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The first graduating class was composed of five girls who graduated in 1866.
In 1906, a new school was built adjacent to the old one on North Church Street.
In 1923 a stadium was built on Penn Street and stands to this day.
In 1923, the Student Council was created to help students and staff work together.
In February 1951, the West Chester Joint High School was opened at the school's current location on Montgomery Avenue.
In 1954, a junior high occupied east side of the building, but became part of the high school after growing enrollment.
Consolidation of the West Chester Area School District was finalized in July 1966 as the final touches were placed on West Goshen Township’s newest school – Glen Acres Elementary.
Although construction was approved and overseen by the West Goshen School Board, the newly formed West Chester Area School Board presided at the dedication on January 15, 1967.
In 1968, the school was renamed B. Reed Henderson High School after the longest serving principal of any high school in the district.
The school received a generous addition in 1996-97 which houses a new gymnasium, an art room, two music instruction rooms, two small group instruction rooms, a large group instruction room, and two additional classrooms; all located on the East side of the original building.
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| Company name | Founded date | Revenue | Employee size | Job openings |
|---|---|---|---|---|
| Roncalli High School | - | $7.1M | 150 | - |
| Comsewogue School District | - | $13.0M | 350 | - |
| Alpena Public Schools | - | $20.0M | 350 | 46 |
| Glynn County Schools | - | $17.0M | 350 | 81 |
| Randall Middle School | - | $19.0M | 350 | - |
| Millburn High School | - | $14.0M | 138 | 40 |
| Avon Grove School District | - | $43.0M | 50 | 13 |
| St. Bernard's School | - | $1.3M | 15 | - |
| St. Francis Xavier School | 1933 | $12.0M | 50 | - |
| Cleveland Heights-university Heights School District | - | $1.6M | 7 | 26 |
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West Chester Area School District may also be known as or be related to Henderson High School and West Chester Area School District.