Run, walk, and toast your accomplishment with a pour of wine at this delightful 5k event.

• Fun
• Competitive
• Quirky

Sat, Apr 11, 2026, 8:00 AM CDT·5K·Chicago, IL

EasygoingRUN

Course · Flat · Timed race

A delightfully quirky, donut-themed race for all ages and paces, offering a sweet reward at the finish line.

• Fun
• Quirky

Run a scenic 5K with your dog (or without!) to support Chicagoland Lab Rescue, complete with unique dog-themed swag and treats.

• Fun
• Scenic
• Competitive
• Quirky

Run or walk a scenic 5K through Eckert's Belleville Farm, then celebrate with wine and a medal that's also a wine stopper.

• Fun
• Scenic
• Competitive
• Quirky

Run or walk as a superhero to support Braveheart CAC, raising awareness for child abuse, sexual assault, and mental health in the community.

• Fun
• Competitive
• Quirky
• For a Cause

A supportive, coffee-themed run in Chicago/Evanston where every post-race mile you log helps charity.

• Fun
• Quirky
• For a Cause

Run a beautiful Chicago course and earn a sweet reward: fresh donuts at the finish line, all while supporting charity.

• Fun
• Scenic
• Quirky
• For a Cause

Get ready for a totally rad 80s throwback at this community 5k and 1-mile fun run, complete with neon and a post-race party.

• Fun
• Quirky
• Festive

Run or walk a 5K, then celebrate with a pour of award-winning wine at Cooper's Hawk Winery. A perfect blend of fitness and fun.

• Fun
• Quirky

Get ready to be doused in color at this untimed 5K, a joyful community event supporting Orient's 4th of July Celebration.

• Fun
• Quirky
• Festive
• For a Cause

Run, dance, and celebrate at this 5K music festival under the lights, supporting Stand Up To Cancer.

• Fun
• Quirky
• Festive
• For a Cause

Unleash your inner superhero for a great cause at this inclusive, stress-free run, celebrating every mile with a charity donation.

• Fun
• Quirky
• For a Cause

A sweet 5k run or walk through Eckert's Belleville Farm, complete with a donut theme and a delicious treat at the finish.

• Fun
• Scenic
• Competitive
• Quirky

Run a 5K with Lincoln, then celebrate at a lively street festival featuring local food, drinks, and live music in downtown Petersburg.

• Fun
• Competitive
• Quirky
• Festive

A uniquely relaxed run where slow is celebrated, competition is optional, and every mile helps a cause.

• Fun
• Quirky
• For a Cause

Indulge your sweet tooth and your love for running at this deliciously fun, stress-free event with a charitable twist. All paces welcome.

• Fun
• Quirky
• For a Cause

A charming, dog-themed 5k in Aurora, featuring scenic park views and special treats for both human and furry friends.

• Fun
• Scenic
• Quirky

Indulge in a sweet finish at this supportive, community-focused run, where donuts await you after a beautiful course.

• Fun
• Quirky
• For a Cause

Run for the carbs and stay for the bagels at this relaxed, community-focused event that supports charity with every mile.

• Fun
• Quirky
• For a Cause

Slow is the new fast at this chill, supportive run where every pace is celebrated and good vibes lead the way.

• Fun
• Quirky
• For a Cause

Honor 9/11 heroes and support our service members and first responders in this unique 5K, featuring an optional GORUCK rucking challenge.

• Quirky
• For a Cause

Indulge your sweet tooth on National Chocolate Day with a fun, stress-free run that supports your goals and gives back to charity.

• Fun
• Quirky
• Festive
• For a Cause

Run a beautiful course and earn your donuts at the finish line, all while supporting charity in a friendly, stress-free group setting.

• Fun
• Quirky
• For a Cause

A Halloween-themed 5K run or walk through Busse Woods, capped off with a celebratory wine pour and unique finisher swag.

• Fun
• Competitive
• Quirky
• Festive