Upcoming Races Near Winnetka, IL

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Bayside Five and Wine

Bayside, WI

Saturday, September 26th, 2026

View details for race Bayside Five and Wine

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

LCSPTF 14th Annual 5K

Grayslake, IL

Saturday, September 26th, 2026

View details for race LCSPTF 14th Annual 5K

Sandhill Shuffle 5k Run/Walk

Wheatfield, IN

Saturday, September 26th, 2026

View details for race Sandhill Shuffle 5k Run/Walk

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!

Bloomingdale Trail 5K

Chicago, IL

Saturday, September 26th, 2026

Trail

View details for race Bloomingdale Trail 5K

The Grant Heffelfinger Memorial Big Gay 5K

Milwaukee, WI

Sunday, September 27th, 2026

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

2026 Chi-Care 5K Run/Walk

Chicago, IL

Sunday, September 27th, 2026

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

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

DeKalb Corn Classic

DeKalb, IL

Sunday, September 27th, 2026

10K

View details for race DeKalb Corn Classic

Lester Fun Run 2025

Downers Grove, IL

Sunday, September 27th, 2026

1 Mile

View details for race Lester Fun Run 2025

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 - In the Clouds

Lockport, IL

Sunday, September 27th, 2026

1 Mile

View details for race Soph's Legacy Loop - In the Clouds

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

Fall Fest 5K and Kids Fun Run

Stillman Valley, IL

Sunday, September 27th, 2026

View details for race Fall Fest 5K and Kids Fun Run

F3 Naperville 5K Run & Walk

Warrenville, IL

Sunday, September 27th, 2026

View details for race F3 Naperville 5K Run & Walk

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

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

Boo Island - 5K Charity Run/Walk

Blue Island, IL

Saturday, October 3rd, 2026

Trail

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

2026 Milwaukee Lakefront Marathon

Milwaukee, WI

Saturday, October 3rd, 2026

Marathon

View details for race 2026 Milwaukee Lakefront Marathon

Midwest Canine Obstacle Run

Benton Harbor, MI

Saturday, October 3rd, 2026

View details for race Midwest Canine Obstacle Run

Long Grove's Oktoberfest Half Marathon, 10K & 5K

Long Grove, IL

Saturday, October 3rd, 2026

Half

10K

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

Wisconsin Cheese Run

Muskego, WI

Saturday, October 3rd, 2026

View details for race Wisconsin Cheese Run

Angels Against Abuse 5K Walk/Run

Romeoville, IL

Saturday, October 3rd, 2026

View details for race Angels Against Abuse 5K Walk/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

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

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

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

JJC Foundation 5K Run/Walk

Joliet, IL

Sunday, October 4th, 2026

1 Mile

View details for race JJC Foundation 5K Run/Walk

The Milwaukee Beer Run 5k & .05k

Glendale, WI

Sunday, October 4th, 2026

Trail

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

Fire Zone 5k

Lockport, IL

Sunday, October 4th, 2026

Trail

View details for race Fire Zone 5k

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

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

Welcome Run 5K

Lansing, IL

Saturday, October 10th, 2026

View details for race Welcome Run 5K

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

Care4 Breast Cancer Hybrid 5K

Woodstock, IL

Saturday, October 10th, 2026

View details for race Care4 Breast Cancer Hybrid 5K

12th Annual Harvest Hustle 5K

Niles, IL

Saturday, October 10th, 2026

View details for race 12th Annual Harvest Hustle 5K

El Trote De Las Calacas

Elgin, IL

Saturday, October 10th, 2026

View details for race El Trote De Las Calacas

Fit 4 Fall 5K Run/Walk

St. Joseph, MI

Saturday, October 10th, 2026

View details for race Fit 4 Fall 5K Run/Walk

Nik's 7K Home Run & 1.5 Mile Walk at MercyHealt...

Loves Park, IL

Saturday, October 10th, 2026

1 Mile

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

Slicer Performing Arts Club (SPArC) 5K Run and ...

La Porte, IN

Sunday, October 11th, 2026

View details for race Slicer Performing Arts Club (SPArC) 5K Run and Walk

2026 Bank of America Chicago Marathon

Chicago, IL

Sunday, October 11th, 2026

Marathon

View details for race 2026 Bank of America Chicago Marathon

JAIMIE COX MEMORIAL RUN

Roscoe, IL

Saturday, October 17th, 2026

Trail

View details for race JAIMIE COX MEMORIAL RUN

Spooky Sprint - Milwaukee

Milwaukee, WI

Saturday, October 17th, 2026

1 Mile

10K

View details for race Spooky Sprint - Milwaukee

Run and Creep 5k

Benton Harbor, MI

Saturday, October 17th, 2026

View details for race Run and Creep 5k

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