Greenwood was a small hamlet south of the Dominion Atlantic Railway’s Kingston Station. In 1942, the Royal Air Force established RAF Station Greenwood and built an aerodrome on nearby farmland to provide a facility for training aircrew under the British Commonwealth Air Training Plan. The Royal Canadian Air Force took over the facility in 1944, renaming it RCAF Station Greenwood, a name it maintained until the 1 February 1968 unification of the Canadian Forces which saw the airfield and associated facilities renamed CFB Greenwood. In July 1997 the air base became one of eleven operational wings in Canada, and was designated as 14 Wing Greenwood.

During the 1970s–2000s, the village of Greenwood expanded in population as numerous other air force bases in eastern Canada closed and their aircraft and personnel consolidated at CFB Greenwood. Much of the housing in the heart of Greenwood is for the military families stationed at the base, and are referred to as PMQs. Most of the non-military housing for the village is located on the outskirts.

Today, the village and airfield’s combined population numbers approximately 5,400. The village hosts numerous services and is also the location of the Greenwood Mall, the largest shopping mall in the Annapolis Valley. In 2015 it was renovated to accommodate a new department store, which has reinvigorated the shopping centre.

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