The Story of the Oak Leaf Trail: How the First Riders Set Out to Connect Urbanites with Nature, 80 Years Ago

The path of the Oak Leaf Trail was charted 80 years ago with an inaugural ride on Milwaukee County’s vital, winding ribbon of nature.

On a June morning 80 years ago, a group of eight – cycling enthusiasts, officials and a reporter – awoke with a thought not unlike what any number of Milwaukeeans might have today: that it was a pretty nice day for a bike ride. 

They’d ride through the outskirts of the city, and its heart, on a route that Rosie Browne would come to love in the early 2000s, indulging a passion for cycling instilled by her father. They’d bike through the tree-lined paths in Greenfield where today Andy Sikorski enjoys a bit of shade on long, sunny-day rides. They’d take the same bends and turns that Jill Maher would first discover while living in a Downtown apartment building and training for a triathlon.

The eight were about to embark on a 68-mile “test run” of a grand bicycle trail on county park cobblestones, dirt roads and paths, scenic parkways and city streets. They were the first of what would be millions of users of what has evolved into the Oak Leaf Trail, which now spans 125 miles throughout Milwaukee County.

Its nine main lines and connections link with city streets, parks and other bike trails like the Hank Aaron State Trail, the KK River Trail and the Beerline Trail. The north end of the trail connects to the Ozaukee Interurban Trail, which can be ridden all the way to Sheboygan. Links to even more regional trail networks are in development.

The trail was renamed
the 76 in honor of the nation’s bicentinnial in 1976 and became the Oak Leaf in 1996; photo courtesy of Milwaukee County Parks

“The Oak Leaf Trail is all about connection,” says Milwaukee County Parks Director Guy Smith. “It brings a diverse community of trail users together, including cyclists, dog walkers, birders, commuters and runners [and] provides a literal connection between the 19 municipalities in Milwaukee County.”

The vision of its creators, including two in that inaugural group, was to allow Milwaukeeans to return to nature without needing to leave the city. Today, Milwaukee is one of just seven metropolitan areas where more than 90 percent of its residents live within three miles of a public trail, according to Smith. An average of more than 364,000 people used the trail annually between 2015 and 2017. “The Oak Leaf Trail is uniquely Milwaukee,” he says. “Nowhere else in the country has a system quite like it.”

ONE OF THE leaders of the pack that gathered in Lake Park just before daybreak on June 17, 1939, was Harold “Zip” Morgan. Milwaukee’s director of municipal athletics since 1923 was one of the city’s leading cycling enthusiasts, achieving notoriety for his long rides of 50 to 75 miles. The idea for a long-distance trail in the city first came to Morgan in 1936, when the first youth hostelling clubs were formed in the city.

The hostel movement, like many of Milwaukee’s residents, was an import from Germany, where locals and tourists alike were enjoying long hikes along country trails that were dotted with low-cost lodgings. Morgan led hikes along paths and through the southeastern Wisconsin countryside for groups of up to 60. A grand loop that would link Milwaukee to Sheboygan County, with hostels located at 15-mile intervals, was proposed, but only a single area hostel – a farmhouse far out on North Avenue in Wauwatosa – was established.

The hostel movement, both locally and across the nation, was part of the larger effort that emerged from the Roaring ’20s to counter the fantastic technological advances of modern life. The simplicity of an out-of-doors outing was touted as a balm for the weary-minded city dweller and perhaps even a distraction for Americans coming of age in the midst of the nation’s first true sexual revolution.

The back-to-nature tendencies that lingered into the 1930s were given new meaning by the global economic collapse. The Great Depression brought about a boom in the popularity of cycling, which had become a nationwide mania in the late 19th century but had faded in prominence with the emergence of the automobile. The U.S. Census Bureau reported that Americans purchased 640,000 bicycles in 1935, the most in 30 years. But as more Americans turned to bicycles as a means of low-cost transportation, city streets remained clogged with automobiles, trucks and trolleys. Cycling enthusiasts feared that the revival of the sport would be short-lived if there was not some safe alternative for children to biking on sidewalks or in the dangerous city streets.

FROM LAKE PARK, the eight pedaled to Hubbard Park on the banks of the Milwaukee River. Following dirt pathways, they moved north to the Estabrook Parkway, then through Lincoln Park and toward the heart of the northern suburbs.

Their path had been charted by Sam Snead, district commissioner for the Boy Scouts of America, who that morning was on his first bike ride in 35 years. While Zip Morgan had been advocating long-range hostelling routes, it was Snead who dreamed of the ’round-the-city loop. Snead, the Milwaukee Sentinel wrote, felt that “a tour of the parks, which offer all the pleasures of a week in the north country – swimming, fishing, nature study, exercise and resting – would be the answer to a prayer long in the hearts of local parents and progeny.”

The route that Snead had charted for the group followed closely along the lines of the grand “Ring of Parks” that the city had planned for its outer edges. In 1889, the city began purchasing what would become hundreds of acres of fringe land, preserving it before it could be developed and linking these new parklands with winding, tree-lined “parkway” boulevards. Although the ring would never be complete, it offered an excellent framework for Snead’s route.

