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Tag: chicago cycling events

Tailwind is Proud to Support NICA Illinois

Illinois Finally Has a NICA League!

For years, Illinois was one of the most cycling-passionate states in the country without its own National Interscholastic Cycling Association (NICA) league. That changed in September 2025, when NICA officially launched the Illinois Interscholastic Cycling League — its 33rd U.S.-based league.

At Tailwind Cycles, we couldn’t be more excited. As a bike shop rooted in Chicago’s Northwest Side, we’ve seen firsthand what cycling does for people: the confidence it builds, the communities it creates, and the doors it opens. Now, through our support of Illinois NICA, we’re helping bring those same benefits to the next generation of riders across the state.

What Is NICA?

The National Interscholastic Cycling Association is a nonprofit youth development organization that uses mountain biking to build strong minds, bodies, character, and communities. Founded in 2009 in Berkeley, California, NICA has grown into a nationwide network supporting over 25,000 young riders and 15,000 volunteer coaches annually across more than 30 leagues.

What sets NICA apart from most youth sports is its philosophy: there are no tryouts and no one sits on the bench. Every kid rides. Every kid trains with their team. The organization is guided by core values of fun, inclusivity, equity, respect, and community.

As NICA President Amanda Carey put it when announcing the Illinois league: “All kids deserve the type of sports opportunities and programs that NICA provides”.

The Illinois League

The Illinois Interscholastic Cycling League was founded in 2025 by League Director Micah Ariel-Rohr, with its first season of racing planned for Fall 2026.

The league is building on Illinois’s vibrant cycling culture and inclusive Midwestern ethos. Its leadership team brings deep roots in the Chicago cycling community, including experience with youth programs like Blackstone Bicycle Works, Chicago United cycling team, and the Wisconsin NICA League.

Chicago-based SRAM, a global leader in cycling components and a longtime NICA national partner, played a pivotal role in bringing the league to life, announcing a $25,000 match-giving campaign at launch to support the league’s early operations, outreach, and Girls Riding Together (GRiT) programming.

What Illinois NICA Offers Young Riders

Illinois NICA brings the full suite of NICA programming to the state, including:

  • Team-based mountain biking for middle and high school students, with trained volunteer coaches and a challenge-by-choice environment
  • Girls Riding Together (GRiT) — NICA’s focused effort to recruit and retain more girls and women in cycling
  • Teen Trail Corps — a stewardship program that encourages student-athletes to give back to the trails where they ride
  • NICA Adventure — programming that ties together mountain biking, team camaraderie, and time outdoors

The league season runs from July through October, with registration opening in spring and league-wide events — races, adventure rides, and more — beginning in the fall.

Why Tailwind Cycles Supports Illinois NICA

Since 2017, we’ve been helping riders across the city with expert service, bike fits, and a genuine love for the sport. We support Illinois NICA because we believe in what they’re building. When we see a kid come into the shop excited about a ride, or a parent asking about their first mountain bike, we know the spark that cycling can light. NICA gives that spark a home — a team, a coach, a community, and a reason to keep pedaling.

We’re especially proud to support a program that puts inclusivity at its core. Not every kid fits into traditional team sports. NICA meets them where they are and gives every rider a place to belong. That’s the kind of cycling community we want to help grow.

How You Can Get Involved

The Illinois league is actively forming teams and recruiting coaches and volunteers across the state. Here’s how you can help:

  • Student-athletes: Find a team near you and register through the NICA Pit Zone at illinoismtb.org
  • Adults: Sign up to coach or volunteer — all skill levels welcome
  • Everyone: Donate to the Illinois league at illinoismtb.org to help fund operations, outreach, and programming

And of course, if you or your young rider needs a bike, a tune-up, or advice on getting trail-ready, come see us at Tailwind Cycles — 3259 W Lawrence Ave, Chicago. We’re here to help you ride.


Tailwind Cycles is proud to support the Illinois Interscholastic Cycling League and the National Interscholastic Cycling Association’s mission to build strong minds, bodies, character, and communities through cycling.

MARCH 2026 CYCLING EVENTS IN CHICAGOLAND

Ullr, the Norse god of winter, hung up his crampons and stowed his toboggan for the year, which means the thaw is officially underway, and for Chicago cyclists that means one thing: it’s time to trade the indoor trainer for the open road. From the social miles of Wauconda to the brutal gravel grind of the “Hell of the Wind,” March is packed with opportunities to test your legs and fortitude. Whether you’re looking for a high-speed criterium or a muddy post-season cyclocross challenge, here are the key events hitting the Midwest calendar this month.

