NICA: Wisconsin Interscholastic Cycling League

See schedule & locations on Trek's website

The WI League is committed to providing a positive co-ed cycling experience for middle and high school aged students of all cycling levels using coaching methods founded in our FIERC values of Fun, Inclusivity, Equity, Respect and Community. Each WI League season includes programs from all facets of NICA:  Adventure, GRiT, Teen Trail Corp and a fall race series.  There is something for everyone!

WORS: Wisconsin Off Road Series

See schedule & locations at the link below

Entering its 32nd year, the Wisconsin Off Road Series is back again for another season of the country’s premier mountain bike racing experience. WORS offers riders of all backgrounds a competitive, fun, and family-friendly environment to test their skills on Wisconsin’s finest trails. WORS is an awesome place to make the life-changing leap into racing. Beginners will find a welcoming climate with several race options, including a one-lap “Try-it-out” option to see if you like it.

Bike Out Negativity

May 17th - Chicago, IL

Chicagoland... The 5th annual "Bike Out Negativity" is on for Saturday, May 18th! This event is FREE & registration is open to all. Boxing Out Negativity will be hosting a pre-ride party for all featuring local community organizations from 12pm-3pm, along with giveaways for West Side youth. At 3pm, the 6-mile fun ride will kick off for all! 

UPAF Ride for the Arts

June 1st - Milwaukee, WI

UPAF's iconic, family-friendly ride, is a must for any cyclist! On this completely closed course, you'll get amazing views as you ride over the Hoan Bridge & down Lincoln Memorial Dr. Riders looking for a leisurely ride can enjoy the Arts Path around Lake Shore State Park. All proceeds benefit the United Performing Arts Fund!

Wisconsin Bike Week

June 1st - June 8th

Each year, the Wisconsin Bike Fed coordinates with its members in communities across the state to organize fun local cycling events during Wisconsin Bike Week. From Commuter Stations to community rides, workshops, and even overnight camping trips, Wisconsin Bike Week is your chance for anyone to promote the best of their community by bike.

Green Lake 100

June 7th - Green Lake, WI

Join us for the beautiful Green Lake 100 Metric Century Bike Ride on Saturday, June 7, 2025! If bicyclists are looking for a challenging, yet fun ride featuring numerous routes of scenic beauty throughout the area, they need to look no further than the 8th annual Green Lake 100.  New this year, there will be three routes for you to choose from; 23 (37 km), 40 (64 km), and 62 (100 km) taking you through Green Lake County’s vibrant communities of Green Lake, Princeton, & Berlin. 10% proceeds of this ride will be donated to Green Lake Greenways.

Trek 100

June 7th - Waterloo, WI

The Trek 100 began as a humble charity bike ride to raise funds for childhood cancer and related blood disorders research. Over the last three decades, it's grown into something so much bigger. Since 1990, Trek 100 has raised over $22 million for the MACC Fund — and on June 7, we'll gather at Trek's global headquarters once again to ride, party, and support this crucial cause.

Tour of America's Dairyland (ToAD)

See schedule & locations at the link below

Tour of America’s Dairyland (ToAD) is the largest competitive road cycling series in the U.S. ToAD's 11-day criterium race series offers high-level, inclusive bike racing through vibrant Wisconsin communities. With fast and fun courses, energetic crowds, professional race production, and welcoming host communities, ToAD offers a uniquely immersive experience for racers and spectators alike. See you in June & be sure to make it to our ToAD Faterium on Thursday, June 19th in Bay View!

Fat Tire Tour of Milwaukee

June 14th - Milwaukee, WI

Drawing nearly 500 attendees each year, the Fat Tire Tour of Milwaukee is the oldest and most historic group ride in the greater Milwaukee area. With nearly 40 years under its “tires,” this annual movie-themed group ride attracts and unites young bucks and old dogs alike over a common love of bikes and beer. The FTTM is a casual paced ride covering 15-25 miles over a 6-7 hour span. Not only does the route change, but it’s a surprise until the morning of. 

Horribly Hilly Hundreds

June 14th - Mount Horeb, WI

With up to 10,000 feet of elevation gain, the Horribly Hilly Hundreds presents one of the Midwest’s toughest challenges for the serious cyclist. Nearly 1,000 riders participate in this one-day challenge ride that serves as an important fundraiser for Friends of Blue Mound State Park. Join the ranks of an inspired community of riders for the premier cycling event in the Badger State and beyond.

Bike MS: Tour de Farms

June 21st-22nd - Maple Park, IL

Enjoy midwestern charm – complete with minimal hills and long stretches of farmland – as you cycle through charming Kane County, Illinois. Bike MS: Tour De Farms is a two-day ride with fully supported routes. Surrounded by rural and scenic roads, you’ll be starting and finishing at Tour De Farms new venue, Kuipers Family Farm. 

Ride Across Wisconsin

July 12th - Eau Claire, WI

Scenic Shore 150

July 26-27th - Mequon, WI to Sturgeon Bay, WI

The beautiful shoreline of Lake Michigan is the picturesque setting for a weekend of riding 150 miles for a cure! Start in Mequon & pedal your way up to Sturgeon Bay in 2-days. One of Wisconsin's most popular rides, Scenic Shore 150 is the largest locally organized and supported event for the LLS. You don't want to miss this one! 

CowaLUNGa

August 2nd-3rd - Gurnee Mills, IL

The CowaLUNGa routes have been expertly designed using safe, scenic roads with limited traffic. You’ll experience just the right combination of hills and flats to challenge the new rider and keep the experienced cyclist engaged. It’s the view from your saddle that makes the tour so enjoyable. From farms and lakes to small country towns, there is plenty to see. Ride at your own pace, enjoy the tastes of Wisconsin (lunch each day is on your own), and keep an eye out for those cows!