From Lincoln Park, they followed the river north to Kletzsch and Brown Deer parks. They traversed Highway 100 westward, part of the 10-mile portion of their loop that required main highway travel, then snaked along the Menomonee River Parkway into Wauwatosa. There, the group took a midday meal break at the North Avenue farmhouse hostel.

The Oak Leaf Trail at Whitnall Park; photo courtesy of Milwaukee County Parks

IT WAS NOT until 1965 that the trail was officially recognized by the Milwaukee County Parks Department as a 64-mile road and off-road cycling route. Refinements over the decades had trimmed a few miles from the loop, but the path remained remarkably loyal to what Morgan, Snead and the others had first plotted in 1939. 

By 1967, a 4½-mile paved trail in Lake Park was added to the route with a $35,000 federal grant, the first dedicated length of bike trail commissioned specifically for the project. The Department of the Interior praised the project as a possible national model, and the National Bicycle Institute declared that, with the trail, Milwaukee “may become the bicycle hub of the United States.”

With that initial investment in the trail bringing national attention to the local cycling scene, area officials sought to continue to develop the trail. An area of particular interest was the former Chicago and North Western Railroad right-of-way that ran from Lincoln Park to the former Lake Front Depot site at the foot of Wisconsin Avenue. Once the route of a passenger line that linked Minneapolis with Chicago, the rails had been abandoned in 1961 and the right-of-way had since been acquired by the county.

Ideas for using the corridor were both ambitious and novel – including proposals to use it as an express lane for county buses or a possible pathway for a monorail connecting riverside beer gardens – but in 1974 the county opted to incorporate the path into the bike trail, permitting riders to forgo the off-road routes through the parks and to link directly to Downtown.

The trail cruising through Greenfield; photo courtesy of Milwaukee County Parks

Over the next two years, about a half-million dollars was spent to build a paved path along the old rails and make upgrades to the trail. Miles more of paving reconnected formerly linked parks and parkways, a route that now ran through all but a handful of the municipalities in Milwaukee County. The route was christened the “76 Trail” and marked with red, white and blue signs as a memorial to the national bicentennial and the trail’s supposed length of 76 miles – although at no point was it actually that exact length. 

Use of the trail evolved over the next decade, as it became popular with joggers and portions were used for cross-country skiing in winter. During the late-1970s gas crisis, more people took to the trail for commuter biking as a more economical way of getting around. The paving of the trail was completed in 1978 and one of the most significant expansions of the trail, a 14-mile dedicated trail connecting South Shore Park to the Milwaukee County Grounds via the Kinnickinnic River Parkway, was completed a decade later.

Rechristened as the Oak Leaf Trail in 1996, it then seemed that the next step for the loop would be across the Hoan Bridge. In 1997, a cross-bridge route was proposed, to be paired with a small park at the south end of the crossing. The plan would have streamlined one of the most convoluted segments of the trail and connected the high-traffic sections of the former railroad right-of-way and the scenic lakefront South Shore run. A plan for a temporary cross-bridge trail (which could be removed if traffic disruptions were too great) was approved by federal highway officials. But the Wisconsin Department of Transportation, concerned it might interfere with safe and timely auto travel on the bridge, rejected the plans in 2002 and again in 2011. The Hoan connection remains the only significant proposed addition to the Oak Leaf that has yet to come to fruition.

Charles Whitnall; photo courtesy of Milwaukee County Historical Society

RESTED AND FED, the eight pedaled from the Wauwatosa hostel south to Greenfield Park and rolled along the lush Root River Parkway to Whitnall Park – named for Charles Whitnall, who was then the only commissioner the county park system had known. After an hour inspecting the federal government’s Depression-era “Greenbelt Community” of tidy homes in Greendale, the riders took the rugged trek from the southwestern corner of the county toward the lake. Riding off-road to avoid major streets and highways, the eight connected with the Oak Creek Parkway near South Milwaukee and took the winding path to Grant Park on the shores of Lake Michigan.

By now it was mid-afternoon, and the lazy northeasterly winds had grown harsh, pressing against the weary riders as they pedaled north. They pressed on, through Warnimont, Sheridan and Bay View parks. Through South Shore Park, passing the bathing beaches and intake tunnels and then rolling toward the stinking Inner Harbor, clotted with steam-driven freighters. Crossing the Milwaukee River, they passed Maitland Field – still then a landing spot for seaplanes – and ground on along Lincoln Memorial Drive, past the Lake Front Depot, past the city flushing tunnel, past more beaches and boats. And then, winding around North Point, one last steep grade back up to the scenic greens of Lake Park. They hunkered down for the last leg of their 68-mile journey.

THE RECENT DECADES have seen the trail evolve from something of a hidden favorite of area cyclists to one of the county’s most prized assets. Despite the investments and improvements made as the 76 became the Oak Leaf, there remained lingering worries about safety on the trail. In the early to mid-1990s, “it was a place where people were scared to go,” says Ken Leinbach, a longtime rider of the trail and executive director of the Urban Ecology Center. But, he adds, more recent development along the route has helped to drive a boom in use of the trail and has washed away most worries about safety.

