The airfield opened in 1928 on 60 acres (24 ha) of farmland purchased by the Kreider-Reisner Aircraft Company. It was purchased by the City of Hagerstown in 1933.

In 1934, after purchase by Fairchild, Kreider-Reisner was renamed the Fairchild Aircraft Corporation. In the following years, an aircraft manufacturing facility was built on the Hagerstown municipal airport site. In the 1940s, the Fairchild Aircraft factory at Hagerstown produced PT-19 trainers and C-82 Packet transport aircraft for the war at the facility, designated Air Force Plant 11. After World War II, Fairchild would go on to produce C-119 and C-123 military transports and license-produce Fokker F27 airliners at Hagerstown. From 1973 to 1984, final assembly and checkout of the A-10 Thunderbolt II was performed at Hagerstown. Following A-10 production, Fairchild shut down the Hagerstown plant. In 57 years of operation, the Fairchild Aircraft factory had built over 10,000 aircraft.

The facility was named Washington County Regional Airport in 1981, when ownership was transferred from the City of Hagerstown to Washington County. In 1998, the county renamed it Hagerstown Regional Airport - Richard A. Henson Field.

Subsidiaries of US Airways Express had served Hagerstown Regional Airport for some time. The airport lost eligibility for Essential Air Service funding on October 1, 2007, because it was located less than 70 miles (110 km) from a larger airport.

The last discontinued destination from Hagerstown by this air carrier group was Pittsburgh International Airport. Due to low ridership and the expired federal subsidy, Air Midwest ended their flights from Hagerstown on September 30, 2007.

Hagerstown Regional Airport was without an airline for just over a year until the advent of Allegiant Air which flew from Hagerstown Regional Airport to Orlando Sanford International Airport with two departures on Friday and two arrivals on Monday. The airline started commercial service on November 14, 2008. The airline used the McDonnell Douglas MD-82/MD-83 aircraft on this route. Scheduled service at Hagerstown ended on July 19, 2010, but service later resumed. On August 13, 2013, Allegiant began another hiatus from operations at Hagerstown Regional Airport. They resumed service on November 15, 2013, with afternoon flights.

Beginning on March 24, 2009, Cape Air served Hagerstown Regional with four flights daily on Cessna 402 aircraft to Baltimore-Washington International Airport in Baltimore. These flights were subsidized by the Essential Air Service federal program. This service ended in 2012 and was replaced on November 5, 2012 with EAS-subsidized service when Sun Air International began offering daily flights to Washington Dulles International Airport in suburban Washington, D.C.

On June 23, 2011 Hagerstown Regional Airport began service from Direct Air, operated by Dynamic Airways, to Lakeland, Florida, and Myrtle Beach, South Carolina. In August 2011, Direct Air decided to temporarily suspend service from Hagerstown, saying that demand for service during the winter was expected to decrease. Direct Air stated they would consider returning to the Hagerstown market in the spring of 2012. Direct Air was subject to Chapter 7 liquidation on April 12, 2012.

Hagerstown Regional Airport's eligibility for Essential Air Service was planned to be cut because the airport had fewer than ten enplanements per service day in 2013, in accordance with the FAA Modernization Act of 2012. United States Senators Ben Cardin and Barbara A. Mikulski and U.S. Congressman John Delaney advocated for the United States Department of Transportation to approve a waiver, pointing to a significant increase in enplanements in early 2014. The Department of Transportation approved the waiver, and Hagerstown Regional Airport retained its eligibility for Essential Air Service.

In February 2015 Allegiant Air began nonstop jet service twice weekly to St. Petersburg/Clearwater International Airport, which was followed by twice weekly service to Orlando Sanford International Airport.

By 2015, Hagerstown Aircraft Services, a maintenance, repair, and overhaul facility at the airport, had closed. A portion of the former Fairchild plant was put up for auction in 2017. After its cancellation due to the owner's bankruptcy, a portion of the plant was sold in August 2019 and the remainder was put up for auction.

In October 2019, the Department of Transportation again announced the end of Essential Air Service to Hagerstown, pending any successful appeals. Southern Airways Express subsequently announced the suspension of ticket sales for their routes from the airport in October 2019.

Given the location near Camp David, Air Force One has landed at Hagerstown Regional Airport on several occasions, but usually the Boeing C-32 aircraft rather than the Boeing VC-25 aircraft.