From an early age Anna Lindsey rode horses, roped cattle, helped mend fences and set fence posts alongside her father and her brothers on their land in Hawai’i County, Hawai’i. In later years, she would compete in horse races, brand cattle, and bring the beef to market, living the life of a Hawaiian Rancher and cowboy. Born in 1900, she lived until 1995, leaving a legacy of a working ranch and many charitable deeds. Her ranch, titled Anna Ranch, is still active today. Located on the island of Hawaii and consisting of 3.48 acres at the base of the Kohala Mountains. She was a unique woman in the male dominated profession of cattle ranching. She worked on and successfully operated the ranch, bringing innovations and new castle breeds to Hawai’i and making significant contributions to her community. Her legacy and that of her family is being perpetuated, as set out in her trust, with the formation of “the Anna Ranch Heritage Center “in Waimea.
The history of Anna Ranch begins with Anna Leialoha Perry-Fiske’s great grandparents, the Englishman James Fay and Hawaiian native Ka’ipukai, (her full name was Kai’pukai’ikapuokamehameha Kahahana). They wed around 1828, and acquired land where the Anna Ranch house would later sit. The union of James and Ka’ipukai Fey produced one child, a daughter, named Mary Ka’ala Fay in 1830. She wed twice, having 12 children altogether. Her second marriage was to Englishman George Kynaston Lindsey. In 1858, a year before he died, James Fay sold the land where the Ana House is located to his son-in-law George.
As a young girl, Anna was sent away for her formal education. At Sacred Heart’s Academy in Honolulu, there she met Queen Lili’uokalani, the last reigning monarch of the Hawaiian Islands whose kingdom had been deposed in a coup in 1893. When the Queen died in 1917, Anna was asked to sing in the choir for the Queen’s funeral. At the age of 19, Anna married Henry Lai Hipp of Hilo, who later in 1935 won a seat in the Territorial House of Representatives. During her 25 year marriage to Henry Lai Hipp in Hilo, Anna was particularly active in community beautification projects. She served as a park commissioner for Hawai’i County from 1933-1939 and was an active member of the Hilo Women’s Outdoor Circle where she served as its chairwoman for eight years. Two significant projects Anna took part in were the tree-planting project along Banyan Drive in Hilo and the beautification of the Akaka Falls area. Anna would visit her family and help with brandings and ranching activities. She also kept up with her equestrian activities, charging a dollar per hour for riding lessons. Through the 1920s and 1930s, Anna trained her own race horses and was one of the few female jockeys in Hawai’i at that time. She won many races and the horses she trained often took top honors.
In 1939 while her father was ailing, Anna separated from Henry Lai Hipp to return home to care for her parents. Her father died that year and Anna divorced Henry and took over the running of the ranch. When Anna took over the running of the ranch she had no idea that during her father’s long illness the ranch was on the verge of bankruptcy. Mary Rose Lindsay died in 1940 leaving Anna in complete charge of the ranch. Through the sale of properties she owned in Hilo, some smart investments, and by doing most of the ranch work herself, she was able to save the ranch and pay off a loan in the allotted time.
In 1941, the year after her mother died, Anna changed the name of the ranch from Lindsey ranch to Anna ranch. Anna Lindsey truly was a “cowboy” as she worked six days a week riding the range, mending fences, branding cattle, and buying stock from nearby ranches. She only occasionally hired other cowboys when she needed help with branding or moving cattle. During World War II, Anna was one of the first women in Hawai’i to get her butcher’s license. She selected the cattle to be slaughtered and when she felt the local butcher was charging too much, she slaughtered her own beef, driving the carcasses to the Hilo Meat Market, which in those days was a five hour trip each way. During World War II, many service men were stationed in Waimea. In 1945, Anna wrote the central Pacific Base Command complaining of the marines damaging the stone wall cattle pens, which led to her cattle running loose. She did entertain officers and nurses from Camp Tarawa at the ranch during the Second World War. In 1943 Anna Lindsey married James Lyman Perry-Fiske, also part Hawaiian, and also a keen horseman who loved the outdoors. Anna earned an award in 1975 from the Association of Hawaiian Civic Clubs. She raised more money for the American Heart Association than any other individual in the United States for several years, using the pageants “Old Hawai’i on Horseback’ that ran from 1964-1983. She received three distinguished service medallions from the American Heart Association, the highest award accorded to a volunteer. In 1979, Congressman Daniel Akaka honored Anna on the floor of Congress for her fundraising efforts. Anna was also on the Board of Governors for Hawai’i Preparatory Academy since its inception in 1945 and continued to serve on its board until a few years prior to her 1995 death. She also supported Easter seals and donated her own money to help build an emergency room at the Lucy Heniriques Center in Waimea.
The major buildings on the property, including the ranch house, the slaughter house, the barn and the garage were constructed between 1910 and 1930 The buildings are vernacular in style, and are rectangular or modified rectangular with gable roofs made of corrugated-metal, painted white. There are some design aspects of the buildings that respond to the Hawaiian climate, such as elevated floors above ground level, exterior porches, screened-in porches and installation of windows and screens. The ranch house is a wood-frame, single-wall structure comprised of additions and alterations that were completed by 1930. With a foundation of lava rock and Douglas Fir wood, the ranch-house is a one-and-a-half- story bungalow with a modified, rectangular plan and four major intersecting gable roofs and adjacent shed roofs. The Anna Ranch was listed in the National Register of Historic Places on April 28, 2008.
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