Many European people lived on the land with the Native Americans before it was open to government land grants; they were called "Squatters". The permanent settlers in Oshtemo came in 1830; Benjamin and Maria Drake appear to be one of the first land owners on Grand Prairie. Mr. Drake once had a successful lumber business on the Delaware River but lost it all in the recession following the war of 1812. He traveled the west for several years and settled near Sandusky, Ohio in 1820 with his wife and two children. Later, the family moved on to live in Newport, Michigan where they raised cattle.
Benjamin Drake arrived in Oshtemo on September 1, 1830; he brought with him his wife, Maria, and four children (Francis, Elizabeth, Jane and Benjamin Jr.) also a herd of forty cattle. Benjamin was 43 years old and Maria was 38 at the time of their arrival in what was to become Oshtemo and Kalamazoo Townships. They found a squatter named Washburn, living on the land in the northwest portion of what is today, Oshtemo's section 13. At first they shared the land, clearing and planting. Mr. Conway also was squatting on the Oshtemo property but Mr. Drake gave him some cash to leave the area without applying for ownership. Many wolves lived in the area. Mr. Drake frequently related the story of one getting into his home and frightening his wife and children. Three Indian villages in the vicinity were the home to about three hundred Potawatomi Indians. They grew and harvested corn and other crops. The corn hills were clearly visible in the prairie land. Indian custom was to use the same hill for several years. Maple sap from the forested area was a treasured commodity not only for the Native Americans but also for the settlers. The Indians used animal paths to travel on as they were the easiest and most direct paths. Soon Indian trails were worn ten to twelve inches deep by migrating tribes. The practice of walking single file had created well defined trails for the early settlers. Many of today's roads and highways use these original paths. The Drakes and the Potawatomi shared the land for some time. Treaties were signed and the Indians were to be transported west by 1840. When the government offered the land for sale, Mr. Drake and Mr. Washburn both began the long trek to White Pigeon, one walking the other on horseback. Mr. Drake was first to arrive at the new land office in White Pigeon to claim 160 acres of the land as his alone. At the time the government was selling land in this area for $1.25 an acre. Most all of Michigan land was purchased from the government for this price. No record has been found of Mr. Washburn since his reported trip through the wilderness. Mr. Drake was attacked by Indians on his trek to White Pigeon, but escaped unharmed. Four others purchased land in the area as soon as the land office was opened: Laban Keyes, Royal Sherwood, Phineas Hunt and Charles Wild. Soon after his claim on section 13, Mr. Drake built a cabin with the help of the local Potawatomi Indians. This was a rudely constructed shelter with a single board for a door. He resided in this structure while building a more proper log cabin and later his permanent dwelling. This was common practice at the time. Unbroken prairies and forest land extended for miles where Mr. Drake settled. The prairies supplied hay for cattle and the trees supplied material for building, heat and cooking as well as the needed maple syrup. Mr. & Mrs. Drake had three more children after moving to Oshtemo: George, Maria and James Fitch. The farm was successful, raising wheat, Indian corn and oats along with some horses, oxen, cattle and milk cows. Sheep were very abundant on the Drake farm; in 1850 there were 420 head of sheep that yielded 1,333 pounds of wool. The Drake family built a lovely Victorian farm house in 1852; barns and other out buildings were added later. The value of the farm and buildings was set at $31,000.
Mr. Drake's land was the site of the first schoolhouse which was built in 1833. Harriet Hubbard was the first teacher. The students were David Keyes, Mary Keyes, Charles Marsh, Benjamin Drake, Frank Drake, Jane Elizabeth Drake, Elizabeth Taft, Eliza Jane Wilmarth, Salinda Smith, and Ebenezer Smith. Many hardships were suffered by the early settlers. It was twenty miles to the closest blacksmith, when a tool broke it meant a long walk for repairs. A successful farmer, Mr. Drake took his first load of wheat sixty miles to market and received forty cents a bushel; his first harvest of corn he traded for a pair of boots. The Drake farm flourished and grew to 480 acres in both townships of Oshtemo and Kalamazoo in Kalamazoo County. He held several offices in the growing community of Oshtemo. Some of the Drake children moved away from the area but Jane and James Fitch lived on the family home as long as they lived. A fire did great damage to the home in 1882 and rebuilding began at once with an added second story to the south and west. Mr. Drake died in 1883 after living to be 96 years old in his historic home at 927 North Drake Road. He remained alert, sensitive and enjoyed speaking of the past until the end of his earthly life. Jane Drake managed the family farm and was caregiver for James Fitch as he was ill. James Fitch died in 1893 at the age of 55 years and Jane continued to raise horses and manage the farm until her death at age 75 in 1899. Some of the Drake family members are buried in Mountain Home cemetery in Kalamazoo