Bike to the Beat

August 2nd - Appleton, WI

Bike to the Beat is a family-friendly bike ride for riders of all ages and skill levels. It’s a day filled with fun, comradery, live music, and a wide variety of free food, beer, and other beverages. And when we say it’s an event for all ages and skill levels, we mean it, thanks to a pair of starting locations (De Pere and Combined Locks) and multiple routes to choose from ranging from 7 miles all the way up to 57 miles.

MS 150: Best Dam Bike Tour

August 2nd-3rd - Baraboo, WI

This year’s ride will have you cycling through rural Wisconsin roads with spectacular views! Enjoy a fully supported two-day event that includes a blowout party on Saturday night with an amazing evening program. Bike MS: Best Dam Bike Tour is the best way to stay connected with your local cycling community and bring everyone together to reach our ultimate goal — a world free of MS.

Ride to the Barns

August 9th - Hartford, WI

Please join us for the 17th annual, 2025 Ride to the Barns - a benefit for farmland conservation in Lake Country! There are three different routes to choose: 30, 45 and 60 miles - with rest stops featuring local farms where only locally-sourced food is served! After the ride, join us for our post-ride party featuring live music, local beer, and a full buffet lunch!

TriMyBest

August 10th - Kenosha, WI

This is a ‘swim/bike/run’ event for children (5 & up) and young adults with developmental disabilities including Autism, Cerebral Palsy, Muscular Dystrophy, global delays, etc. ALL abilities are welcome, including those that may require the use of flotation devices, adapted bikes, walkers, power wheelchairs, and other assistive devices. All athletes will be paired up with volunteers to encourage, assist, and ensure safety.

Street Love Ride

August 16th - Chicago, IL

One City. One Ride. Street Love Ride. Meet in the boulevard across from St. Agatha Church, 3147 W. Douglas Blvd., Chicago, IL for a community expo (6pm-8pm) with music, snacks, and activities, followed by the Street Love Ride starting at 8pm - an approx. 9 mile "slow roll" bicycle ride through Chicago's West side.

Race the Lake

August 17th - Fond du Lac, WI

This is a stunning  timed bike ride around Lake Winnebago going  through 3 counties and many cities. The major intersections are controlled by police officers allowing the bikes to go first Every two miles and turns are highly visibly marked. You have 8 hours finish; about a 12.5 mph. Will you Race the Lake?

Bike the Drive

August 31st - Chicago, IL

Grab your bike and head on down to Lake Shore Drive... that's right! You get to ride your bike on a traffic-free Lake Shore Drive in Chicago! Fifth Third Bike the Drive is a fundraiser for the Active Transportation Alliance. Active Trans is a non-profit advocacy organization working to improve conditions for walking, biking, and public transit throughout Chicagoland.

Outdoorsy Tri MKE

DATE TBD - Milwaukee, WI

Come join us for our 3rd non-competitive, triathlon-based event! We'll walk from Yellow Wood to Wheel & Sprocket’s Fox Point location & bike to Milwaukee Kayak Company for a fun trip on the Milwaukee River. Post-party at a secret location! This was a sold out event in 2023 & 2024 - and we can't wait to bring it back this summer. Registration coming soon.

Ride on the Wild Side

September 14th - Milwaukee, WI

It’s the one time of year you can ride your bike inside the Milwaukee County Zoo. Take part in the kids’ 2.5-mile ride or challenge yourself to the 10-, 17- or 27-mile route. All riders get a long-sleeved T-shirt, breakfast, lunch and a day at the Zoo.

Chris' Slow Roll

September 21st - Milwaukee, WI

Slow Roll with us at our FREE, family-friendly, 10-mile bike ride along the scenic lakefront. We'll start the 10thth Annual Ride at the War Memorial in downtown Milwaukee, we’ll ride north on Lincoln Memorial Dr. up to Shorewood, then snake back on the Oak Leaf Trail where we’ll end where we started! Gathering for a party at the Beer Garden at the War Memorial, provided by Kegel’s Inn!

North Shore Century

September 21st - Evanston, IL

Evanston Bicycle Club presents the 40th annual North Shore Century -- Chicagoland’s premiere cycling event.  You’ll ride through beautiful neighborhoods, view unique architectural treasures, pedal down tree-lined streets and feel the refreshing breezes of Lake Michigan while enjoying the flat to rolling countryside between Chicago and Wisconsin. Our new home base is the Lakeview Center at 800 Gillson Park Drive in Wilmette. 

Fall Color Festival

September 27th - Kettle Moraine State Forest, WI

Join us on Saturday, Sept 27th for a full day of heart-pounding, side-aching, gear-grinding, mountain bike excitement for the entire family! Help raise funds to build and maintain fun, sustainable, high-quality, single-track mountain bike trails in the Southern Unit of the Kettle Moraine State Forest.

Tour de Chequamegon

October 3-5th - Cable, WI

Ride the scenic gravel roads of Wisconsin’s Northwoods this fall with Wheel & Sprocket on the 10th Annual Tour de Chequamegon! Roll through the dense forest, uplands and along remote lakes in the Chequamegon National Forest. Join the bikepacking ride that literally put Wisconsin gravel on the map! Limited to 55 spots - registration is OPEN!

Hugh Jass Fat Bike Series

Winter 2025-2026

More information coming soon...

Interested in Hosting a Group Ride?

Are you interested in hosting a Group Ride? Any and all Wheel & Sprocket Locations would love to be your meetup spot! 

Fill out the form below, tell us a little bit about your ride, and we'll be in touch to help create an environment for you to host a group ride!