St. Patrick’s Day Ride — March 15

https://wheelmen.com/st_pats.asp

This fun, social road and general ride takes place in Wauconda, IL, celebrating St. Patrick’s Day with cyclists of all levels. The ride is a community favorite that embraces the seasonal transition into spring and leverages festive energy for a group outing.

Hell Of The Wind — March 28

https://www.bigrivergravel.com/about-1

Held in New Liberty, IA, Hell Of The Wind is a challenging gravel ride that pushes participants over variable terrain typical of early spring gravel seasons. Riders can expect rougher roads, wind exposure, and a strong testing ground for the upcoming cycling calendar.

Melting Mann — March 28

https://meltingmann.com

The Melting Mann event in Vandalia, MI is a spring gravel ride designed to shake off winter rust. It tests riders’ endurance across melting terrain and often muddy conditions as routes loosen with warmer temperatures approaching.

Autobahn Omnium — March 28 – 29

https://www.bikereg.com/autobahn-omnium

The Autobahn Omnium in Joliet, IL is a criterium racing event where riders compete in high-speed circuits around a closed course. As part of the spring racing calendar, this event attracts both local and competitive racers seeking fast laps and tactical competition.

Return to the Hills CX — March 29

https://www.bikereg.com/return-to-the-hills

Return to the Hills Cyclocross in Rockford, IL can be seen as the earliest cyclocross race of the season, or the latest race of last season, or just a thing of its own. Either way, It’s an off-road challenge that combines grass, mud, and technical obstacles. If you didn’t get enough cyclocross during the Chicago Cross Cup, here’s a second chance at glory.

Great Lakes Rando — March (Date TBD)

https://glr.greatlakesrando.org/stats/pages/myClub.xhtml

The Great Lakes Rando in Barrington, IL is a long-distance randonneuring event where cyclists ride extended courses at their own pace. With routes that test endurance and navigation skills, this ride embraces the tradition of unsupported, self-paced cycling.

There’re more events to come, keep checking the site for updates!

2025 Cyclocross Service Package

Mud happens. We handle it. Gear up for the Chicago Cross Cup (CCC) with Tailwind’s all-in service package designed to keep your race bike fast, quiet, and ready every weekend.

What’s included for $270

  • Pre-season full tune-up to dial shifting, braking, and tire clearance.
  • One bike wash + lube between every race (that’s 9 clean/relube services across the series, plus mechanical tweaks).
  • Race-day mechanical support at the Tailwind tent for those last-minute adjustments.
  • Optional bike transport to the race—skip the rack and focus on your start.
  • Racing with a backup in the pit? We’ll act as your pit crew during the race.

Extra perks

  • 15% off parts for your race bike.
  • 20% off tubular gluing.
  • If a race is canceled, you’ll get shop credit for a clean & lube.

Ready to roll? Bring your bike in for the pre-season tune, lock in your spot for all 9 CCC rounds, and let us sweat the maintenance while you chase the holeshot.

Call or stop by Tailwind Cycles to sign up today.

Interested in Other Races?

In addition to the Cross Cup, the other big racing series in the area is the Wisconsin CX series.

For other rides and races in Chicagoland, check out the Northern Illinois Cycling Index.

August Bike Rides and Races in Chicagoland 

Below we highlighted some fun rides or races within a two-hour drive from Chicago (in light traffic, bleh) along with a comprehensive list of events in the table at the bottom. Thanks to Cycling Index – Northern Illinois Cycling for assembling this data.  

Looking for a bike shop near you that can get your bike ready for any of these events? Talk to the Tailwind crew to get your wheels in shape (round, ideally) or hit us up for fitting.  

If you’re looking for a regular weekly group ride, Tailwind sponsors the Half Acre Wednesday night group ride. It’s roughly 20 miles from Winnemac Park to the Half Acre brewery – and there’s a slow group or a fast group.

