1963-64: Joseph Kemp and George Crawford, supervising principals at Arcade and Delevan-Machias central schools respectively, first discuss merger. Initial joint meeting of the two school boards held.
1965: State legislature passes legislation making it attractive financially for school districts to merge. Franklinville briefly considers becoming part of three-way merger.
1966: Joint meeting of Delevan-Machias and Arcade school boards yields green light for merger. Claris Persons of Delevan named chairman of joint boards. State gives approval to merger plan. In voting held May 31, merger is approved 1,404-663. New nine-member board elects Verne Goodemote of Chaffee as first president. George Crawford named district principal. "Yorkshire-Pioneer" chosen as official name of district.
1967: District voters approve $70,000 purchase of 78 acres of Steve Smith farm between Old Olean Road and County Line Road, Yorkshire. Architectural firm Fenno, Reynolds & Jones hired to design new junior-senior high school. Voters approve plans for $4.6 million facility. School board okays use of electric heat at school, leading to citizens group opposition and lawsuit.
1968: Board asks voters to approve additional $525,000 for completion of high school; measure is initially defeated but later passes when $100,000 is cut. Excavation begins on building site, followed by construction.
1969: St. Pius X School in Delevan closes in May, accenting the urgency with which the new school is needed. Though construction on high school is not complete for September opening, students and staff work together to survive the debut. Senior class has two sets of officers and advisors.
1970: New 1,200-seat auditorium hosts April dedication of Pioneer Junior-Senior High as well as June commencement.
1971-72: Need for middle school becomes apparent to school board. Architect Gordon Jones hired to draw up plans. George Crawford retires as superintendent, succeeded by Dr. Harry Packer.
1973: Voters approve $5.2 million middle school plan.
1974: Ground broken for middle school.
1975: Pioneer Middle School opens, having been paid for in advance thanks to generous incentive aid from the state.
1976: Committee of 44 formed as result of concerns about drug use and alleged lack of discipline at high school. Lengthy contract dispute erupts between school board and Pioneer Faculty Association.
1977: School criticized for its handling of Blizzard of '77. Dr. Harry Packer terminated in favor of Henry Heslop, who remained superintendent for 13 years.
Late 1970s - Early 1980s: Using incentive aid, Pioneer moves to modernize and expand its facilities.
Mid-1980s: Failure of Lion Capital Group causes significant investment loss for Pioneer.
1990: David Kurzawa, Pioneer administrator since 1981, is named superintendent after retirement of Henry Heslop. District's use of technology begins to grow extensively.
1997: Pioneer drama/music departments win prestigious Kenny Award for "Over Here!"
2001: District gathers to mark 35th anniversary.
2007: First capital project is completed, bringing new turf stadium to HS, Ag barn at HS, Large group instruction at MS
2016: Second capital project is completed, resulting in new science & performing arts wings at HS, upgrades at Arcade Elementary