Early Toll Roads of Wisconsin

Before it became a full-fledged state, and before railroads and highways, people in Wisconsin got around by a network of rutted pathways carved into the curving landscape. In mid-1800s, roads assembled from local timber provided a suitable, though imperfect, alternative for moving people and goods across the wilderness.

The earliest roads in Wisconsin were first trod by moccasins and hooves. Many routes traced along rivers and streams. They transported mail, goods and supplies but with a fair amount of difficulty. A man on foot could manage a terrain that was, at times, steep or heavily wooded, and he could make his way around fallen trees or craggy outcroppings. At the reins of a wagon, those same maneuvers were extremely difficult.

The rough conditions of those early pathways were exacerbated with the coming of the wet weather each spring, as the previously hard ruts turned into slosh. Freighters’ wagons sank in the mire. Many a teamster would rail against the powers that be, shaking his fist toward the sky, turning blue as epitaphs spewed from his lips. One circuit judge regularly had to abandon his carriage, wheels deep in mud, and foot it to the nearest farmhouse – most likely uttering a few profanities of his own on the way.

The condition of roads in Wisconsin mirrored the rest of the country. Communities throughout the United States were all in the same rut. Addressing conditions, one was heard to say, “The roads are impassable, hardly jackassable.”

Early Wisconsin, carved from the Old Northwest Territory, was unchartered wilderness. In May 1832, mail carrier James Halpin had no choice but to make the overland portion of the route from Prairie du Chien to Fort Snelling on foot. The delivery of the mail was paramount in the minds of the early settlers. Mail was the connection between pioneers and family back home. Goods and money also were sent via the mail – and sometimes it made the difference between surviving a tough winter or not. After the establishment in 1834 of the first mail delivery route from Green Bay to Chicago, a small newspaper ran the following refrain in each issue:

“Three times a week, without any fail
At four o’clock we look for the mail
Brought with dispatch on an Indian trail.”

The growing movement of goods and people through Wisconsin necessitated a better means of travel. The solution: a road built from wooden planks, a material in plentiful supply. Though it wasn’t a perfect solution, it did set an example for the transportation of the future.

This diagram of a plank road shows how wooden planks sandwiched between curbs and supports created a thoroughfare for carts and horses. (Wikipedia photo)

A Reliable Route

August A. Bird was one of the Wisconsin Territory’s commissioners entrusted with erecting public buildings in the newly ordained capital. He left Milwaukee en route for Madison on May 31, 1837. It soon became clear that, before building the new capitol, a crude road would have to be hewn from the forest to allow wagons filled with tools and supplies to make their way to Madison.

August A. Bird was charged with building up Wisconsin’s capitol city. (Geni.com photo)

Fallen trees, hills, ravines and marshes awaited them, and the un-bridged streams, as well as the Rock and Crawfish rivers, had to be maneuvered. By the time Bird and his group of 40 workmen arrived in Madison, the “task” he was entrusted with must have seemed more like the “task” he was “saddled” with. This was the reality of Wisconsin’s overland transportation system in those days.

Citizens argued for improved roadways, as those in existence were “incommodious,” they said. With each territorial legislative session, roads were commissioned to be laid out at the expense of the counties through which they ran. But that was the extent of it: laid-out only. Counties were responsible for constructing the roadway through their domain. Local residents had the choice of taking up pick and shovel or paying the cost of construction. This did not materialize.

As Wisconsin developed and bourgeoned into statehood, petitions for new roads multiplied. Settlers recognized early on the importance of having good roads. In a town meeting in Sheboygan County, when it was proposed to raise $100 for roads and $1,000 for schools, voters reversed the sums and gave $1,000 to road construction.

The notion of building turnpike and plank toll roads through Wisconsin appeared in the late 1830s. The government did not have the financial wherewithal or the legal standing to assume responsibility for road construction. Private enterprise was the remedy.

Plank roads easily gained popularity. They were an improvement over deteriorating dirt roads. To alleviate the muddy conditions along a route, 3-inch-thick oak planks were laid atop wood braces, making a noisy but smoother base for hooves and wagon wheels to move along.

The legislature enacted several bills authorizing charters and dictating turnpike companies to construct those badly needed roadways. Their success rested upon the assumption that the tolls collected would pay the private companies to construct and maintain them.

The Lisbon and Milwaukee Plank Road Co. was ordered to capitalize $50,000 by the territorial legislature. As wood was abundant, the new thoroughfare was to be constructed of timber and plank, “so that the same forms a hard, smooth and even surface” from Milwaukee to Watertown.

Wisconsin did not have as large a population as states to the east. Efforts stalled; $50,000 was hardto come by. Die-hards pushed forward, holding a “Plank Road Ball.” The celebration helped raise funds.

The strongest incentive for the roads was the weather. As spring sprung, it was accompanied by heavy rains. There was nothing better than rutted, impassable mire to boost subscriptions of turnpike company stock. The capital of $50,000 was eventually realized. The Plank Road Company’s charter was amended to include other routes, and then more money was needed. The firm had taken on another name: the Madison, Watertown and Milwaukee Plank Road Co.

