Long before trains cut through the forest, the Northwoods were already drawing adventurous visitors. In the late 1800s—when access still meant paddling, portaging, or snowshoeing—two families opened their doors to fishermen, hunters, and curious travelers. Their efforts laid the groundwork for a tourism boom that would only accelerate once the railroads arrived in 1905.

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At the turn of the 20th century, the forests around today’s WinMan Trails were still mostly untouched. Towering hardwoods stretched for miles, too remote to easily harvest. In the early 1900s, fierce competition between two major rail companies—the Chicago Northwestern and the Milwaukee Road—ignited a boom in the Northwoods.

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The reason WinMan has such incredible trails? It all starts with glaciers. We sit right on the edge of the Winegar Moraine Complex—formed by the last major glacial advance. Those rolling hills and dips in the land? That’s ancient ice shaping the future of exploration.

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The post–World War II era transformed forest use throughout the Northwoods. A booming housing market, rapid industrial expansion, and a growing middle class created unprecedented demand for pulpwood and lumber.

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Indigenous communities hunted, trapped, and traded fur-bearing animals not just for food and clothing, but for tools, shelter, and economic survival. Only after the American Fur Company left the region in 1847 did non-Indigenous trappers begin to participate in meaningful numbers. In the 1890s, Fayette Buck became a premier trapper in the area, running a 75-mile winter trapline that included today’s WinMan Trails. Nearly a century later, Andy Nissala and his nephew Brian Rayala harvested over 200 beavers from the same woods—proof that trapping’s long legacy continues to echo through the snow-covered landscape.

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By the 1930s, Northwoods logging was shifting gears. With most old-growth white pine gone, paper mills and small sawmills stepped in to make use of what remained—pulpwood. The land that’s now home to WinMan Trails played a key role in this transition. Managed by Consolidated Papers, it became a testing ground for sustainable forestry and softwood replanting. At the same time, family-run mills from Robert Loveless and Fred Pukall’s kept the tradition of local lumber alive.

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In the early 1900s, two rival lumber companies—Turtle Lake Lumber from the west and Buswell Lumber from the east—converged on the land that is now home to WinMan Trails. They were drawn here by one of the last great timber stands in Wisconsin. For a brief but intense period, the sound of saws and train whistles echoed across the highlands now traveled by hikers, skiers, and cyclists. Fires in 1910 and 1911 devastated both towns, and only Turtle Lake Lumber managed to recover—operating until 1926. Today, WinMan visitors move through trails layered with the history of these vanished communities and the industry that built them.

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Just northeast of WinMan’s Papoose parking lot and the developing BaseCamp lies a stand of hardwoods that once supported a bustling and vital Ojibwe sugarbush—called Iskigamizigan in Ojibwe. This seasonal maple sugar camp was referenced as early as 1862 by federal land surveyors, who marked the Ojibwe occupied area in their field books as a “sugar camp.” But its roots run much deeper. For generations, this spot was an essential part of the Ojibwe seasonal round, a time when families came together in early spring to tap maple trees and boil sap into maple sugar—a treasured food source, a trade good, and a spiritual gift.

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The glacial hummocks and highlands at WinMan Trails have shaped routes of travel through this region for centuries. South and west of WinMan, the more level terrain of the glacial outwash plains offered easier movement across the landscape—first for Indigenous portagers, and later for wagons, stagecoaches, automobiles, and even railroads.

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Among the many trees in the Northwoods, one stood tallest in the eyes of early lumbermen: the white pine. Today, a small patch of old-growth stumpage just south of the Papoose Trailhead offers a rare glimpse of what these forests looked like before the axe. Thanks to efforts by WinMan and the Manitowish Waters Historical Society—working alongside DNR foresters—this area has been preserved to help tell the story of the white pine era.

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