Upcoming Races Near Sleepy Hollow, IL

Organize a race? Get it in front of thousands of runners.

Add it free Feature it

3rd Annual Downers Grove, IL Ostomy 5k

Downers Grove, IL

Saturday, October 3rd, 2026

View details for race 3rd Annual Downers Grove, IL Ostomy 5k

Angels Against Abuse 5K Walk/Run

Romeoville, IL

Saturday, October 3rd, 2026

View details for race Angels Against Abuse 5K Walk/Run

Boo Island - 5K Charity Run/Walk

Blue Island, IL

Saturday, October 3rd, 2026

Trail

View details for race Boo Island - 5K Charity Run/Walk

Haunted Wine Run 5k at Busse Woods

Elk Grove Village, IL

Saturday, October 3rd, 2026

Fast

View details for race Haunted Wine Run 5k at Busse Woods

Sweet Ride | Bike • Run • Walk

Willow Springs, IL

Saturday, October 3rd, 2026

Trail

View details for race Sweet Ride | Bike • Run • Walk

Diplo's Run Club Chicago

Chicago, IL

Saturday, October 3rd, 2026

Code:FTR10

View details for race Diplo's Run Club Chicago

JJC Foundation 5K Run/Walk

Joliet, IL

Sunday, October 4th, 2026

1 Mile

View details for race JJC Foundation 5K Run/Walk

Cheesy Pretzel 5K and 1 Mile Walk

Bolingbrook, IL

Sunday, October 4th, 2026

1 Mile

View details for race Cheesy Pretzel 5K and 1 Mile Walk

13th Annual Head for the Cure 5K - Chicago

Chicago, IL

Sunday, October 4th, 2026

View details for race 13th Annual Head for the Cure 5K - Chicago

Fire Zone 5k

Lockport, IL

Sunday, October 4th, 2026

Trail

View details for race Fire Zone 5k

2026 Lemons of Love Pink Lemonade 5K Run/Walk

Mount Prospect, IL

Sunday, October 4th, 2026

View details for race 2026 Lemons of Love Pink Lemonade 5K Run/Walk

Chicago - HFTC 5k

Chicago, IL

Sunday, October 4th, 2026

View details for race Chicago - HFTC 5k

Care4 Breast Cancer Hybrid 5K

Woodstock, IL

Saturday, October 10th, 2026

View details for race Care4 Breast Cancer Hybrid 5K

Nik's 7K Home Run & 1.5 Mile Walk & Grammy's Au...

Loves Park, IL

Saturday, October 10th, 2026

1 Mile

View details for race Nik's 7K Home Run & 1.5 Mile Walk & Grammy's Auction at MercyHealth Sportscore Two (Indoor Sports Center)

El Trote De Las Calacas

Elgin, IL

Saturday, October 10th, 2026

View details for race El Trote De Las Calacas

12th Annual Harvest Hustle 5K

Niles, IL

Saturday, October 10th, 2026

View details for race 12th Annual Harvest Hustle 5K

2026 Bank of America Chicago Marathon

Chicago, IL

Sunday, October 11th, 2026

Marathon

View details for race 2026 Bank of America Chicago Marathon

Chicago Fall Classic Half Marathon, 10K & Hot C...

Chicago, IL

Saturday, October 17th, 2026

Half

10K

View details for race Chicago Fall Classic Half Marathon, 10K & Hot Cider Hustle 5K

Rosehill Cemetery 'Crypt' 5K Run/Walk

Chicago, IL

Saturday, October 17th, 2026

View details for race Rosehill Cemetery 'Crypt' 5K Run/Walk

Cantigny 5K Run/Walk 2026 - Benefiting The Midw...

Wheaton, IL

Saturday, October 17th, 2026

1 Mile

View details for race Cantigny 5K Run/Walk 2026 - Benefiting The Midwest Shelter for Homeless Veterans

JAIMIE COX MEMORIAL RUN

Roscoe, IL

Saturday, October 17th, 2026

Trail

View details for race JAIMIE COX MEMORIAL RUN

Bolingbrook Howl-O-Ween 5K

Bolingbrook, IL

Sunday, October 18th, 2026

View details for race Bolingbrook Howl-O-Ween 5K

23rd Annual This Run's For Jack 2026

Glen Ellyn, IL

Sunday, October 18th, 2026

View details for race 23rd Annual This Run's For Jack 2026

Richardson Farm Fall 5K & 10K with Family 1 Mil...