Once again, subscriptions lagged, not from lack of interest but from lack of hard currency. A new tactic was employed: area farmers were offered small stock subscriptions, which were paid for in labor and materials. It was a fair trade: the farmer’s timber and the sweat from his brow for the new toll road that afforded him increased markets.

Other turnpikes followed, charters were awarded, stock was proffered to obtain funds to complete and maintain those new toll roads.

The strategy was not without pitfalls. The topography, severe in some cases, caused a departure from the proposed route. Those who might gain financially from a new thoroughfare would lobby hard for the route. Lack of a labor force could be a problem. When crops were ready for harvest, workers were in the fields and unavailable to work on the roads.

Commerce Flows

As the number of new toll roads increased, so followed commerce. Business increased and more goods were hauled over the roads, thus feeding the continuing need for more routes.

During this heightened time of business travel, the roads hummed with traffic. In Milwaukee, commercial exchange coming into the burg increased dramatically. The Milwaukee Sentinel and Gazette tabulated that, during a three-day span, wagons hauled 15,000 bushels of wheat over the new Watertown Plank Road into the city. They also noted increased loads of barley, produce and furs. Outgoing traffic was double the incoming rate.

Edwin Bottomley bought land on the Racine and Burlington Road. (Library of Congress photo)

Freighters were not the only beneficiaries. Stage line fares increased threefold.

In 1850, toll rates were determined by the mode of conveyance. A wagon, cart or sleigh drawn by one beast was obligated to pay one cent per mile. Drawn by two, the toll usually doubled. Those driving or leading cattle, sheep, hogs or other beasts were also responsible for a specific “fee per score of animals” to be paid at the toll gate.

There was a toll gate every 5 miles. One traveler noted: “at the toll-gates their keepers were usually busily engaged in taking the toll, for sometimes three or four conveyances stood in waiting.”

Some travelers were averse to paying the toll and used any slick way possible to avoid paying them. A number of locals would detour around the toll gates, creating their own “shun” pikes. A commuter would exit the pike and then return to the road after circumventing the tollgate. The more brazen would wait until the toll taker was otherwise occupied and scoot by unnoticed.

In some cases, local residents feared they might be priced out by the cost of traveling for events such as church services; farmers feared being charged each time they moved livestock from one pasture to another. Oftentimes, to alleviate those fears, some actions were exempt from paying tolls.

The tolls collected on the thoroughfare paid handsome dividends to investors. During its height of travel in and out of Milwaukee, $600 a week was drawn from tolls. A 7% per annum was paid. Annual earnings reached a whopping 25%.

The premise that investors would realize dividends from the tolls was not the only attraction. Those with an eye to the future did not look to profit directly from the turnpike’s proceeds, but for more indirect reasons. Some saw the turnpikes as avenues that would increase commerce and open new markets. A number held title on property adjacent to the proposed routes. They pinned their hopes on the expectation of new businesses becoming established and settlers putting down roots along those thoroughfares.

Edwin Bottomley, a transplant from England, recognized the attraction of new roads. Adopting Wisconsin as his home, he purchased land along the Racine and Burlington Road. Expanding this route provided a smooth track from the interior to the lake shore.

In July 1848, in a letter home to his father in England, Bottomley made note: “The neighborhood is likely to be advanced in value considerably owing to the plank road coming through the settlement.”

As more turnpike companies fulfilled their projects, networks emerged. In 1851, the Sheboygan and Fond du Lac Plank Road Co. was chartered. This was followed by Sheboygan and Calumet Plank Road. Completed in 1854, it extended to Howards Grove. The starting-off point for the Sheboygan River Plank Road was at Sheboygan Falls. These turnpikes helped Sheboygan earn its name of the “Chair City” by opening avenues for thousands of manufactured chairs to be exported.

By the late 1850s, quite a number of plank road companies were chartered. In areas where supplies of lumber were available, these were a feasible choice.

These new, more accessible turnpikes were not welcomed by all who depended on commercial pursuits. The new, wider roads allowed for more wagon trade. This drew business away from those who used pack-animal trains to haul goods; wagons could carry more freight and travelled faster than those leading pack animals, single file, along a narrow trail. This created bad blood between the pack-horse drivers and the wagon freighters, resulting in fists flying when they came face-to-face. And with the demise of the rutted roadway, many a blacksmith was left with idle time as fewer repairs were needed.


The storied narrative of the toll road system in Wisconsin is a barometer measuring its growth and geographical expansion. The toll road companies fueled the state’s bourgeoning economy.

There were hundreds of charters issued, but not all resulted in completed toll roads. Common issues, including lack of investors or an inadequate labor force, added to the failure rate. Severe topography, swampy conditions, impassable rocky crags and heavily wooded areas could double or triple the already formidable construction costs that normally averaged $2,000 per mile. Those extreme physical factors could put a project financially out of reach.

