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Trail Running Calendar near Oconomowoc 2026-2027

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Explore the top trail runs near Oconomowoc for 2026-2027! We've gathered 22 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

September 2026
Sep
25
Fr

Echo 136

Trail Run 136 mi
Echo 136 is a 136 mile point to point journey along the Ice Age State Trail in Wisconsin featuring 11,148 feet of elevation gain and a 55 hour time limit.
Sep
26
Sa

Emmy's Rustic Run

Trail Run 5 km
A 10th annual farm-based 5k trail run and family day in Fort Atkinson, WI supporting A-T research with in-person and virtual participation options.
Sep
27
Su

Procrastination Run

Trail Run 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 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

Frosty Rock Challenge

Road Race Trail Run 5 km 12 km
The 14th annual Frosty Rock Challenge in Fort Atkinson offers a 12k, a 5k and a free 1 mile walk run with proceeds supporting local and international Rotary 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
18
Fr

Quiet Silence

Trail Run 18 mi 31 mi
Embrace the winter night on a flat rails to trails course in Lake Mills with 17.5 or 31 mile distances and a unique quiet atmosphere.
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.
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