October Trail Runs within 500 miles of Chaska, MN
Red Wing, MN
Bluff Color Fest Trail Run
Oct 19, 2024
Rhinelander, WI
Run for Our Heroes 5K
Oct 26, 2024
Baraboo, WI
S'more Fun Trail Run
Oct 5, 2024
Hancock, MI
Husky Autumn Mountain Run
Oct 26, 2024
Monticello, IL
Allerton Park Trail Run
Oct 27, 2024
Holland, MI
Ultra Bird Trail Races
Oct 19, 2024
Greenbush, WI
Glacial Trail 50 Mile & 50K
Oct 13, 2024
Kirksville, MO
FLATS Trail Half Marathon
Oct 5, 2024
Saint Paul, MN
Night Light
Oct 26, 2024
Suamico, WI
Stump Farm Trail Race
Oct 27, 2024
Sterling, IL
Hennepin Hundred
Oct 5, 2024
Charleston, IL
Shake Your Trail Feather Trail Run
Oct 19, 2024
Duluth, MN
Grand Traverse
Oct 5, 2024
NMTC Fall Trail Series - Rolling Stone
Oct 6, 2024
Fur-K Fun Run
Oct 12, 2024
Wild Duluth Races - Wild Duluth 100K/50K, Harder 'n Heck Half & Terribly Tough 10K
Oct 19, 2024
Oct 20, 2024
NMTC Fall Trail Series - Hawk Ridge
Oct 27, 2024
Dubuque, IA
Mines of Spain 100
Oct 18, 2024
Dyersville, IA
Haunted Heritage Trail Fun Run
Oct 13, 2024
Spring Lake, MI
North Shore Trail Run
Oct 5, 2024
East Peoria, IL
Farmdale Trail Run
Oct 12, 2024
Mason City, IA
Lime Creek Timber Trot
Oct 5, 2024
Pleasant Prairie, WI
Scary in the Prairie 5K
Oct 19, 2024
Minneapolis, MN
Loopet Loppet
Oct 19, 2024
Lemont, IL
Run with the Nuns 5K
Oct 13, 2024
Lawrence, KS
Billy Mills 10K
Oct 13, 2024
Baldwin, WI
Spooky Shuffle 2-ish Mile Fun Run
Oct 25, 2024
Lake Elmo, MN
Night Owl Races
Oct 5, 2024
Great Pumpkin Chase
Oct 20, 2024
Minocqua, WI
Buck Rut Run
Oct 20, 2024
Milwaukee, WI
River Loops - Trail Run
Oct 20, 2024
Madison, WI
Black Hawk Ridge Trail Run
Oct 20, 2024
Oswego, IL
Saw Wee Kee Fall Trail Run
Oct 19, 2024
New London, WI
Mosquito Hill Endurance Run
Oct 25, 2025
Willow Springs, IL
Universal Sole October Trail Challenge
Oct 26, 2024
Manistee, MI
HayDay Trail Run and Hike
Oct 19, 2024
Wildwood, MO
DeClue Loops Trail Race
Oct 12, 2024
La Crosse, WI
Hixon Trail Runs
Oct 26, 2024
Oct 27, 2024
Danville, IA
Geode Challenge Races
Oct 19, 2024
Delafield, WI
Lapham Peak Colorama Run
Oct 5, 2024
Galena, IL
Galena River Fall Half Marathon
Oct 26, 2024
Omaha, NE
G.O.A.T.z Trail Runs
Oct 20, 2024
Oconomowoc, WI
Zachariah's Acres Fall Trail Run/Walk/Roll
Oct 12, 2024
Sioux Falls, SD
Trick or Treat Trail Run
Oct 26, 2024
Gaylord, MI
Healing Tails Trail Run
Oct 19, 2024
Columbia, MO
Rock Bridge Revenge
Oct 12, 2024
Green Bay, WI
Run For the Hill Of It 5K
Oct 19, 2024
Albion, IN
Indiana Trail 100
Oct 12, 2024
Ashland, WI
Whistlestop Marathon
Oct 12, 2024
Cassoday, KS
Heartland
Oct 12, 2024
Oct 11, 2024
Sturgeon Bay, WI
Unmask Domestic Violence Costume Fun Run
Oct 5, 2024
Freeport, IL
Autumn Leaf Run
Oct 5, 2024
Mora, MN
Swedish Mile Trail Run
Oct 5, 2024
Center City, MN
Wild River Run
Oct 12, 2024
Hudson, IL
Run the Woods
Oct 5, 2024
Plymouth, IN
Reaper Run - Trail Race 5K and 10K
Oct 27, 2024
Sleepy Eye, MN
Nightmare Underground Fitness Trail Run
Oct 5, 2024
West Bend, WI
Race For Open Space
Oct 13, 2024
Elkader, IA
Pony Hollow Trail 15K & 5K Run
Oct 26, 2024
West Des Moines, IA
To Grandmother's House We Go
Oct 26, 2024
Steelville, MO
Ozark Trail 100 Mile Endurance Run
Oct 26, 2024
Clearwater, MN
Angel Reins 5K
Oct 12, 2024
Three Lakes, WI
Three Eagle Half Marathon & 5K
Oct 12, 2024
Savage, MN
Surf The Murph
Oct 19, 2024
Honey Creek, IA
HawkWatch Run/Walk
Oct 12, 2024
Cross Plains, WI
Indian Lake Trail Run
Oct 5, 2024
Indianola, IA
Iowa Trail Runs - Annett Nature Center
Oct 6, 2024
Houghton, MI
Tech Trails Trot
Oct 5, 2024
Rush City, MN
Hoot 'n Holler Adventure Runs
Oct 26, 2024
Grand Ledge, MI
Timber Trails 5K
Oct 12, 2024
Middleville, MI
Yankee Springs Fall Festival
Oct 5, 2024
Meriden, KS
Free State Trail Run
Oct 12, 2024
Troy, MO
Timber N Trails
Oct 27, 2024
Sylvan Grove, KS
Hell Creek 100
Oct 4, 2025
Porter, IN
Field Station Frenzy 5K
Oct 6, 2024
Vandalia, MI
Sandhill Crane All Trail Half Marathon
Oct 12, 2024
Darien, WI
Miles for Smiles
Oct 19, 2024
Lawson, MO
Wilderness Trail Trek 5K/10K
Oct 12, 2024
Peosta, IA
Swiss Valley Trail Races
Oct 4, 2025
Canton, SD
Newton Hills Trail Races
Oct 12, 2024
Dundee, IA
Backbone Trail Run
Oct 12, 2024
Strawberry Point, IA
Grotto Gallop Trail Run & Walk
Oct 19, 2024
Hinckley, MN
Fire Tower Trail Races
Oct 5, 2024
Millston, WI
Black River Trail Classic
Oct 19, 2024
Tracy, IA
Blazing the Trails 5K
Oct 12, 2024
Half Day Forest Preserve, IL
Des Plaines River Trail Races
Oct 12, 2024
Woodman, WI
Stream Walk Trail Runs
Oct 19, 2024
Shell Rock, IA
Shell Rocktoberfest
Oct 19, 2024
Pingree Grove, IL
Fall Family Fun Run
Oct 6, 2024
Sat | Sun | Mon | Tue | Wed | Thu | Fri | Multiple |
1. Hell Creek 100
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Oct 4, 2025Saturday
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140M, 100M, 100K, 20M trail run
More Information
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Sylvan Grove, KS
473 miles point to pointLincoln County, KS
2. Swiss Valley Trail Races
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Oct 4, 2025Saturday
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50K, 25K, 5.2M trail run
More Information
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Peosta, IA
218 miles point to pointDubuque County, IA
3. Autumn Leaf Run
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Past DateOct 5, 2024Saturday
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5K trail run
More Information
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Freeport, IL
272 miles point to pointStephenson County, IL
4. Fire Tower Trail Races
