Cycling & running events in Madison, 2026

Madison Training Notes

Running: Madison puts runners on paths fast, and you’ll see people running pretty much wherever you look. Locals use the Lake Monona Loop when they want an uninterrupted 13 miles with lake views and Capitol looks. UW-Madison Arboretum gives you 17 miles of maintained trails, and Picnic Point stays beloved for easy Z2 or a shakeout. Movin' Shoes Running Club covers Sundays, recovery runs, speed work, queer runs, womxn's runs, brewery runs, and Saturday trail runs. Fleet Feet Madison & Sun Prairie keeps free group runs simple. Run Madtown Half Marathon, Madison Marathon, Berbee Derby, Subzero Series, and XC 5k Classic anchor the calendar.

Cycling: Madison rides like a bike town because the paths actually connect. Locals use the 13-mile Lake Monona Bike Loop for base miles, quick intervals, and skyline views. The Capital City State Trail, Military Ridge State Trail, Badger State Trail, and Lower Yahara River Trail keep the Z2 days clean. The Monona stretch of the loop has short but steep hill climbs, and the far west side sits highest on a terminal moraine. Monday 40 leaves Orton Park at 6pm spring-fall, and Slow Roll Cycles rolls Tuesday at 6:20 PM from Monona Dr. Brazen Dropouts, Capital Brewery bike club, Madison Women’s Cycling Club, BBC, and Lymphomaniacs fill in the faster rides. PLAYTRI - IRONMAN WISCONSIN 140.6 is the big anchor event.

Season: Summer gives Madison its longest training runway, with June through August bringing lower-80s °F highs and long daylight. Locals stack lake loops, Capital City Trail miles, Tuesday group rides, and longer Madison Queer Bike Ride outings that can reach 30 miles. Spring and fall work well for moderate temps, race builds, gran fondo legs, and cyclocross fitness. Winter changes the kit more than the habit. Plows clear main roads quickly, bike paths usually stay clearer than street lanes, and studded tires make sense when freeze-thaw leaves ice, slush, and muck at intersections. Runners keep using sidewalks, paths, the Arboretum, and shorter club routes when the footing asks for patience.