North and South Manitou Islands were occupied by Native Americans at least by 1,000 B.C.E. and possibly as early as 11,000 to 8,000 B.C.E. North Manitou Island is one of the richest sources of archaeological discovery in the Lakeshore, especially along the bluffs on the north end of the island. Both islands have significant sites from the late Woodland Period (600 B.C.E. to 1620 C.E.), the most pronounced period of occupation and activity in the area's history.
Logging was a major factor in the history of the island, which like South Manitou Island, was a strategically located source of wood for early steam ships traveling the Great Lakes. Much of the early history centers on wood dealer Nicholas Pickard, a New Yorker who came to the island in the 1844-1846 period and by 1857 evolved into the biggest landowner on North Manitou. He built wooding docks at various locations, including on the west side where the town of Crescent developed.
According to Simon Pickard, brother of Nicholas Pickard, there was an Ottawa Village numbering 300 where Leland is now. The residents of the village used birchbark canoes to visit the island to fish and buy goods. There was no other place to trade nearer than Mackinac Island. In 1844, Frenchman, Nazaros Dona was a trapper who lived near the Ottawa village, but he later moved to North Manitou Island and engaged in fishing. Great quantities of white fish and trout were dried or salted and shipped in barrels to the mainland markets. Dona's Point is named after him. The name is misspelled on many maps and appears as Donner's Point.
Other woodcutters were on the island earlier, but not for sustained settlement. Joseph Oliver, a native of Pennsylvania credited with being the first settler in Benzie County, was described in one 1892 account as having "removed to Manitou Island" in 1820 for trapping and fishing.
North Manitou's earliest recorded landowner, Neil McFadyen of Erie County, Pennsylvania bought about 45 acres in 1848. The first real land mogul was Albert W. Bacon of Grand Traverse County, who during the 1860's acquired 6,765.9 acres for later resale.
Cornelius Jones built a sawmill on the east side of the island which he operated until 1855. In 1856, a second sawmill was built for Edwin Munger in the village, then knokwn as Aylsworth and later Crescent. John Dalton came to the island in 1848 and was employed as the manager of one of Pickard's docks. A year later, Moses Dexter settled his family on the island. He was a blacksmith. The wooding station and sawmills were dependent on large numbers of horses and oxen to haul heavy loads.
By 1860, the island had become a small "melting pot" of immigrants. The population was 269 with the majority being foreign born, recent arrivals from Norway, Germany, Sweden, Poland, Ireland, Denmark, Canada, France, and England. There were 56 households in 1860. During this period, the island was a way station, where passengers bound for mainland ports were often put ashore with all their worldly goods to await transfer to another boat to their port of destination.
These early settlers began clearing land and planting their principal crops of potatoes and cabbage while continuing to work as woodchoppers. The population of the island fluctuated widely depending on the season and the economic activity at the moment (wooding, logging, farming, and development as a summer resort).
The first school, a log structure erected in 1895, could seat 36 students. The new school was built in 1907 and faced Lake Michigan on a one acre tract. It was a wood frame building with a porch extending across the front. There was a well and hand pump near the porch and in the early days, two outhouses. It was remodeled in 1929. A second school was located in the village of Crescent between 1909-1917.
Much of the early story of North Manitou is the story of big landowners. It was almost always owned by one or just a few large landowners. Roger Sherman and George McConnell held title to large tracts of island property in the early 1920's and became the basis for establishing the Manitou Island Syndicate, the forerunner of the Manitou Island Association. By 1925, plans were underway to develop the island as a sportsman's hunting preserve. In 1926, William R. Angell, under the aegis of the Detroit Trust Company, bought up much of the island.
There is no indication that deer were present on the island prior to 1925, when the Manitou Island Association purchased nine adult deer - four bucks and five doe to begin the deer herd. The deer thrived and rapidly multiplied and were allowed to roam across the entire island. The forest began to have the groomed appearance of a city park as a result of the deer feeding on ground cover and low-hanging branches. They seemed to favor maple and juniper, but eventually browsed on everything except beech, which continues to spread across the island.