Spring Grove, IL

Sunday, October 18th, 2026

10K

1 Mile

Fast

View details for race Richardson Farm Fall 5K & 10K with Family 1 Mile Adventure Run

Haunted Highlander Assault Trail Run

Mchenry, IL

Friday, October 23rd, 2026

Trail

View details for race Haunted Highlander Assault Trail Run

Haunted Highlander Assault Trail Run

Pingree Grove, IL

Friday, October 23rd, 2026

Trail

View details for race Haunted Highlander Assault Trail Run

Halloween Hustle 5K & Kids Dash

Palatine, IL

Saturday, October 24th, 2026

View details for race Halloween Hustle 5K & Kids Dash

Lake Bluff PTO Pumpkin Chase

Lake Bluff, IL

Saturday, October 24th, 2026

1 Mile

View details for race Lake Bluff PTO Pumpkin Chase

Run to Pub Fall Marathon Relay

Tinley Park, IL

Saturday, October 24th, 2026

View details for race Run to Pub Fall Marathon Relay

The Fall Color 5K

Lisle, IL

Saturday, October 24th, 2026

View details for race The Fall Color 5K

Badger High School 5K GLOW Run/Walk

Lake Geneva, WI

Saturday, October 24th, 2026

View details for race Badger High School 5K GLOW Run/Walk

Forte 5K Run/Walk

Channahon, IL

Saturday, October 24th, 2026

View details for race Forte 5K Run/Walk

Run to Pub Marathon Volunteer

Tinley Park, IL

Saturday, October 24th, 2026

View details for race Run to Pub Marathon Volunteer

Batavia United Way Bat Race 5K & 10K

Batavia, IL

Saturday, October 24th, 2026

10K

View details for race Batavia United Way Bat Race 5K & 10K

Scary in the Prairie 5k

Pleasant Prairie, WI

Saturday, October 24th, 2026

View details for race Scary in the Prairie 5k

Howl-o-ween 5k - Schaumburg

Rolling Meadows, IL

Saturday, October 24th, 2026

View details for race Howl-o-ween 5k - Schaumburg

Fraidycat 5k,8k & Meow Mile

Oswego, IL

Sunday, October 25th, 2026

1 Mile

View details for race Fraidycat 5k,8k & Meow Mile

Haunted Halloween Half Marathon & 5km

Chicago, IL

Sunday, October 25th, 2026

Half

Trail

View details for race Haunted Halloween Half Marathon & 5km

Howl-o-ween 5k - Dan Ryan Woods

Chicago, IL

Sunday, October 25th, 2026

View details for race Howl-o-ween 5k - Dan Ryan Woods

Hot Cider Hustle - Wheaton 8 Mile Run & 5K Run/...

Wheaton, IL

Sunday, October 25th, 2026

View details for race Hot Cider Hustle - Wheaton 8 Mile Run & 5K Run/Walk

Day of the Dead Family 5K Run/Walk

Wheeling, IL

Sunday, October 25th, 2026

View details for race Day of the Dead Family 5K Run/Walk

Spooky Sprint - Greater Chicago

Shorewood, IL

Sunday, October 25th, 2026

1 Mile

10K

View details for race Spooky Sprint - Greater Chicago

Spooky Sprint - Greater Chicago

Greater Chicago, IL

Sunday, October 25th, 2026

1 Mile

10K

View details for race Spooky Sprint - Greater Chicago

Haunted Oak 5K

Homer Glen, IL

Sunday, October 25th, 2026

View details for race Haunted Oak 5K

St. Francis Xavier Falcon 5K Run/Walk

La Grange Park, IL

Saturday, November 7th, 2026

View details for race St. Francis Xavier Falcon 5K Run/Walk

Jingle Bell Run Illinois

JingleBell, IL

Sunday, November 8th, 2026

View details for race Jingle Bell Run Illinois

2026 Jingle Bell Run - Western Suburbs, IL

Wheaton, IL

Saturday, November 14th, 2026

1 Mile

View details for race 2026 Jingle Bell Run - Western Suburbs, IL

Brookfield Zoo Chicago Reindeer Run

Brookfield, IL

Saturday, November 14th, 2026

View details for race Brookfield Zoo Chicago Reindeer Run

The Forge Trail Run Festival

Lemont, IL

Saturday, November 14th, 2026

10K

Half

Trail

View details for race The Forge Trail Run Festival

Abominable Trail Race

Lake Geneva, WI

Saturday, November 14th, 2026

10K

15K

Trail

View details for race Abominable Trail Race

Prev 2 35 6 Next

Explore more in Sleepy Hollow, IL

Jump straight to races by distance, month, or type.

Distance

5K 10K Half Marathon Marathon

Month

June July August

Race type

Trail Boston Qualifiers Fast Courses

Run clubs

Run clubs in Sleepy Hollow

Nearby

Elgin Hoffman Estates Palatine McHenry Elk Grove Village Arlington Heights All Illinois races