Upcoming Races Near Sleepy Hollow, IL

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Lawndale 5K

Chicago, IL

Saturday, September 26th, 2026

View details for race Lawndale 5K

Christmas Clearing Council Jingle Bell Jog and ...

Pewaukee, WI

Saturday, September 26th, 2026

Trail

View details for race Christmas Clearing Council Jingle Bell Jog and Walk

Stone Bridge Half Marathon and 5k

Roscoe, IL

Saturday, September 26th, 2026

Half

Trail

Fast

View details for race Stone Bridge Half Marathon and 5k

Race to Cure Sarcoma Chicago

Chicago, IL

Saturday, September 26th, 2026

View details for race Race to Cure Sarcoma Chicago

Walk Run Wag 2026 for MADACC - Barktoberfest Ed...

Milwaukee, WI

Saturday, September 26th, 2026

View details for race Walk Run Wag 2026 for MADACC - Barktoberfest Edition!

St. Jude Walk-Chicago

Brookfield, IL

Saturday, September 26th, 2026

View details for race St. Jude Walk-Chicago

Bloomingdale Trail 5K

Chicago, IL

Saturday, September 26th, 2026

Trail

View details for race Bloomingdale Trail 5K

Fall Color Festival

Whitewater, WI

Saturday, September 26th, 2026

Ultra

Half

1 Mile

Trail

View details for race Fall Color Festival

I’m Here for the Food (Pantry) 5k

Elk Grove Village, IL

Saturday, September 26th, 2026

View details for race I’m Here for the Food (Pantry) 5k

Lake County Suicide Prevention Task Force 14th ...

Grayslake, IL

Saturday, September 26th, 2026

View details for race Lake County Suicide Prevention Task Force 14th Annual 5K Walk/Run for Awareness and Suicide Prevention

Healthy Kids Running Series Fall 2026 - La Gran...

Countryside, IL

Sunday, September 27th, 2026

View details for race Healthy Kids Running Series Fall 2026 - La Grange/Countryside, IL

Northwest CASA Pumpkin Dash 5k / 10k

Elk Grove Village, IL

Sunday, September 27th, 2026

10K

View details for race Northwest CASA Pumpkin Dash 5k / 10k

Golden Harvest Half Marathon & 5k/10k - Greater...

Greater Chicago, IL

Sunday, September 27th, 2026

1 Mile

10K

View details for race Golden Harvest Half Marathon & 5k/10k - Greater Chicago

Soph's Legacy Loop - Reach for the Sky!

Lockport, IL

Sunday, September 27th, 2026

1 Mile

View details for race Soph's Legacy Loop - Reach for the Sky!

Lester Fun Run 2025

Downers Grove, IL

Sunday, September 27th, 2026

1 Mile

View details for race Lester Fun Run 2025

DeKalb Corn Classic

DeKalb, IL

Sunday, September 27th, 2026

10K

View details for race DeKalb Corn Classic

Run the River for Respect 5K

Ottawa, IL

Sunday, September 27th, 2026

View details for race Run the River for Respect 5K

Plainfield Harvest Run 5k/10k & Kids Miler

Plainfield, IL

Sunday, September 27th, 2026

1 Mile

10K

View details for race Plainfield Harvest Run 5k/10k & Kids Miler

F3 Naperville 5K Run & Walk for Little Friends

Warrenville, IL

Sunday, September 27th, 2026

View details for race F3 Naperville 5K Run & Walk for Little Friends

2026 Chi-Care 5K Run/Walk

Chicago, IL

Sunday, September 27th, 2026

View details for race 2026 Chi-Care 5K Run/Walk

The Grant Heffelfinger Memorial Big Gay 5K

Milwaukee, WI

Sunday, September 27th, 2026

View details for race The Grant Heffelfinger Memorial Big Gay 5K

4th Annual Ted's Run 5k

Racine, WI

Sunday, September 27th, 2026

View details for race 4th Annual Ted's Run 5k

Procrastination Run

Waukesha, WI

Sunday, September 27th, 2026

Half

10K

View details for race Procrastination Run

Angels Against Abuse 5K Walk/Run

Romeoville, IL

Saturday, October 3rd, 2026

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

2026 Milwaukee Lakefront Marathon

Milwaukee, WI

Saturday, October 3rd, 2026

Marathon

View details for race 2026 Milwaukee Lakefront Marathon

Long Grove's Prairie State Half Marathon, 10K &...

Long Grove, IL

Saturday, October 3rd, 2026

Half

10K

View details for race Long Grove's Prairie State Half Marathon, 10K & Oktoberfest 5K

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

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

Fall into Fall Trail 5k Run/Walk

Janesville, WI

Saturday, October 3rd, 2026

Trail

View details for race Fall into Fall Trail 5k Run/Walk

Boo Island - 5K Charity Run/Walk

Blue Island, IL

Saturday, October 3rd, 2026

Trail

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

Hops for Hope 5K & BrewFest Presented by 93 Oct...

St. Charles, IL

Saturday, October 3rd, 2026

View details for race Hops for Hope 5K & BrewFest Presented by 93 Octane Brewery 2026

Sweet Ride | Bike • Run • Walk

Willow Springs, IL

Saturday, October 3rd, 2026

Trail

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

Wisconsin Cheese Run

Muskego, WI

Saturday, October 3rd, 2026

View details for race Wisconsin Cheese Run

Lapham Peak Colorama Run/Walk

Delafield, WI

Saturday, October 3rd, 2026

10K

Trail

View details for race Lapham Peak Colorama Run/Walk

Diplo's Run Club Chicago

Chicago, IL

Saturday, October 3rd, 2026

Code:FTR10

View details for race Diplo's Run Club Chicago

Autumn Leaf Run

Freeport, IL

Saturday, October 3rd, 2026

Trail

View details for race Autumn Leaf Run

The Milwaukee Beer Run 5k & .05k

Glendale, WI

Sunday, October 4th, 2026

Trail

View details for race The Milwaukee Beer Run 5k & .05k

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

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

Fire Zone 5k

Lockport, IL

Sunday, October 4th, 2026

Trail

View details for race Fire Zone 5k

Chicago - HFTC 5k

Chicago, IL

Sunday, October 4th, 2026

View details for race Chicago - HFTC 5k

JJC Foundation 5K Run/Walk

Joliet, IL

Sunday, October 4th, 2026

1 Mile

View details for race JJC Foundation 5K Run/Walk

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

Sauk Valley Apple Cider Run

Rock Falls, IL

Saturday, October 10th, 2026

Half

View details for race Sauk Valley Apple Cider Run

13th Annual Harvest Hustle 5K

Niles, IL

Saturday, October 10th, 2026

View details for race 13th Annual Harvest Hustle 5K

Welcome Run 5K

Lansing, IL

Saturday, October 10th, 2026

View details for race Welcome Run 5K

El Trote De Las Calacas

Elgin, IL

Saturday, October 10th, 2026

View details for race El Trote De Las Calacas

Zachariah's Acres Fall Run, Walk & Roll

Oconomowoc, WI

Saturday, October 10th, 2026

Half

View details for race Zachariah's Acres Fall Run, Walk & Roll

4th Annual YMCA Run For The Hills 5K/2K

Crown Point, IN

Saturday, October 10th, 2026

View details for race 4th Annual YMCA Run For The Hills 5K/2K

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)

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