Residents of Olowalu's plantation camps lived a frugal life, many of them growing vegetables, chickens and ducks for home consumption. Fishing was important as both recreation and as a source of food. Everyone knew each other; neighbors shared and took care of those in need.
Sports were important for children and adults alike. Games such as baseball and football played informally at Olowalu supplemented a formal athletic program sponsored by Pioneer Mill. Pioneer Mill supported the athletic programs of both the Alexander House Community Association, a Maui social service agency, and the West Maui Athletic Association. In 1948 there were organized programs in basketball, baseball, softball, jungle-ball, bowling, volleyball, wrestling, and boxing for boys and in volleyball, softball and basketball for girls.
In 1930 a spark from burning cane destroyed the wooden roof of the Olowalu Hawaiian Protestant Church. Members of the congregation continued to hold services where they could. In 1934 the church bought the empty Olowalu School and held services in the teacher's cottage until 1948.
By 1934, M. Ichiki Store, a local chain established in the 1920s in Lahaina, had opened a branch in Olowalu and continued to operate it until at least 1947. The M. Ichiki Store may have taken the business of the C. Sam Lung store, which had ceased to exist. The Kawasakis continued to operate the Olowalu Nihonjin Shokai into the 1940s.
Over time, Olowalu's population and vitality decreased. Company housing was phased out in the 1960s and 1970s, and sugar cultivation ended in the late 1990s.
Olowalu boasts of two sports heroes. Salvador "Dado" Marino, the first world boxing champion from Hawai`i was born in Olowalu in 1915, a member of one of the first Filipino families to work for Olowalu Company. Although he spent only his early childhood at Olowalu, afterward living on the Big Island, Lana`i and O`ahu, he considered Maui his home island. After an accomplished amateur career, Marino turned professional in 1941. After two failed attempts at world championships in 1947 and 1949, he won the world flyweight championship at age 35 in 1950 and successfully defended the title a year later. After a subsequent loss and three unsuccessful attempts to regain the title, he retired from boxing in 1952.
When Marino visited Maui, he was met with crowds of fans who came to watch his exhibition and training matches, to talk to him at the Maui County Fair, and to honor him at banquets and other special events. In 1949, 7,000 Mauians turned out to see him. Because of this enthusiastic reception, Marino and his manager Sad Sam Ichinose considered a change of venue from Honolulu to Maui for his pending world championship bout. In the 1960s he moved to the mainland where he died in 1989.
Olowalu's other hero, Wallace "Wally" Yonamine, was born there in 1925 and raised in the community, living a typical plantation life. A talented multi-sport star at both Lahainaluna and Farrington High Schools, he first turned to professional football. The San Francisco 49ers drafted him in 1947, making Yonamine the first Asian American professional football player.
After a short period of playing minor league baseball on the mainland, in 1951 Yonamine began a four-decade career as a highly successful baseball player, coach and manager in Japan. As a result, he became the first American voted into Japan's baseball Hall of Fame. In 1998 Yonamine received the Japanese Order of the Sacred Treasure for his "extraordinary efforts in promoting the exchange of sports and friendship between Japan and the United States."
When Yonamine was playing ball in Japan, he returned to Olowalu at the end of each season. He still visits, saying "When I go there, it helps me look back over time. Olowalu still makes me feel humble."