Constructing turnpikes was one thing. Maintaining and repairing them was another. Washouts were common; stumps previously hidden below grade suddenly appeared, and at times rocky surfaces were too rough.

There were other drawbacks. One was the lifespan of the planks. They would fail due to the heavy loads put upon them or begin to show signs of rot. Within a few years, the boards would have to be repaired or replaced.

Also problematic were the plank roads in areas prone to flooding. In high water, planks would float away.

They were secured by pounding with a heavy maul until they rested firmly on a set of stringers. Nails were not used, as they could work loose and be driven into an animal’s hoof. That same high water would wash out the dirt foundation below the stringers, leaving gaps under the planks.

Wagons, heavily laden with lead from the Mineral Point district enroute to Milwaukee, would break through the wooden members, leaving gaping holes in the road. For a quick fix, small bits of lumber, brush, and sand or soil were crammed in, filling the gap. This was a danger to man and beast.

Needed repairs began to overwhelm the toll road companies. Conditions were similar in neighboring states. On some routes, planks were not the only option. Of the 38 miles completed on the old Madison Road, some sections were planked, while others were well graveled.

The attraction to plank roads was further reduced by the arrival of the railroads. Trains reached Watertown in 1855, and within eight years the toll road was described as being in “wretched condition.”

“It was broken and dilapidated and dangerous to drive over,” wrote one traveler.

No longer teeming with commerce, the toll roads tapered off – as did maintenance. In 1887, control of the road was transferred to public ownership. Other toll roads experienced the same fate.
Some areas still relied on the toll system.

In 1872, the Lake Avenue Turnpike constructed a toll road in Whitefish Bay, following a route along the lake shore. One of the last toll roads in operation was the White Fish Bay Road. It ceased collecting tolls in 1913.

A number of toll roads found life as feeder routes, according access to bridges spanning rivers and large streams. Routes would link communities with rivers such as the Sheboygan, Menominee and the Milwaukee, as well as the Fox and Wisconsin. These legacy routes allowed access between Lake Michigan and the Mississippi River.

As the railroads replaced toll roads, a number of these old plank roads remained as valuable connector routes to and from the rail lines.


Wisconsin’s toll road system established a network of arteries connecting the entire state, fueling the economy, and allowing supplies and materials to flow from one end to the other. Those roads allowed people, staples and commodities from Milwaukee and other economic centers to reach the hinterlands, thus developing new communities. At the same time, the turnpikes created gateways for produce from the western interior of the state to reach the more urban eastern part.

(Wikimedia Commons photo)

Some vestiges of those roads, laid out in the first half of the 19th century, are with us today. A portion of the old Milwaukee-Watertown wagon road, which later became a plank road, makes up part of what is often called Highway 16. It was locally known as Oconomowoc Road. The Janesville Road, sometimes known as the Milwaukee-Janesville Plank Road, dates to 1849, and it was for many years a major route for the transport of agricultural products to Milwaukee. Now a major divided highway, this roadway no longer carries a reference to its origins.

Until December 1999, the old toll house at the end point of the old Watertown Plank Road stood on what is today East Gate Drive. With little fanfare, other than a two-edition article running in the Watertown Daily Times, this historic remnant was demolished after nearly 150 years of watching over the road. It was a page in Wisconsin’s early transportation history lost to time.

• Turnpikes and Toll Roads in Nineteenth-Century America, by Daniel B. Klein, Santa Clara University and John Majewski, University of California-Santa Barbara
• Demolition of Old Toll House, Watertown Daily Times, Dec. 4 & 11, 1999.
• Tabulation for three days of imports into City of Milwaukee, Oct. 31, Nov. 1 & 2, 1849. Milwaukee Sentinel and Gazette, Nov. 8, 1849.
• An English Settler in Pioneer Wisconsin: The Letters of Edwin Bottomley, by Edwin Bottomley, 1918. State Historical Society of Wisconsin.
• Early American Technology: Making and Doing Things from the Colonial Era to 1850, edited by Judith A. McGaw, 1994.
• From the History of Wisconsin: In Three Parts, History, Documentary and Descriptive, Part II, Vol. 3, by William Randolph Smith, 1854.
• History of the Territory of Wisconsin from 1836-1848, by Moses McCure Strong, 1885.
• Stories of the Badger State, by Reuben Gold Thwaites, 1900.
• Territorial Legislation in Wisconsin, annual address before the State Historical Society of Wisconsin, by Hon. Moses M. Strong, Feb. 4, 1870.
• The Story of Wisconsin, by Reuben Gold Thwaites, 1890.
• Waymarking.com, Plank road historic markers.
• Wisconsin in Three Centuries, 1643-1905, Vol. 4, by Henry Colin Campbell, 1906.
• Wisconsin: Its Geography and Topography, History, Geology and Mineralogy; Together with Brief Sketches of its Antiquities, Natural History, Soil, Production, Population and Government, by I.A. Lapham, 1846.
• Wisconsin: Its Story and Biography 1848-1913, Vol. II, by Ellis Baker Usher, 1914.