Cycling & running events in Milwaukee, 2026

Milwaukee-Waukesha Training Notes

Running: Locals run the Oak Leaf Trail when they want easy Z2 without thinking, and the trail spans 76 miles through Milwaukee’s parks. Estabrook Park gives runners an almost exactly 5K loop with the Oak Leaf Trail. Milwaukee River Trail keeps things rough, with rocks, logs, and mud when rain hits. Grant Park brings singletrack along the bluff through Seven Bridges Park. Lapham Peak State Park is the crown jewel for trail runners, with loops from 1.5 miles to 6.5 miles. Milwaukee Running Group - OMG schedules 20 runs per week year round. Badgerland Striders, FrontRunners Milwaukee, and Waukesha Hash House Harriers keep the calendar busy around Lakefront Marathon, Brew City Marathon, and Schlitz Park Run by the River 5K.

Cycling: Locals ride the Hank Aaron Trail west through the Menomonee River Valley, then use the West Allis Cross Town Connector trail into Waukesha. The downtown Milwaukee to downtown Waukesha ride runs 20 miles and feels easy, fun, and surprisingly interesting. Oak Leaf Trail works for base miles, while the route south past Drexel turns into the Power Line Trail and goes all gravel to Kenosha. Muskego Recreational Trail is nearby and almost all gravel. Wild Goose State Trail and Eisenhower State Trail can make a 100-mile loop with over half gravel. Spring City Spinners ride Tuesday at 14-16 mph and keep it no-drop. Menomonee River Parkway, Grant Park, Killer Hill, and the #04602 Oak Leaf/Ozaukee Path & Back route with 437 m elevation bring the climbs.

Season: Spring, summer, and fall carry the best training rhythm here. Locals stack intervals at Shorewood High School in summer, then hit lakefront miles, Beer Run in June, Bastille Run in July, and Briggs and Stratton Run in September. Lake Michigan changes rides 90% of the time with a distinct temperature drop along the lakefront, especially in early spring, late fall, and an easterly wind. The Upper East Side route runs 5 miles. Cyclists lean harder on paved trails, indoor work, and winter classes when the roads stop feeling simple.