C. C. McCarty, brother-in-law of John E. Fisher, founder of Glen Arbor built a sawmill and an inn on the beach west of Glen Arbor in 1857. He called the settlement Sleeping Bearville and the inn was named Sleeping Bear House. McCarty built a dock at Glen Haven in 1865. The location of the dock in Sleeping Bear Bay offered a more protected harbor than some of the other docks in the area. McCarty also built a sawmill on Little Glen Lake where they used tugs to move logs from various parts of the lake to the sawmill and once the lumber was cut up, it was transferred to the Glen Haven dock by wagon or sled. By 1870, a tramway more than two miles long was built.
Glen Haven's development was slowed when many of the settlers left to fight in the Civil War, but accelerated again through the Homestead Act of 1862. P. P. Smith, a returning Union soldier became foreman for Northern Transit Company (NTC) at the Glen Haven cord wood station and later became Glen Haven postmaster.
In 1878, NTC President Philo Chamberlain acquired Glen Haven in order to assure a reliable supply of wood for a 24-vessel fleet providing service between Ogdensburg, NY and Chicago or Milwaukee. To serve as NTC's agent in Glen Haven, Chamberlain picked D. H. Day, his sister-in-law's younger brother. Before long, Day had bought most of NTC's properties including the village of Glen Haven. He also bought shares of two NTC steamers (Lawrence and Champlain).