Windy City Cycling Club (WCCC)

10/10/2026

09/22/2026

🚴‍♂️🏳️‍🌈 Join Plainfield’s inaugural P Ride with the Mayor! 🏳️‍🌈🚴‍♀️

Looking for another reason to get out and ride this fall? Windy City Cycling Club is excited to share a new community cycling event happening in Plainfield!

📅 Sunday, October 4, 2026
🕛 Noon
📍 Village Green | Downtown Plainfield, IL
🚲 Choose a 10-mile or 20-mile route

The P Ride with the Mayor is all about bringing people together through cycling while celebrating inclusion, community, healthy living, and the belief that everyone is welcome and everyone belongs. ❤️🧡💛💚💙💜

Organizers have extended a special invitation to Chicago’s LGBTQ+ cycling community. Whether you choose the 10- or 20-mile route, it’s a great opportunity to get some fall miles in, meet new people, and support an inclusive cycling community.

Grab your bike, bring a friend, and come ride with Plainfield! 🚲✨

08/10/2026

🚴‍♂️☀️ August miles before the storms! 🌩️

Our WCCC riders made the most of a beautiful August weekend, getting out on both Saturday and Sunday for some great miles, good roads, and even better company.

With storms rolling in, we knew we had to take advantage of the sunshine while we had it — and our riders delivered! 💪🚲

Nothing beats a summer weekend on two wheels with the WCCC crew. ❤️

08/04/2026

🌦️ Three days, countless miles, and one unforgettable weekend in Madison! 🚴‍♂️💙🌈

The forecast called for rain, but WCCC wasn’t about to let a little weather stand in the way of an amazing weekend on Wisconsin’s beautiful country roads.

The riding started Friday afternoon with a 30+ mile warm-up ride. Saturday brought options for everyone, with groups heading out for 30+ mile routes while others took on the epic 70+ mile adventure, including the climb through Blue Mounds to the highest point in Wisconsin. Every mile was rewarded with incredible scenery, great conversations, and plenty of shared encouragement along the way.

After a full day in the saddle, everyone came together in Madison for well-earned drinks, dinner, and plenty of stories from the road. Sunday wrapped up the weekend with a group brunch, one last ride, and the drive back to Chicago with tired legs and full hearts.

Another incredible Madison weekend is officially in the books. Thanks to everyone who joined the adventure and made it such a memorable trip. We can’t wait to do it all again next year!

07/26/2026

Sometimes you’ve got to mix up the Sunday route. 🚴🌤️

This week, WCCC rolled south instead of north, making our way to Pullman National Monument before crossing into Whiting, Indiana for one of the best recovery stops of the season: PierogiFest! 🥟

Nothing says “earned these miles” like a plate of pierogies and a little festival atmosphere before pointing our bikes back toward Chicago. Great roads, great company, and plenty of carbs to power the ride home.

Thanks to everyone who came out and made it another memorable Sunday on two wheels.

07/14/2026

Swap the saddle for a social hour! Whether you’re a long-time member or a newcomer looking to find your pace, join the Windy City Cycling Club for a mid-week meetup at one of the city’s most beloved local spots.
We’re taking over the patio at Max’s Place in Uptown. Known for its relaxed environment and inclusive, upbeat atmosphere, it’s the perfect place to talk gear, share upcoming ride plans, or just catch up with the WCCC crew over a drink.

• When: Thursday, July 23rd
• Time: 7:00 PM - 9:00 PM (Feel free to drop in whenever!)
• Where: Max’s Place | 4621 N Clark St, Chicago,
IL 60640
• Vibe: Casual, social, and bike-talk friendly

No kit required-just bring yourself and a love for the road. Whether you’ve been putting in the miles this summer or are just getting the bike out of storage, we can’t wait to see you there.

Note: This is a social-only event (no organized group ride to the venue), but we always encourage you to ride your bike if you’re local! 🚴

06/24/2026

🌧️ On rainy Wednesdays like this, what better time to look back at the great rides we enjoyed over the weekend!

Saturday brought plenty of sunshine as our casual group rolled south along the lakefront to Hyde Park, soaking up the beautiful weather, good conversations, and all the joy that comes with riding together. ☀️🚴

Others were back in the saddle on Sunday, sneaking in miles on the North Branch Trail before the rain moved in. No matter the route or pace, there was plenty of fun to be had and memories made with friends.

Looking for your next ride? Check us out on Meetup or Strava and come join us for the miles, the laughs, and the community. Everyone is welcome!

🚴‍♂️🌈☕️

06/14/2026

Mother Nature may have had other plans for Sunday’s ride, but Saturday delivered a perfect day on two wheels! 🚴‍♂️☀️🏳️‍🌈

A fantastic WCCC turnout headed south along the lakefront toward Hyde Park, enjoying great miles, great company, and celebrating Pride Month with fellow LGBTQ+ cyclists and allies. There’s something special about sharing the road, stories, laughter, and community with friends who make every ride feel welcoming and inclusive.

As an added bonus, riders got to take in the excitement of Chicago hosting the first-ever U.S. Red Bull Spin Off, where 39 teams raced custom tandem bicycles across a floating obstacle course on Lake Michigan. The creativity, costumes, and spectacular splashdowns made for an unforgettable scene!

While the rain washed out Sunday’s plans, Saturday was a reminder that the best rides are about more than the miles. They’re about community, friendship, visibility, and celebrating who we are, both on and off the bike.

Happy Pride Month from WCCC! 🏳️‍🌈🚴‍♀️🚴‍♂️

06/01/2026

Another fantastic weekend on two wheels with WCCC! 🚴‍♂️☀️

Saturday’s casual ride took us along the beautiful Lakefront Trail all the way down to Hyde Park, with plenty of sunshine, great company, and lake views that never get old.

Sunday’s training ride pointed north toward Northbrook, adding some solid miles and setting the stage for an incredible riding season ahead.

The highlights? Great weather, strong legs, endless conversations, excellent coffee, fresh pastries, and the kind of camaraderie that makes every mile more enjoyable.

Here’s to good friends, good rides, and many more miles ahead. 🚴‍♂️☕🥐

RoadCycling CyclingLife CoffeeRide WeekendMiles RideMore BikeChicago CyclingCommunity

05/05/2026

🚴‍♂️✨ Swap the saddle for a social hour! ✨🚴‍♂️

Whether you’re a long-time member or just looking to find your pace, join the Windy City Cycling Club for a mid-week meetup you won’t want to miss.

📍 Nobody’s Darling (Andersonville)
📅 May 14
⏰ 7–9 PM

Good vibes, great company, and one of the city’s most beloved neighborhood spots. Come unwind, connect, and maybe even plan your next ride.

All are welcome, so bring a friend and let’s make it a night. 🍻

CyclingComm