leo F. Giblyn School dedicated
- Freeport leased classroom space from the First Presbyterian Church for 209 first and second graders while $60,000 in renovations were made to Archer Street School
"Church Leases Space to Archer School Students." The Leader. October 14, 1965, 13. Accessed June 1, 2018. http://nyshistoricnewspapers.org/lccn/sn95071064/1965-10-14/ed-1/seq-15/.
"Jewish Group Objects to Church-School Ties." Newsday. November 5, 1965, 15.
- Seaman Avenue School was converted to an administration building
- Athletic field at Freeport High School was named in honor of George Emma
Benza, A. J. "Keening a Coach's Memory Alive." Newsday. January 3, 1988, 27.
- (October 7) Fire burned the Grove Street School
- Addition added to Freeport High School
- (April 21) March of Dimes, Nassau County Department of Health, and the Freeport Public Schools held an immunization clinic at Columbus Avenue School for rubella (German measles). Vaccinations for rubella became mandatory for New York State school children in 1970
Planning Immunization Day. The Leader. April 15, 1971, 14. Accessed May 11, 2022. http://nyshistoricnewspapers.org/lccn/sn95071064/1971-04-15/ed-1/seq-14/.
- Freeport High School football team returned to Freeport Stadium after six years of playing at Hofstra University while the Stadium was undergoing renovations.
"FHS Football Back to Stadium." Village News. Freeport: NY. November 1974, 1.
- (September 29) - John W. Dodd Junior High School, Phase I Addition Dedication
- District celebrated its centennial
- Flashings, Freeport High School's newspaper, fought censorship over an article it wanted to publish about the arrest of the track coach
- New Visions School of Exploration & Discovery, Freeport's first magnet school, opened
- Archer Street celebrated 100th anniversary
- (October 6) Elinor Smith was awarded a Freeport High School Diploma posthumously
- Columbus Avenue School and Archer Street School are given historic roadside markers by the Freeport Landmarks Preservation Commission
- Freeport High School football team won the Long Island Conference One championship