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Trail Running Calendar near Wheeling 2025-2026

Explore the top trail runs near Wheeling for 2025-2026! We've gathered 34 exciting races in the area. Check out our detailed list below to find your next local race.

May 2025
May
3
Saturday

Fight Hunger 10K

5 km 10 km
May
3
Saturday

Windmill Whirl

5 km
May
3
Saturday

HOH 5K Run/Walk

5 km
May
4
Sunday

Great Western Half-Marathon & 10K

Trail Run 10 km 13 mi
May
4
Sunday

Chicagoland Spring Marathon

10 km 13 mi 26 mi
May
4
Sunday

Tailwagger Trot

5 km
May
10
Saturday

Pink 5k

5 km
May
10
Saturday

RMS Color Fun Run 5K

5 km
May
10
Saturday

U-46 Deaf and Hard of Hearing 5K

5 km
May
11
Sunday

Barrington Mother's Day 5K

5 km
May
17
Saturday

Ducky Dash

5 km
May
17
Saturday

Run for D103 5K

5 km
May
17
Saturday

Chicago 11 Hour Endurance Run

Backyard Ultra 7 hr 11 hr
May
17
Saturday

Run the Hills 5k

5 km
May
17
Saturday

Race for Peace 5K

5 km
May
18
Sunday

Chicago Spring Half Marathon

10 km 21 km
May
18
Sunday

Dash for the Dogs 5K

5 km
May
24
Saturday

Western Springs Tower Trot

5 km 10 km
May
25
Sunday

The Memorial 5K

5 km
May
25
Sunday

Race to the Flag

5 km
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