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Trail Running Calendar near Near South Side 2026-2027

Monthly updates for Near South Side

Get new running races (and updates) in your inbox every month.

Explore the top trail runs near Near South Side for 2026-2027! We've gathered 11 exciting races in the area. Check out our detailed list below to find your next local race.

January 2026
Jan
31
Sa

Frozen Tundra 5K

Trail Run 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 10 mi 26 mi
June 2026
Jun
20
Sa

Gifts of Love Community 5K

Trail Run 5 km 4 mi
Jun
27
Sa

YMCA Brickyard Run 5mi

Trail Run 5 km 5 mi
September 2026
Sep
5
Sa

Naperville Trails Half Marathon

Trail Run 10 km Half Marathon
October 2026
Oct
10
Sa

Des Plaines River Trail Races

Trail Run 13 mi 26 mi 50 km 50 mi
Oct
24
Sa

Fancy Nonsense 25K/50K

Trail Run 5 mi 25 km 50 km
November 2026
Nov
14
Sa

The Forge Trail Run Festival

Trail Run 10 km 20 km 30 km 60 km