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Running Calendar near Highland Park 2026-2027

Monthly updates for Highland Park

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

Explore the top running races near Highland Park for 2026-2027! We've gathered 269 exciting races in the area. Check out our detailed list below to find your next local race.

Half Marathons Marathons Trail Runs Triathlons Fitness Races
May 2026
May
2
Sa

Move for MDS: Chicago

5 km
May
3
Su

Chicagoland Spring Marathon

10 km 13 mi 26 mi
May
3
Su

Tailwagger Trot

5 km
May
3
Su

Lakefront Loop 5K

5 km
May
3
Su

Bob Blazier Run For The Arts

5 km
May
3
Su

Winfield's Tiger Run

5 km
May
3
Su

Solemn Oath Brewery Run

5 km
May
9
Sa

Pink 5k

5 km
May
9
Sa

Cinco de Miler

5 mi
May
9
Sa

Mama's Run

5 km
May
9
Sa

U-46 Deaf and Hard of Hearing 5K

5 km
May
9
Sa

5K Dokie Run

5 km
May
9
Sa

Stars & Spikes: Totally Rad 5K

5 km
May
9
Sa

Girls on the Run Chicago Spring 5K

5 km
May
9
Sa

Steep Ravine Brewing Company Run

5 km
May
9
Sa

La Carrera de las Madres

5 km
May
10
Su

Barrington Mother's Day 5K

5 km
May
10
Su

Wings for Life - Chicago

5 mi
May
16
Sa

Spirits Run on the Rocks 5K - Waukegan

5 km
Spirits Run on the Rocks 5K - Waukegan A lakefront 5K in Waukegan on May 16, 2026, starting and finishing at Green Town on the Rocks. The course passes Oakwood Cemetery and the harbor, and the event includes food for participants plus post-run drinks and music.
May
16
Sa

Ducky Dash

5 km
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