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Ultimate Guide to Bike & Running Trails in Milwaukee (2025 Edition)

Milwaukee isn’t just “Brew City”—it’s a postcard-perfect playground for anyone who’d rather rack up miles than bar tabs – or both 😉 

Whether you’re a sunrise runner chasing that lakefront breeze or a cyclist plotting a caffeine-to-cream-puff century ride, the 414 has trails that slap harder than a Cream City brick. 

We mapped the best bike trails Milwaukee locals swear by (hello, Oak Leaf) and running routes with scenery so good they should charge admission—complete with distances, surfaces, and insider hacks. 

Lace up, clip in, and let’s show Chicago why our lakefront flexes harder.

Why Trust This Guide?

  • Local Data, Freshly Pulled (2025): Mileage, surfaces, and amenities verified against Milwaukee County Parks, Wisconsin DNR, and municipal updates.
  • Locally Reviewed & Endorsed: We’ve vetted this info through countless runs/rides and multiple local sources – including our friends over at Wheel & Sprocket.

1. Oak Leaf Trail – Milwaukee’s 135-Mile Crown Jewel

Fast Facts
  • Segments: 14 color-coded branches (Lake, River, New Berlin, etc.)
  • Elevation: Mostly flat; 2–3 % grades on southern stretches
  • Winter: Priority snow removal within 24 hrs of >3″ snowfall
  • Route: Ride a figure eight around Milwaukee
Why You’ll Love It

This is the arterial network that lets you cycle from the Summerfest gates to suburban beer gardens without touching a four-lane road.

The Lake Line hugs Lake Michigan, the River Line parallels rustic boardwalks, and the Root River segment serves up shaded switchbacks perfect for July heat waves.

Insider Tip (2025 Upgrade): Turn your mileage into bragging rights with the Oak Leaf Discovery Tour Digital Passport—just $5 from The Park People of Milwaukee County. 

Download the mobile “passport,” hit any of the 45+ checkpoints along the 135-mile trail, scan the QR codes as you go, and collect digital stamps for prize drawings (plus a finisher sticker or T-shirt if you splurge on the merch bundle).

Snag yours here: It’s the most satisfying way to gamify your summer long runs and bike centuries. 

2. Lakefront “Lake Line” – Four Miles of Wave-Cooled Speedwork 

Nothing beats the combo of Calatrava skyline, open water breeze, and zero traffic lights. This quick route is technically part of the Oak Leaf Trail (above) but is a noteworthy stretch we had to highlight. 

Markers every quarter-mile help runners pace intervals; cyclists lap from Veterans Park to Lake Park for an effortless 16-mile out-and-back.

Bathrooms & Water: Bradford Beach bathhouse, Lake Park Pavilion.

3. Hank Aaron State Trail – Rail-to-Trail That Links It All

From Lakeshore State Park’s island loop to Wauwatosa’s beer gardens, this 15-mile corridor seamlessly joins downtown employers, American Family Field, and the new Valley Pass protected lane. It’s one of the best EAST-WEST connections our city has to offer. 

Expect crushed-stone west of 44th St; skinny-tires roll fine but drop pressure a notch.

End-of-Ride Beer: Third Space Brewing is 0.2 mi off-trail. You earned it.

4. Beerline / Milwaukee River Greenway – Short, Scenic, Art-Heavy

Clock in your 5 K before lunch. The route swoops under graffiti-bombed trestles and past hidden kayak launches. Combine with the Oak Leaf + Hank Aaron for a figure-eight long run.

And we hear there’s more Beerline coming soon, which will connect the existing trail to the inner city.

5. New Berlin Recreation Trail – Seven Miles of Straight-Line Speed

Beloved by West Allis commuters and speed demons. Minimal shade—bring sunscreen. Connects directly into the Glacial Drumlin at Waukesha for those big-mileage weekends.

6. Ozaukee Interurban Trail – Thirty Miles, Three Charming Towns

Flat, ultra-smooth pavement through Thiensville, Cedarburg (coffee!), Grafton, Port Washington, and Belgium. Train-station museums, lake overlooks, and ice-cream stops break up the distance.

Plus, it connects directly to the Oak Leaf (noted above) so you can ride all the way to Sheboygan – entirely on a protected bike path.

Weekend Hack: Hop the Amtrak Hiawatha to Milwaukee Intermodal, ride Interurban north, Uber back.

7. Lake Country Trail – Kettle-Moraine Roller Coaster

Expect gentle climbs topping 1,100 ft elevation, sweeping lake vistas, and shaded kettle depressions. Water & bathrooms every 4–6 mi at county parks. Ideal half-marathon prep.

8. Glacial Drumlin State Trail (East Segment) – Gravel Epic

Crushed-limestone bliss from Waukesha to Jefferson County. Annual state trail pass required for cyclists. Marathoners favor the Wales trailhead for uninterrupted 10-mile stretches; gravel riders tack on Rome Pond Wildlife Area for bonus scenic miles.

Trail Etiquette & Safety Checklist

  • “On your left!” call out and a quick bell > “Hey!”
  • Lights: Required dusk-till-dawn; 500-ft visibility front / 300-ft rear.
  • E-bike class 1 & 2 allowed everywhere; class 3 prohibited on Hank Aaron west of 76th St.
  • Hydrate: Public fountains May–Oct only. Carry a water bottle November–April.
  • Know your deer: Dawn & dusk sightings are common on Oak Leaf southern spurs—slow up.

Bonus Resources

Run & Ride Clubs:
Bicycling Events
Running Events
Maps & Trail Info

FAQs

Q: What is the longest bike trail in Milwaukee?
 A: The Oak Leaf Trail is Milwaukee County’s longest network at 135 miles, looping and branching through lakefront, riverside, and suburban parkland segments.

Q: Are e-bikes allowed on the Oak Leaf Trail?
 A: Yes—class 1 and class 2 e-bikes are permitted on all paved portions; class 3 speed-pedelecs are restricted.

Q: Do I need a pass for Milwaukee trails?
 A: Only state trails like Glacial Drumlin require a Wisconsin State Trail Pass ($25 annual / $5 day for cyclists 16+). County trails (Oak Leaf, Hank Aaron) are free.

Ready to Roll?

Tag @MilwaukeeUncut with your sweaty selfies and we’ll feature our favorites in the newsletter. Until then: pump tires, charge watches, and own the path.

Upgrade Your Ride

In need of a shiny new bicycle, tune up, or accessories – hit up everyone’s favorite local bike shop, Wheel & Sprocket. Order online, or better yet – get their knowledgeable and friendly staff’s recommendations at one of multiple locations.