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Trail Running Calendar near Richmond Township 2026-2027

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Explore the top trail runs near Richmond Township for 2026-2027! We've gathered 25 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Aug
8
Sa

40/50 Mile Challenge - Deer Grove East

Trail Run 40 mi 50 mi
A continuous loop trail race at Deer Grove East Forest Preserve in Palatine IL offering 40 or 50 mile distances on a 3.1 mile loop with full aid support.
Aug
8
Sa

The Next Loop - Deer Grove East

Trail Run 5 km 10 km ... 40 mi 50 mi
Loop-format trail event at Deer Grove East Forest Preserve offering distances from 5K to 50K plus continuous 40 mile and 50 mile challenges with central aid.
Aug
15
Sa

Highlander Assault Obstacle Race

Obstacle Run 3 km 5 km 15 km
Awarded OCR Buddy People's Choice, Highlander Assault in Pingree Grove IL offers 3K, 5K and 15K obstacle heats plus night and haunted 5K events.
Aug
23
Su

Summer Trail Classic

Trail Run Walk 4 mi 10 mi 13 mi
Trail races at Paul Douglas Preserve offering approximate 4, 9.5 and 13 mile single-track courses as part of the Dick Pond Athletics Darn Tough Trail Race Series.
Aug
29
Sa

Tough Mudder - Chicago

Obstacle Run 5 km 15 km
A mud obstacle event on August 29, 2026 at Richardson Adventure Farm offering 5K, 15K, timed Infinity laps, Mudder Village, and finisher rewards.
Aug
29
Sa

40/50 Mile Challenge - Half Day Forest Preserve

Trail Run 40 mi 50 mi
Aug
29
Sa

The Next Loop - Half Day Forest Preserve

Trail Run 5 km 10 km ... Marathon 50 km
Loop based trail event at Half Day Forest Preserve where runners repeat a 3.1 mile loop, stop after any loop with no penalty, and receive official timing for each completed loop for combined results.
September 2026
Sep
11
Fr

Woodland ROAR Run

Road Race Trail Run Walk 5 km
A community run at Woodland Middle School in Gurnee on September 11, 2026, offering a 5K, 1 Mile, and a shirt only option. Proceeds support the Woodland PTA and confidential financial assistance for fees is available.
Sep
26
Sa

Moraine Hills Run for the Hills

Trail Run Walk 5 km 10 km 13 mi
In-person and virtual 5K, 10K and half marathon at Moraine Hills State Park with marked trails, water stations, and proceeds supporting park programs.
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.
October 2026
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
17
Sa

Soul Crusher

Trail Run 5 mi 10 mi
Trail race in Crystal Lake on single-track loops of about 5 and 10 miles, marked course, race shirt and finisher medals; cup-less event.
Oct
18
Su

Richardson Farm Fall 10K with Family Adventure Run

Trail Run Walk 5 km 10 km
Oct 18, 2026 in Spring Grove: run through a corn maze and farm with 10K, 5K including a 250 turn maze option and a 1 mile Family Adventure, plus finisher medals.
Oct
23
Fr

Haunted Highlander Assault Trail Run

Trail Run 5 km
A Halloween-themed trail event in Pingree Grove, IL on October 23, 2026 with multiple 5 km heats, haunted sets and animatronics, plus a costume contest, bonfire and food; spectator fee $10, free parking.
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
14
Sa

Abominable Trail Race

Trail Run 5 km 10 km 15 km 30 km
On 11/14/2026 the Abominable Trail Race at Lake Geneva Ziplines & Adventures offers 5K, 10K, 15K and 30K courses plus 2, 3 or 4 person 30K relays on forest trails, with water stations, race shirt, finisher medal and free action photos.
Nov
14
Sa

Nikki Cozzi-Carso Scholarship 5K

Road Race Trail Run Walk 5 km
An annual canicross friendly 5K at Deer Grove-East in Palatine on November 14 2026 supporting a local scholarship fund, with awards, refreshments and a paved course option.
Nov
28
Sa

Midwest XC Championships

Trail Run 3 km 5 km
Regional cross country championships in Kenosha, WI on November 28, 2026, featuring multiple 5K races and a 3K youth event. Top finishers in the championship race can qualify for the Brooks XC National Championships in San Diego.
December 2026
Dec
13
Su

Cold Coding

Trail Run 4 mi 8 mi
A Canicross-focused trail event at Lake Geneva with 4- and 8-mile loop options, basic aid, and dog-specific awards.
January 2027
Jan
9
Sa

Frozen Gnome

Trail Run 10 km 50 km
Winter trail race in Crystal Lake with a hilly single-track 10K loop and a 50K made of five laps, staffed aid stations, finisher medals, and age-group awards.
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