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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 20 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

October 2026
Oct
3
Sa

Lapham Peak Colorama Run/walk

Trail Run 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 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, Walk & Roll

Trail Run 3 mi 6 mi 13 mi
Community running, rucking, and family walking event on October 10, 2026 in Oconomowoc, with proceeds supporting children with special needs.
Oct
10-11
Sa - Su

Helios

Trail Run 3 mi 5 mi 6 mi
Six, 12 and 20 hour trail ultras in the Southern Kettle Moraine Forest with three loop options, solo or relay teams, and a village basecamp.
Oct
10
Sa

Backyard Run / Walk for the Animals

Backyard Ultra
Looped fundraising run and walk at Another Chance Ranch in Neosho, WI offering distances from a few miles to a marathon and beyond, with a $35 registration donation.
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 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 5K & 8K Through the Park

Trail Run 5 km 8 km
Trail runs and a 2.25 mile walk through rolling park trails and wooded sections in West Allis.
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.
December 2026
Dec
26
Sa

GrindFest Progression Run

Road Race Backyard Ultra
A progression run on a 443 m indoor track at Pettit National Ice Center on 12/26/2026 where pace increases every three laps until one runner remains.
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.
May 2027
May
8
Sa

Ice Age Trail 50

Trail Run Half Marathon 50 km 50 mi
One of the oldest continuously running ultras in the country, Ice Age Trail 50 runs through glacial terrain and offers 50 mile, 50K and half marathon distances.
May
29
Sa

Bunk House Trail Runs

Trail Run 10 km 30 km 50 km
Trail races at Scuppernong Trailhead in Dousman, WI offering 50K, 30K and 10K on a 10K+ loop with an aid station, cupless policy, and proceeds supporting Kettle Moraine projects.
August 2027
Aug
14-15
Sa - Su

Run S'more 24

Road Race Trail Run Backyard Ultra 3 mi 6 mi ... 50 km 50 mi
A 24 hour event at Nashotah Park with solo and relay options plus a range of fixed distance runs and ruck events, camping and evening activities.
Aug
14
Sa

Kettle Klomp

Trail Run 5 km
Community run and walk at Kettle Moraine Lutheran High School featuring a two-loop 5 km, a 2 mile walk, and a 400 m kids run.
September 2027
Sep
24
Fr

Echo 136

Trail Run 136 mi
A roughly 136 mile ultramarathon on the Ice Age Trail near Whitewater WI with nine aid stations, a 55 hour limit, required FarOut offline maps and specific pacer and crew rules.
October 2027
Oct
9
Sa

Ultratrax Alpine Valley

Trail Run 7 mi 14 mi 21 mi 28 mi
Timed 10 hour trail event at Alpine Valley, Elkhorn WI with clearly marked single track loops of 7, 14, 21 and 28 miles and optional weighted divisions.
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