The field was constructed in anticipation of World War II.[6]



In 1951, Air Defense Command arrived, but then turned over the base in 1955 to Strategic Air Command, which sent the 4050th, later 499th Air Refueling Wing, to operate from the base. The 99th Bombardment Wing arrived in 1956. In case of nuclear war, an alternate SAC command bunker, called The Notch, was constructed deep within nearby Bare Mountain.[6]



The 2005 Base Realignment and Closure Commission ruled that Westover would absorb other military units in New England. The expansion proposed the transfer of all military operations at Bradley International Airport to Westover and the nearby Barnes Municipal Airport. The exception to this decision is the 103rd Airlift Wing, which will remain at Bradley. A $32 million building project is underway to accommodate the additional 1600 service members required by the plan.[7]



The new Armed Forces Reserve Center will host Army, Air Force, Marine Corps, and Navy Reserve operations. The Massachusetts Army National Guard will also make its debut at the base.[8]



The base celebrated its 75th anniversary with an air show on May 16–17, 2015, where the Blue Angels headlined the 2015 Great New England Air Show. During this time, it was announced that the Westover was in the running for a squadron of the new KC-46A Pegasus. Later that year, it was announced that the base would not be receiving the plane, which instead was given to the 916th Air Refueling Wing at Seymour Johnson Air Force Base. Westover was also in competition with Tinker Air Force Base and Grissom Air Reserve Base for the plane.[9]



The local government credits Westover with spurring development of the Memorial Drive corridor, including several planned hotels and a high-end retail plaza