Hired as a manager for the Northern Transportation Company in 1878, 24 year old Day managed the sawmill operation near Glen Lake, the docking and wooding operation at Glen Haven and a 1,600 acre farm. By 1880, the wood supply was nearly exhausted. To maintain the area industry, he raised a second growth forest and obtained acres of land to the north and south to cary on a sustained logging operation and farming.
Cut from the same cloth as many ambitious entrepreneurs of the time, Day worked obsessively to acquire wealth through agriculture, land deals and development. One such plan was to rescue the company town of Sleeping Bearville (Glen Haven) by buying the town's land at rock bottom price form the failing Northern Transportation Company he worked for as a young man. He platted the land into streets and lots. The lots were never sold and the town withered with its supporting industry. Undaunted, he continued his personal campaign to develop the region as a tourist playground by selling his second growth forest, Alligator Hill just south of Glen Arbor, to American Park Builders of Chicago in 1922. Day Forest Estates was a "resort deluxe" plan with polo fields, tennis courts, golf courses, a landing strip, marinas and (rumor circulated) plans to build a summer White House for President Calvin Coolidge. Constructing roads through the forest and building pillared entrances to welcome the wealthy estate owners wanting to live in social exclusivity, Day's future looked prosperous, but he died in 1928 and all construction stopped when the depression hit in 1929. The same expectant roads of D.H. Day Forest Estates are the Alligator Hill hiking paths and ski trails today.
On M-22 just north of Pierce Stocking Scenic Drive stands the regional landmark, the D.H. Day Farm. It is privately owned today.