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Past DateOct 5, 2024Saturday
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100K, 50K, 35K, 11K trail run
More Information
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Hinckley, MN
92 miles point to pointPine County, MN
5. FLATS Trail Half Marathon
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Past DateOct 5, 2024Saturday
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13.1M trail run
More Information
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Kirksville, MO
322 miles point to pointAdair County, MO
6. Forest & Field Trail Run Lap Race
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Past DateOct 5, 2024Saturday
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10K trail run
More Information
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Spicer, MN
77 miles point to pointKandiyohi County, MN
7. Franciscan Rhythms Trail Run & Walk
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Past DateOct 5, 2024Saturday
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5K trail run | kids run
Virtual OptionMore Information
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Lowell, MI
456 miles point to pointKent County, MI
8. Grand Traverse
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Past DateOct 5, 2024Saturday
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27M, 21M, 17M, 10M trail run
More Information
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Duluth, MN
159 miles point to pointSt Louis County, MN
9. Hennepin Hundred
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Past DateOct 5, 2024Saturday
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100M, 50M, 50K trail run
More Information
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Sterling, IL
292 miles point to pointWhiteside County, IL
10. Indian Lake Trail Run
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Past DateOct 5, 2024Saturday
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10.5K, 5.8K trail run | kids run
More Information
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Cross Plains, WI
239 miles point to pointDane County, WI
11. Lapham Peak Colorama Run
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Past DateOct 5, 2024Saturday
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10K, 5K trail run | kids run
More Information
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Delafield, WI
300 miles point to pointWaukesha County, WI
12. Lime Creek Timber Trot
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Past DateOct 5, 2024Saturday
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5M trail run
More Information
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Mason City, IA
115 miles point to pointCerro Gordo County, IA
13. Night Owl Races
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Past DateOct 5, 2024Saturday
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6H, 10K, 5K trail run
More Information
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Lake Elmo, MN
40 miles point to pointWashington County, MN
14. Nightmare Underground Fitness Trail Run
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Past DateOct 5, 2024Saturday
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5K trail run
More Information
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Sleepy Eye, MN
69 miles point to pointBrown County, MN
15. North Shore Trail Run
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Past DateOct 5, 2024Saturday
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10K, 5K trail run | kids run
More Information
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Spring Lake, MI
410 miles point to pointOttawa County, MI
16. Run the Woods
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Past DateOct 5, 2024Saturday
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8K, 5K trail run
More Information
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Hudson, IL
379 miles point to pointMcLean County, IL
17. S'more Fun Trail Run
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Past DateOct 5, 2024Saturday
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13.1M, 10K, 5K, 1M trail run
More Information
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Baraboo, WI
224 miles point to pointSauk County, WI
18. Storm the Day (Sunrise to Sunset)
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Past DateOct 5, 2024Saturday
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12H trail run
More Information
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Winona, MN
114 miles point to pointWinona County, MN
19. Swedish Mile Trail Run
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Past DateOct 5, 2024Saturday
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10K, 5K trail run | kids run
More Information
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Mora, MN
77 miles point to pointKanabec County, MN
20. Tech Trails Trot
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Past DateOct 5, 2024Saturday
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10K, 5K trail run | kids run
More Information
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Houghton, MI
312 miles point to pointHoughton County, MI
For the love of all that Is good And moisture wicking...
Though we Try To be accurate And On top Of things... Race details can change When we aren't lookin. And once in a while we simply make a mistake.
ALWAYS visit the race's website for the most complete and accurate race information.
ALWAYS visit the race's website for the most complete and accurate race information.