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Berkshire School Archives: WWII

Landing Page for the Berkshire School Arichives


Berkshire Campus, 1940s

The school almost closed multiple times between the Great Depression and the New Deal era, but the worst period for the school was WWII.  Berkshire only survived the war because a handful of men fought incredible odds to keep it open. They knew the key to Berkshire’s future, and the students’ literal survival, was to become a war machine.

Operation Pied Piper, Berkshire

As for the students, three new boys had just arrived from England as part of Operation Pied Piper to evacuate all children from major cities in the UK. They are the Schofield brothers (John and Allen--12 and 14 years old) and Fredrick Patridge. By March, special military training became required for all students over 17 and for faculty.  They trained three to four hours a week and were divided into two platoons.  There are even guard patrols on campus. 


Trail Yearbook page, 1943

Embracing Roosevelt’s “Arsenal for Democracy,” daily life changes dramatically: students prepare for air raids, and bomb shelters are designated in the Allen Chapel Basement, Infirmary (Senior House) basement, and Berkshire Hall basement. There is a complete campus blackout at night.

Green and Gray,

War Bonds appear in the Green and Gray

Albert Keep, 1942

In June of 1942, after over 40 years of leadership, Mr. and Mrs. Buck retire. Mr. Keep (only 36 and also eligible for the draft) is hand-picked by Mr. Buck as his replacement. Keep graduated from Berkshire in 1924 and, after Princeton, returned as a history teacher and then eventually the assistant headmaster.

Mr. Keep has to solve two problems: pressing money issues and how to prepare the boys for war. Keep finds a solution. First, to make sure boys have their high school diplomas before being drafted, Keep compresses four years of high school into three and accelerates commencement with three graduations a year in January, May, and October. Keep starts for the first and only time in Berkshire school history, summer school.

Ad for Education With Wings program

In 1942,  Mr. Keep and Mr. Vroom of the Lufberry Flying School hatch a plot to have Vroom’s flight school moved to Great Barrington, where neighbors and the town dedicate 20 acres to be developed as Tracy Field. Education with Wings was born. 

Educations with Wings Banner, Memorial Dining Room

1943, the War grinds Berkshire to a halt.

Facing too few teachers and skeletal staffing for maintenance and cleaning, Keep appoints a Temporary Council of 11 boys charged with settling in new boys and taking over afternoon and evening study halls, conducting job assembly, and inspecting fatigues (jobs where students cleaned and helped out).  Also, organized sports end. There was rationing for gas, so no away games, and the rosters were ever-shifting because boys were leaving for war.

Perhaps with these sentiments in mind, Mr. deWindt, the school’s business manager, travels to Washington DC to speed up Berkshire’s direct involvement in the war effort. As soon as he returns,  Headmaster Keep signs contract was with the Army, and 17 Air Corps Cadets arrive at Berkshire between the ages of 17-38.

The cadets are barracked in Spurr House, closed because of a lack of coal for heating. Daily, the cadets rise at 7 am, march to the dining hall for breakfast, travel to the Lufberry Flight School on the rickety school bus, nicknamed Hephzibah;  have flight instruction from 8:00 am to 12:30 pm, followed by afternoon classes and military drilling.

Tracy Airfield

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Navy Cadet, Berkshire fields

They worked was seven days a week, but on Saturdays, they did get the evening off to watch movies in the Berkshire Hall theatre with the students.

Navy Cadets, Spurr House

The cadets and the students are kept separate. 

Trail Yearbook, 1943

Education with Wings leaves the school open because of its service and its slightly more stable financial situation.  Not all schools were as lucky. Avon and Trinity-Pawling closed during the War years.

Del DeWindt became the third Berkshire headmaster.

 DeWindt was one of Berkshire’s first boys and graduated in 1911.  After attending Harvard and Williams, he served in the Navy in WWI. He returned as the school business manager and was uniquely positioned to save the school. deWindt was instantly popular with the boys with all feeling he cared deeply about them.  After just one year as headmaster, the 1944/1945 yearbook was dedicated to him and his wife, Ruth.  The class of 1944C lovingly refers to themselves as “Del’s Boys.”

Education with Wings Expands to include over half of the Berkshire boys

Flying also becomes more accelerated with boys flying solos with fewer required hours of flight time.  And more technical with night flying, solo cross country trips, and flying in formation. They even expand to open cockpit flying for loops, tail-spins, crazy eights, and roll-overs.

Academics changed with “purely cultural classes” being considered frills

There was little Latin, medieval history, music, or arts. Classes that were stressed were English, foreign languages, US History, sciences, and math.  They added: aerodynamics, navigation, meteorology, radio, morse code, auto mechanics, and topography.

Baseball under the Mountain

With interscholastic games canceled because of travel restrictions and gas shortages, intramural competition was even more important.

Baseball under the Mountain

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Trail Yearbook 1943

The Green and Gray teams were renamed “Army and Navy” teams, with games happening twice a week in almost every sport.     

Self Help System

Other interruptions to sports were the military drilling and the work program (Self-Help System (to do for oneself) and fatigues where boys would clean school spaces, mow, answer phones ). By 1944: farming became a large part of the school day.

Women on Campus

Ms. Marjorie Sweet, secretary for Buck, Keep, and deWindt (and many more headmasters afterward), kept the administration running; Mrs. Rennard took over the plays and dramatic club while her husband was overseas. One of the instructors at the Education with Wings was a young woman from Boston.  And the first full-time female teacher is hired. Mrs. Betty Burnes taught English for one year.

Skiing, instrumental to the War effort

While Education with Wings trained hundreds to fly, Berkshire boys were also instrumental in another part of the war effort.  Berkshire, famous for its ski team, contributed significantly to the 10th Mountain Division, a new WWII mountain warfare program that helped turn the tides of the war in Europe. 

Joel Coffin '40

Coffin joined the 10th Mountain Division and trained soldiers to ski. Joel is killed during fierce fighting in Italy in 1945.  He received the Silver Star. His brother Bob, also a skier at Berkshire,  served in the 10th Mountain Division.  The ski trail (built by Mr. Chase after the war) on the mountain is named in his honor.

Post card, 1945

Post card to deWindt

Post card, 1945

Note to Del deWindt from an alum serving in Germany.

Post card front, 1944

Art Chase, 1946

Much to Mr. DeWindt’s relief in 1946,  Art Chase also returns.  He had taught at Berkshire before the war but had been on active duty with the Navy since 1943.

First Aid Class

Art Chase teaching first aid class

Alumni Bulletin

Hundreds of Berkshire boys and teachers served in WWII.

Reunion boooklet

Twenty sons of Berkshire died with the oldest in his 30s and the youngest only seventeen, two years before his own Berkshire graduation. 

Telegram from Jim Geier '44C

By the fall of 1946, enrollment was up to 137, with nine students being veterans, 5 of whom had been at Berkshire before the War.  They received Senior Privileges but could not participate in sports unless their original class had not yet graduated.

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WWII Virtual Event, May 19, 2021

Hosted by School Archivist Bebe Bullock '86, the virtual evening looked at life at Berkshire from 1941 to 1946 and explore how WWII changed Berkshire forever.