Trail RunningIllinois
Trail Running in Illinois
Browse upcoming amateur trail running events and compare dates, locations, and popularity. in Illinois.
Upcoming dates Illinois Community-rated events
Events listed
96
Sport
Trail Running
Area
Illinois
Radius
350 km
This calendar in numbers
This calendar currently lists 96 upcoming events, from Aug 13, 2026 to May 29, 2027. August is the busiest month, with 26 events scheduled. Events are spread across 85 different locations; Chicago hosts the most (5). Course distances range from 5 km to 21.1 km.
Browse all 96 events by date
August 2026
- Summer Trail Series Race #4 – 5K Aug 13
- 2026 New Glarus Woods Trail Run Aug 15
- 3 Legged Monster Aug 15
- 3 Legged Monster Race Aug 15
- 40/50 Mile Challenge – Busse Woods Aug 15
- Buckner Park Dash-Kid Race Aug 15
- Corn Roast Fun Trail Run Aug 15
- DINO Trail Run – SouthWestWay Aug 15
- DINO Trail Run SouthWestWay Indianapolis Aug 15
- IDES 5K Run/Walk for Hunger Aug 15
- New Glarus Woods State Park Trail Run Aug 15
- No Fear All Fun Aug 15
- RAMP River Run Aug 15
- Summer Night Trail Run Aug 15
- The Next Loop Endurance Series -Busse Woods Aug 15
- Trystan's Backyard Ultra Aug 15
- Royal Oaks Sunrise Trail Race Aug 22
- Run The Hawk Trail Run Aug 22
- Run the Hawk Trail Runs Aug 22
- Shawnee Hills 100 Aug 22
- Shawnee Hills Trail Races Aug 22
- Summer Trail Classic Aug 23
- Corps of Discovery Half Marathon, 8 Mile & 5 Mile Aug 29
- ScoCo50 Aug 29
- The Labor Day Slay Aug 29
- VICTORY LANE BACKYARD 12 Aug 29
September 2026
- Badgerland 24, 12 & 6 Hour Run Sep 5
- Naperville Trails Half Marathon Sep 5
- Prairie Dog Trail Run Sep 5
- Prairie Dog Trail Run Sep 5
- Temptation 200 Ultras Sep 5
- 4th Annual Greendale Run for the Parks and Trails Sep 6
- Wisconsin ANVIL Ultra Triathlon Sep 9
- Dash for Donuts Sep 12
- Joe's Run, Walk and Roll Sep 12
- Mt. Baldhead Challenge Sep 12
- Mutt Strut Sep 12
- Pleasant Creek Trail Run Sep 12
- Prairie On Fire Backyard Ultra Sep 12
- Timely Nonsense Sep 12
- Sorta Mountain Stage Race Sep 13
- Last Dot Standing Sep 18
- Broken Anvil Backyard Ultra Sep 19
- Adrenaline Races Sep 20
- Bloomingdale Trail 5K Sep 26
- Centerstone Life;Story 5K - Marion, IL Sep 26
- Run for the Hills Sep 26
- SIUE Cougars Unleashed Homecoming Run & Pancake Breakfast Sep 26
- ZERO Prostate Cancer Run/Walk Chicago SEA Blue Sep 26
- F3 Naperville Foundation 5K Sep 27
October 2026
- Paint the Town Pink Oct 1
- 5K Your Ways Oct 3
- Autumn Leaf Run Oct 3
- Boo Island - 5K Charity Run/Walk Oct 3
- Field Station Frenzy 5K Trail Run Oct 3
- FLATS Trail Half Marathon Oct 3
- Hops for Hope 5K & BrewFest Oct 3
- Long Grove's Prairie State Oktober Fest 5K Oct 3
- S'More Fun Trail Run Oct 3
- The Hennepin Hundred Oct 3
- Trail Run at Indian Lake Oct 3
- Tryon Farm 4 Miler/8 Miler/25k/50k and 2 mile Fun Run/Walk Oct 3
- 20th Annual Run for Riley 5 Mile & 5K Oct 4
- Owen Valley Haunted Wine Run 5k Oct 4
- Race For Open Space Oct 11
- Mines of Spain 100 Oct 16
- Shake Your Trail Feather Trail Run Oct 16
- Chicago Fall Classic Half Marathon 10K & 5K Oct 17
- Overdose Lifeline 5K Oct 17
- Rosehill Cemetery Crypt 5K Oct 17
- Saw Wee Kee - Fall Trail Run Oct 17
- Black Hawk Ridge Run Oct 18
- Run with the Nuns 5K Oct 18
- Wheaton Hot Cider Hustle Oct 25
November 2026
- The EQUALIZER 50K and 100K Gravel Race Nov 7
- WOOF Trail Run 2026 Nov 7
- City of the Sun 5K Trail Run 2026 Nov 8
- Squatch Till You Drop Nov 8
- Bigfoot Half Trail Run Nov 14
- Tunnel Hill 100 Nov 14
- Woodpecker Six Nov 14
- 32nd Annual Turkey Trot 5K Nov 21
- Meandering Turkey Nov 22
- 2026 Thanksgiving Trail Trot Nov 26
- Racine Turkey Trot 5K Nov 26
- FOLEPI River Trail Classic Nov 28
- Trail Trot on Turkey Ridge Nov 28
January 2027
February 2027
April 2027
- The Trailbreaker Apr 4
- Loud Thunder 50 Apr 14
- Tour de Dodge Apr 17
May 2027
- Sugar Badger 50/50 and Half May 29