Early years

Worcester's entry into the world of aviation began in 1925, when city officials commissioned a study to examine sites for the city's first airport. On the list of sites was land owned by a wealthy local citizen, Whitin Whitall. In 1927, Whitall, independently of the city commission, set up an airport on his land in North Grafton, 500 feet (150 m) above sea level. This two-runway airport opened for leisure travel on October 12, 1927.

As air travel became more popular, airport expansion was the subject of a second study commissioned by the city. The Grafton airport was deemed too small to accommodate the air travel needs of the region. The location of the present airport, Tatnuck Hill, on the borders of Worcester, Leicester, and Paxton, was high on the commission's list. One problem noted by the commission was the weather: at 1,000-foot (300 m) above sea level, the Tatnuck site was often surrounded by fog. Despite this problem, the city eventually chose Tatnuck as the new site, and construction began in 1944. The airport was ceremoniously opened on May 4, 1946, and started regular passenger service one week later on May 10, 1946. That same year, Northeast Airlines was operating nonstop Douglas DC-3 service to New York Newark Airport, Boston and Lawrence, MA as well as direct one stop DC-3 service to Portland, ME. The Grafton airport remained in operation until 1951, when the owners, due to the dwindling traffic, decided to dismantle the airport. The land was redeveloped as a residential neighborhood. Leicester Airport, a small private airfield also built during the first half-century of aviation, was active until the 1970s. It still sits, now mostly overgrown in the shadow of Worcester Regional which in 1969 was served by Northeast Airlines with McDonnell Douglas DC-9-30 jet and Fairchild Hiller FH-227 turboprop flights nonstop to New York LaGuardia Airport as well as to nearby Boston and Manchester, NH.

Northeast Airlines was then acquired by and merged into Delta Air Lines which in 1973 was continuing to serve Worcester with McDonnell Douglas DC-9-30 jet service nonstop to New York LaGuardia Airport and Manchester, NH as well as direct, no change of plane DC-9 jet service to Atlanta, Boston and New Orleans. By late 1979, Delta was operating all of its flights into Worcester with Boeing 727-200 jetliners with nonstop flights to New York LaGuardia and Manchester in addition to direct, no change of plane 727 jet service to Boston, Houston, Jacksonville, FL, Orlando and Miami. However, Delta was no longer serving the airport by the early 1980s. In 1981, two commuter airlines were serving Worcester: Bar Harbor Airlines operating Convair 600 and Beechcraft 99 turboprop aircraft with nonstop service from New York LaGuardia, Hartford and Manchester, and Precision Airlines operating shuttle service into the airport with thirteen nonstop flights operated every weekday from Boston Logan International Airport (BOS) flown with small Piper Navajo twin engine piston aircraft.

Millions of dollars were spent replacing the old terminal, which hosted a half-dozen airlines before its demolition. In the mid-1980s and early 1990s, major carriers, such as Piedmont, Northwest Airlines, Continental, and USAir all flew mainline jets into Worcester. In addition, smaller carriers, like New York Air and Presidential Airways also had jet service. The small terminal had two ground level jetways built to accommodate the growth. One by one, those carriers left.

2000–2020

In 2001, Pan American Airways (1998–2004) was operating daily nonstop Boeing 727-200 service to Orlando, Florida via the Orlando Sanford International Airport (SFB).

Allegiant Air commenced commercial service to ORH with flights to Orlando/Sanford, Florida (SFB) on December 22, 2005, and expanded to four flights per week in March 2006. Allegiant announced on August 22, 2006, that they would cut ties with the airport, citing high fuel costs and passenger loads in the 80% range as the reason for departure. The announcement of flights ending took people by surprise as service was popular and well-regarded by the flying public throughout Allegiant's entire tenure at the airport.

On September 4, 2008, Direct Air announced they would begin service to Worcester beginning in November 2008, with flights from Orlando/Sanford, Florida and Fort Myers/Punta Gorda, Florida. The flights were originally operated by Virgin America using Airbus A320 aircraft. However, Direct Air was required to return the aircraft in June 2009 to suffice Virgin's rapidly expanding domestic routes. At this point, Direct Air began operating flights using Boeing 737-400s owned by Xtra Airways. Due to this being a wet-lease agreement, there were times where the aircraft was unavailable and other aircraft had to be chartered for the flights. Such examples include service with Airbus A320 from USA 3000 and Boeing 757 from North American Airlines. In March 2009, Direct Air added additional flights to Myrtle Beach, SC. In July 2010, Direct Air expanded their Worcester service further to West Palm Beach, Florida.