In the 1920s, flying was an adventure. For the Whittall brothers of central Massachusetts, the years after World War I were spent testing their skill and luck by flying canvas-covered biplanes over the fields and villages of Worcester County. But the Whittalls, like other local pilots, faced a serious obstacle: there was no airport in Worcester. Farm fields provided a bumpy alternative for recreational flyers, but commercial passenger planes and mail carriers needed the improved runways available at a real airport.

In 1925 an informal group of Worcester businessmen and flying enthusiasts began to scout potential sites for an airport in Worcester County. But, as often happens when committees are involved, the plans stagnated. Finally, Whitin Whittall grew impatient with the delays. He used his own money to hire engineers to survey possible sites. Inches Farm field in North Grafton came up at the top of the list. Whittall took out options to purchase the land, then drummed up excitement and support from Worcester businessmen. Within three weeks, the group had the funds to incorporate, and by October 3, 1927, two runways and two hangers were open for business. Whittall Field became Worcester's first airport.

Whitin Whittal succeeded not only in getting the airport built but also in spreading his excitement about flying. On October 12, 1927, the day the airport was dedicated, roads around the airport were jammed for miles. A huge crowd turned out to witness the opening ceremonies and flight demonstrations, including daring maneuvers performed by a female German pilot. A festival atmosphere prevailed, in spite of endless speeches by politicians and dignitaries.

For 18 years, Whittall Field was one of the busiest spots in Worcester County. Until 1945, the field hosted airplanes such as Jennies, Robins, Wacos, Fords, Stearmans, Cubs, and Taylorcraft; special charters brought visiting performers and dignitaries, and pioneers such as Wiley Post made stopovers on around-the-world flights. In the years leading up to World War II, the field was especially busy with the Civil Pilots Training program.

World War II brought major advances in aircraft design, and it became clear that the old farm fields would soon be too small for modern aircraft. On May 4, 1946, a new Worcester Airport was dedicated near the city's west side; commercial service to New York City began a week later. The old Whittall Field was sold for a housing development in 1951.

The new airport has experienced ups and downs since opening. In the late 1980s, its six airlines served around 350,000 passengers annually. Deregulation of the airline industry created challenges for the nation's smaller regional airports, like Worcester's. The airport's location over 1,000 feet above sea level also means that it is prone to fog and other dangerous weather conditions that cause serious and expensive problems for the airlines. The airport experienced several years without passenger service due to these challenging landing conditions and other factors. In 2010, Massport, which operates Boston's Logan Airport, acquired Worcester Regional Airport.

Daily passenger service to Florida started in 2013 and upgrades to the landing system are due to be in place by the end of 2017. Local and state officials continue to support and invest in the airport and hopes are that their patience will ultimately lead to increased passenger service.