On December 15, 1927 the Territorial Governor signed an Executive Order setting aside an area of 204.8 acres of Territorial land for an airport at Hoolehua, Molokai.

Inter-Island Airways started scheduled operations to Molokai on November 11, 1929.

Between the years of 1927 and 1942, the WPA aided the Territory with funds to gradually enlarge and improve the field which was originally a dirt strip. 

During 1940 14,695 acres were set aside for the use of the Navy. 

The U.S. Army established a radio station on the airport in 1935.  This station was moved to a new location in 1938. 

During 1938 the Territory exchanged with the Hawaiian Homes Commission 27.23 acres of unused land on the west side of the field for 20.78 acres at the southwest corner of the field for an extension to the runway.

Immediately after December 7, 1941 the armed forces assumed control and operation of all Territorial airports.  During this period the U.S. Army made extensive improvements.  Some of the improvements were beneficial to the increased civilian use to come, but others were unnecessary and in some cases even undesirable from a civil aviation standpoint.

Beneficial items consisted of paved runways, taxiways, plane parking areas and lighting of the runway 5-23.  However, extensive repairs were needed to the paved surfaces and to replace the inadequate and obsolete runway lighting system.

Undesirable features included earth revetments and air raid shelters, some of which had to be removed because they were hazards to aviation.

The sewer, water and power systems were hurriedly constructed and were excessive to commercial needs.  Plans were made to construct a modern joint passenger and freight building to meet the needs of the public on Molokai.

By agreement with the U.S. Army, the Territory assumed responsibility for the operation and maintenance of the airport early in 1947.  However, most of the permanent improvements were delayed because title to the property did not revert to the Territory until April 15, 1952.  Some items, critical from a safety standpoint, could not be delayed but expenditures were held to a minimum.

Repairs were made to the existing runway lights, installation of a revolving beacon, obstruction lights, and three flashing hazard beacons on prominent hills in the vicinity of the field.

Location of this field is such that in the past during heavy rains excess mud and water flowed onto the operating area, sometimes necessitating closing the field until an emergency crew was able to clean up.  A system of drainage ditches was designed and completed in September 1953 to alleviate this condition.

Runway resurfacing was performed in 1952 and additionally in 1954.

In 1955, the airport consisted of 288 acres of land, with two paved runways, 5-23, which was 200-feet wide and 4,500-feet long, and runway 17-35, which was 200-feet wide and 3,100 feet long.

Hawaiian Airlines, Ltd. and Trans-Pacific Airlines, Ltd., provided scheduled service to Molokai, and Andrew Fying Service flew on a non-scheduled basis. 

Aeronautical services included paved runways and warm up aprons, paved taxiway and aprons, wind socks, runway lights, lighted wind tee, obstruction lights, flashing hazard beadons, revolving beacon, weather observation station (TPA) and crash and fire protection.