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Trail Running Calendar near Streeterville 2025-2026

Explore the top trail runs near Streeterville for 2025-2026! We've gathered 10 exciting races in the area. Check out our detailed list below to find your next local race.

November 2025
Nov
27
Th

Orland Park Turkey Trot
Trail Run 3 mi
Nov
27
Th

Winnetka Turkey Trot
Trail Run 5 km
Nov
29
Sa

Northeast XC Championships
Trail Run 3 km 5 km
Nov
30
Su

Chicago Gaelic Park Carraig Challenge Cross Country 5K Run
Trail Run 2 mi 5 km
March 2026
Mar
14
Sa

Muddy Shamrock @ The Forge
Trail Run 7 mi 13 mi
Mar
28
Sa

Chauncey's 4 at The Farm
Trail Run 4 mi
April 2026
Apr
25
Sa

Childish Nonsense
Trail Run 10 km 25 km 50 km 50 mi
May 2026
May
9
Sa

F^3 Cap Sauers Trail Marathon
Trail Run
June 2026
Jun
20
Sa

Gifts of Love Community 5K
Trail Run 5 km
November 2026
Nov
14
Sa

The Forge Trail Run Festival
Trail Run 10 km 20 km 30 km 60 km