Sugar cultivation in Makawao began in 1857 with the East Maui Sugar Plantation also known as the Kaluanui Plantation. The most significant Makawao sugar operation began in 1869, when Henry P. Baldwin and Samuel T. Alexander purchased a 12-acre Hawaiian homestead and the 559-acre Bush Ranch in Sunnyside. These two parcels grew into the giant Alexander & Baldwin Corporation.
Pineapple started in the Makawao area after the turn of the 20th century at a number of ranches and small properties. In 1926 Libby, McNeill & Libby began planting in Makawao along with the newly established pineapple division of Haleakalā Ranch and Maui Agricultural Company. The two companies merged to form Maui Pineapple Company. The pineapple workers lived in the town itself and in outlying areas. Makawao town served as both the commercial and social center for workers.