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Trail Running Calendar near Waukesha 2026-2027

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Explore the top trail runs near Waukesha for 2026-2027! We've gathered 18 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Aug
15
Sa

Kettle Klomp

Trail Run Walk 5 km
Participate in the annual Kettle Klomp featuring a 5k run and a 2 mile walk on a scenic cross country course. This community event supports the local high school cross country team and offers awards for various age groups.
September 2026
Sep
5-6
Sa - Su

Badgerland Striders 24-12-6 Hour Runs

Backyard Ultra
Timed ultrarunning at Lapham Peak State Park with 24, 12 and 6 hour options plus a distance division for marathon and longer targets. One mile loop, chip timing, an aid station, and a cupless refill policy.
Sep
25
Fr

Echo 136

Trail Run 136 mi
Echo 136 is a 136 mile trail ultramarathon on the Ice Age State Trail in Whitewater WI with a 55 hour time limit and nine fully stocked aid stations.
Sep
26
Sa

Backyard Nonsense

Backyard Ultra
Multi-hour trail running at Richard Bong State Recreation Area offering 24, 12, 6 and 3 hour options plus a backyard 24 loop format.
Sep
27
Su

Procrastination Run

Trail Run Walk 3 mi 6 mi 13 mi
Join this trail event at Minooka Park featuring half marathon 10K and 5K distances. Participants can choose between running walking and rucking on a scenic course with shaded trails and a notable hill challenge.
October 2026
Oct
3
Sa

Lapham Peak Colorama Run/walk

Trail Run Walk 3 mi 6 mi
A fall trail event at Lapham Peak State Forest featuring timed 5K and 10K runs, accessible walk options, and a free 1K Smokey Bear run for children age 10 and under; participant shirts, awards, and post-event treats are included.
Oct
4
Su

The Milwaukee Beer Run 5k

Trail Run Walk 5 km
A community 5k and a 54 yard dash on October 4, 2026 in Glendale with an out-and-back course on the Oak Leaf Trail. Registration includes all-day entry to Milwaukee's Original Oktoberfest at Old Heidelberg Park.
Oct
10
Sa

Zachariah's Acres Fall Run

Trail Run 3 mi 13 mi
Participate in a half marathon, 5K, or rucking event at Zachariah's Acres in Oconomowoc. Support nature based programs for children with special needs while exploring prairie trails and wildflowers.
Oct
10-11
Sa - Su

Helios

Trail Run 5 km 8 km 10 km
A loop-based trail ultra in Eagle, Wisconsin offering 6, 12 and 20 hour formats for solo runners or relay teams up to four people, set on three mapped autumn loops through the Southern Kettle Moraine Forest.
Oct
11
Su

Race for Open Space - West Bend

Trail Run 5 km 10 km
Trail runs and a 1-mile walk at Fox Hill Nature Preserve on 10/11/2026, held to support conservation in the Cedar Lakes region; varied distances include 5K, 10K, a 1-mile walk, and a Kiddos 1K.
Oct
17
Sa

National Sweetest Day

Trail Run Walk 3 mi 6 mi 13 mi
National Sweetest Day at Nashotah Park on October 17, 2026 offers running, walking, and ruck events from a kids 1K to a half marathon. Entry fees vary and several events include post race treats.
Oct
31
Sa

Among the Trees

Trail Run 50 km 100 km
Experience the historic Ice Age Trail during this autumn ultramarathon in the Southern Kettle Moraine Forest. Choose between 50k and 100k distances featuring on site branded wooden medals and scenic fall colors.
November 2026
Nov
6-8
Fr - Su

tBunk Endurance Challenge

Trail Run 15 km 50 km ... 150 mi 200 mi
A multi-distance trail event in Southern Kettle Moraine State Forest offering ultra distances, a 50K and a 15K Fun Run, with aid stations, pacing rules, finisher awards, and proceeds funding forest projects.
Nov
7
Sa

Warrior 8K Through the Park

Trail Run 5 km 8 km
Trail runs and a walking option use a rolling park course that starts at the southwest corner and returns through woods, service road, and open sections with occasional rough footing and visible seasonal foliage.
Nov
14
Sa

Bucks & Does 13.1

Trail Run 3 mi 6 mi 13 mi
Bucks & Does 13.1 Pointer is a multi-distance running, walking, and ruck event at Nashotah Park on 11/14/2026. Distances range from a youth Bambi Run to a 13.1 Pointer, and every finisher receives a wooden finisher medal.
February 2027
Feb
27-28
Sa - Su

ARKTOS

Backyard Ultra
A winter timed ultra in the Southern Kettle Moraine Forest offering 6, 12 and 24 hour loop options for solo runners and relay teams. The field is limited to 160 participants and the 6 hour option is available in AM and PM waves.
April 2027
Apr
4
Su

Trailbreaker

Trail Run 3 mi 6 mi ... 20 mi 26 mi
Trailbreaker returns to Waukesha on April 4, 2027 with races from a 1K kids run to a full marathon, plus ruck options and a walk. Proceeds support the Park Foundation of Waukesha and local parks and recreation.
October 2027
Oct
9
Sa

Ultratrax Alpine Valley

Trail Run Walk 7 mi 14 mi 21 mi 28 mi
Multi-loop fall trail event at Alpine Valley near Elkhorn WI with a 7 mile loop, optional weighted rucks, and finish awards including the Grey Wolf medal.
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