One of Milwaukee County’s biggest trail improvement projects is moving closer to construction — including upgrades to several sections of the Oak Leaf Trail used regularly by North Shore and Milwaukee families.
Milwaukee County Parks is moving ahead with its Oak Leaf Trail Modernization Project, an effort to rebuild aging portions of the trail, improve accessibility and create more consistent wayfinding throughout the system.
After public meetings were held in January 2026, the project has now been divided into two phases. The first group of trail improvements is expected to go out for bids this fall, with construction beginning in spring 2027.
For families who bike the trail, this is worth watching: several of the improvements are along the Milwaukee River Line and Lake Park Loop, two of the easiest sections to reach from the North Shore.
If you’re looking to explore the trail before construction begins, check out our Ultimate Oak Leaf Trail Guide to Milwaukee, which includes family-friendly trailheads, parks, beaches, food stops and an interactive map.
Oak Leaf Trail Modernization Projects
Explore Milwaukee County's planned Oak Leaf Trail improvements. Tap a marker for project timing and details.
Why the Oak Leaf Trail is being rebuilt
The Oak Leaf Trail is much more than a single bike path. Milwaukee County's network now includes more than 135 miles of paved trails, connecting parks, neighborhoods, lakefront destinations and communities throughout the county.
But portions of that network date back decades.
Milwaukee County Parks began building what became the Oak Leaf Trail system in the 1970s. Some of its oldest sections are only about five to eight feet wide, while deteriorating pavement can make them uncomfortable for biking, walking, running or pushing a stroller.
The modernization project is intended to bring those older segments closer to current trail standards.
The work focuses primarily on:
• Widening and repaving substandard trail sections
• Improving ramps and ADA accessibility
• Addressing deteriorating pavement
• Installing more consistent wayfinding signs
• Making the trail more useful for transportation as well as recreation
You can see the latest plans and project documents on the Milwaukee County Parks Oak Leaf Trail Modernization page.
Phase 1: Construction expected in 2027
Milwaukee County Parks currently plans to include four areas in the first construction phase:
Milwaukee River Line through Lincoln and Meaux Parks
This is one of the most locally significant improvements for North Shore families.
The Oak Leaf Trail travels through the Lincoln Park area before continuing north toward communities including Glendale, Whitefish Bay and Shorewood.
Milwaukee River Parkway north of Lincoln Park
Another portion of the Milwaukee River Line extending north from Lincoln Park toward Silver Spring Drive is part of the first phase.
Together, the Lincoln Park and Milwaukee River Parkway improvements should upgrade an important north-south trail connection between Milwaukee and the North Shore.
The area is also receiving additional attention beyond this modernization project. In August 2026, Milwaukee County announced approximately $1 million in federal funding to help replace two Oak Leaf Trail bridges near the eastern end of Lincoln Park, crossing I-43 and Port Washington Road. The bridges date to 1936 and are planned for eventual replacement with structures meeting modern standards.
Lake Park Loop
Another heavily used section scheduled for Phase 1 is the Oak Leaf Trail through Lake Park.
Lake Park provides one of the trail's most scenic stretches, connecting the East Side with Milwaukee's lakefront and destinations farther north.
This section can also be incorporated into a longer family ride connecting Lake Park, the East Side, Shorewood and the North Shore.
Warnimont Park
The South Shore Line through Warnimont Park is also included in Phase 1.
Located along Lake Michigan in Cudahy, Warnimont Park offers another beautiful lakefront stretch of the Oak Leaf Trail and connects with the larger South Shore trail network.
The current Phase 1 timeline
Milwaukee County Parks' latest tentative schedule calls for:
October 7, 2026: Bid opening
November 4, 2026: Bids due
Spring 2027: Construction begins
Fall 2027: Restoration and project completion
That means riders shouldn't expect major construction on these sections immediately this fall. The more noticeable impacts should begin in 2027.
As always, dates can change once bids are received and construction gets underway.
What happened to the other trail sections?
Not every segment included in the original modernization announcement will be rebuilt next year.
Milwaukee County has placed three locations into Phase 2:
• Root River Line between Morgan and Layton avenues
• South Shore Line at Cupertino Park
• Milwaukee River Line ramp near Riverside University High School
Wetland permitting for Phase 2 is currently planned for 2027, with construction anticipated in 2029.
That's a significant change from the early version of the project, which presented all seven locations together.
Another big investment in Milwaukee's trail network
The modernization work is just one part of a much larger period of investment in Milwaukee County's biking and walking network.
In August 2026, Milwaukee County announced nearly $3 million in federal Transportation Alternatives Program funding for pedestrian, bicycle and Oak Leaf Trail improvements.
That includes the approximately $1 million for the two Lincoln Park-area trail bridges, as well as roughly $2 million for pedestrian and bicycle safety improvements at nine locations in communities including Glendale, Bayside and Fox Point.
Those projects complement a growing list of changes happening on North Shore streets themselves. We've rounded many of them up in our guide to how North Shore roads are changing, including projects designed to make walking and biking safer.
Milwaukee County has also been working on a broader Trails Network Plan looking at how existing and future trails can better connect across municipal boundaries.
What this means for families
The Oak Leaf Trail is already one of the North Shore's best free family amenities.
Families can hop onto the system for a short ride through Shorewood or Whitefish Bay, follow the Milwaukee River, head toward Lake Michigan or turn an afternoon ride into a much longer adventure through Milwaukee County.
The modernization project won't radically change what the Oak Leaf Trail is. Instead, it addresses many of the small things that can make a big difference — smoother pavement, wider paths, safer ramps, better accessibility and easier navigation.
And because the improvements around Lincoln Park and the Milwaukee River Line sit directly along a major connection between Milwaukee and the North Shore, those upgrades could be particularly noticeable for local riders.
Before heading out, bookmark our Ultimate Oak Leaf Trail Guide for trailheads, family-friendly stops and an interactive map.
You can also explore more outdoor ideas in our Milwaukee Trails and Trails guides.
And if you're looking for places to combine with a trail outing, check out our Best Playgrounds in Milwaukee and guide to Havenwoods State Forest.
We'll continue watching the Oak Leaf Trail project as Milwaukee County awards the Phase 1 construction contract and releases more specific information about trail closures and detours for 2027.
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