The trail at South Shore Park; photo courtesy of Milwaukee County Parks

The trail was a major factor in selecting the location of the Riverside Urban Ecology Center, which now occupies 15 acres along the trail. “Activating urban green spaces,” Leinbach says, stimulates activity along the trail that heads off potential safety issues and works to introduce people to a part of the city they might have overlooked. The recently opened series of county park beer gardens that sits along the trail serves a similar purpose – an open invitation to the community.

ONE PERSON WHO has long accepted that invitation is Rosie Browne, who both commutes on the Oak Leaf and uses it for recreation. A member of the Cream City Cycle Club since the 1980s, she has made lifelong friends and treasured memories on the trail. Her daily round-trip to work was once 27 miles, but with a path winding through several parks, it proved a wonderful way to begin and end each day.

Jill Maher turned her love for the trail into a book, Milwaukee County’s Oak Leaf Trail: A History, released in April by The History Press. She found a lot of people who felt the same way she did about the trail but also thinks that it remains something of an overlooked gem. “Honestly, I think some of us take the trail for granted and don’t realize what a wonderful free resource we have,” she says.

That resource’s reach is soon to become even greater. In 2016 the Rails-to-Trails Conservancy and Wisconsin Bike Fed launched the Route of the Badger, a 500-mile plan to connect bike routes in southeastern Wisconsin into an expansive regional trail system. It will eventually connect the Oak Leaf to Waukesha, Racine and Washington counties. “As the Route of the Badger is implemented, more neighborhoods that are not currently in proximity to trails would be served directly by new regional trails, and a larger percent of the population would be within a reasonable walking or biking distance of this trail network,” says Joseph Delmagori, senior transportation planner for the Southeastern Wisconsin Regional Planning Commission, a partner in the project.

The trail on the lakefront at Veterans Park; photo courtesy of Milwaukee County Parks

AS THE EIGHT weary travelers pedaled back into Lake Park, with the sun beginning to dip toward the western horizon, they had completed a tidy loop around the nation’s 13th-most-populous city and one of its largest industrial centers – mostly within the calming influence of nature. Coming to rest in the lush green grasses of the park, they reviewed their maps, which they planned to simplify and reproduce for local cyclists free of charge.

Today, the Oak Leaf functions much as it has in the past – as both a practical means of transportation and as a scenic respite for recreation. But at the core of its value to the city is an idea that drove Zip Morgan, Sam Snead and company to ride those 68 miles 80 years ago and that inspired the grand ring of parks at Milwaukee County’s outer edges: that an ideal urban center had a duty to its citizens to balance the conveniences of modernity with a preservation of an area’s natural past.

5 Slices of History on the Oak Leaf

Riding the (Former) Rails

Between Glendale and the lakefront, several miles of the Oak Leaf sit along the former Chicago and North Western Railroad right-of-way. On the northern part of this run, riders cross West Silver Spring Drive, the Milwaukee River and Interstate 43 on repurposed railroad bridges. The Capitol Drive bridge has even been outfitted with an art installation to recreate the passing of the “Twin Cities 400” passenger train which ran this route on its Minneapolis to Chicago run until 1963. A small section of rails can still be found just north of this bridge, hidden in the brush on the east side of the trail.

Bikers along railway; photo courtesy of Alan Magayne-Roshak

New Life for a New Deal Treasure

The former South Shore Bathhouse was renovated and reopened in 2015 as the South Shore Terrace, one of a number of summertime beer gardens that now operate along the trail. The structure was built in 1934 as a Works Progress Administration project to serve the many locals who enjoyed swimming off of South Shore Beach. In 2016, the Terrace began serving food, including a Friday night fish fry.

photo courtesy of Wisconsin Historical Society

The Festival Grounds at Rest

Perhaps no part of the trail is as devoid of nature as the mile or so that fronts the lakefront festival grounds between Discovery World and Erie Street in the Third Ward. And unless the festival park is in use, the stretch is also as vacant of humanity as any other on the trail. It runs through the site of a former airfield and roughly along where the lake’s natural shoreline once would have sat – a stark reminder of how much of Milwaukee’s lakefront is the result of human intervention.

photo courtesy of Alan Magayne-Roshak

Charles Whitnall’s Pride, Joy and Final Resting Place

Another of Charles Whitnall’s contributions to the county parks system is the Boerner Botanical Gardens, found in Whitnall Park in the southwestern corner of the trail. Developed in the 1930s, the gardens contain a magnificent selection of flowers and other plant life maintained by professional horticulturists. The park and the gardens meant so much to Whitnall that, after his death in 1949, his ashes were spread over the park’s grounds.

Milwaukee’s First Airport

Way out on West Capitol Drive, the trail runs through Currie Park, where one of the nation’s first municipal airports went into operation in 1919. Just months after it opened, the Currie Park airfield hosted the first flight of the Lawson L-2 airplane, designed by Englishman Alfred Lawson, who is now credited as the inventor of the commercial aircraft. The airfield would be short-lived, however, and was shuttered in 1926.

“A Grand Old Leaf” appears in the June 2019 issue of Milwaukee Magazine.

Find it on newsstands beginning June 3, or buy a copy at

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