Highlighted Rides in Chicagoland

Annual Velodrome 4k Time Trial

  • Date: Sunday, August 9, 2025 
  • Type: Time trial – velodrome 
  • Location: Northbrook, IL 
  • Details & registration:https://www.wiilcycle.org/event/2nd-annual-velodrome-4k-tt/

Little Apple Gravel (20k-40k) Time Trial

  • Date: Sunday, August 10, 2025 
  • Type: Gravel TT 
  • Location: Manhattan, IL 
  • Details & registration:https://www.bikereg.com/littleapple

Palos Meltdown CAMBR 

  • Date: Sunday, August 10, 2025 
  • Type: MTB Race 
  • Location: Palos MTB trails, IL 
  • Details & registration: https://cambr.org/news_manager.php?page=24504

Tri-State Tour Chicago Century

  • Date: Sunday, August 23, 2025 
  • Type: Non-competitive entury ride (also non-century option) 
  • Route: Whiting, IN → Kenosha, WI 
  • Details & registration:Bicycle Illinois – Illinois’ Bicycle Touring Company

Return to Cherry Valley 20k Time Trial

  • Date: Sunday, August 24, 2025 
  • Type: Time trial (20k) 
  • Location: Cherry Valley, IL 
  • Details & registration:https://www.wiilcycle.org/event/return-to-cherry-valley-20k-tt/

Relay Cross Chicago

  • Date: August (date TBD), 2025 
  • Type: Cyclocross relay race 
  • Location: Chicago, IL 
  • Details & registration:Relay Cross – xXx Racing – Athletico

Chicago Triathlon

  • Date: August 23-24, 2025 
  • Type: Triathlon (includes cycling) 
  • Location: Chicago, IL 
  • Details & registration:Chicago Triathlon

Bike the Drive

  • Date: Sunday, August 31, 2025 – 6:30 AM start 
  • Type: Car-free city ride along Lake Shore Drive 
  • Location: Grant Park (Butler Field), Chicago 
  • Official site & registration: Active Transportation Alliance event info REGISTER – Bike the Drive

Event Summary Table

EventLocationDateType
CowaLUNGaGurnee, IL 8/2/2025 Road/General 
Bryce Master 19k TTHarvard, IL 8/2/2025 TT (Time Trial) 
Night Owl Bike RideCrystal Lake, IL 8/2/2025 Road/General 
Illinois Road Race ChampionshipSt. Anne, IL 8/3/2025 Road/General 
Little AppleManhattan, IL 8/3/2025 Gravel 
Naperville Sprint TriathlonNaperville, IL 8/3/2025 Triathlon (Tri) 
New Glarus Road RaceNew Glarus, WI August 2025 Road/General 
Annual Velodrome 4k TTNorthbrook, IL 8/9/2025 TT (Time Trial) 
Palos MeltdownPalos Park, IL 8/10/2025 Mountain/Fat Bike 
Double Bong 20–40 km TTKansasville, WI 8/10/2025 TT (Time Trial) 
Rotary RideNaperville, IL August 2025 Road/General 
Ride Like An EgyptianDeKalb, IL August 2025 Road/General 
Fast FittyCharlotte, MI 8/16/2025 Gravel 
core4Iowa City, IA 8/16/2025 Gravel 
10 Mile TT National ChampionshipMaple Park, IL 8/17/2025 TT (Time Trial) 
Race the LakeFond du Lac, WI August 2025 Road/General 
Ride Across WisconsinSouthern, WI August 2025 Road/General 
The Coon Fork 40Augusta, WI 8/23/2025 Gravel 
Return to Cherry Valley 20k Time TrialCherry Valley, IL 8/24/2025 TT (Time Trial) 
Tri-State TourTri-State (IL/WI/IN) August 2025 Road/General 
TreadfestLake Geneva, WI August 2025 Mountain/Fat Bike 
Relay CrossChicago, IL August 2025 Cyclocross 
Chicago TriathlonChicago, IL August 2025 Triathlon (Tri) 
Fall Fling Stage 1Wood Dale, IL 8/30/2025 Criterium 
Fall Fling Stage 2Wood Dale, IL 8/31/2025 Criterium 

Chicago Bike Races and Rides in May

Here is a list of bike races in the Chicago area, plus things to do on a bike for May of 2025. Events are divided into races for competitive cycling, and rides for social outings or non-competitive endurance events (like brevets).

If you’re looking for a regular group ride, check out Half Acre Cycling’s group ride finder.

Races:

May 3: 1904 Gravel Race – Illinois City, IL

May 4: Harvard 33.3k Time Trial – Harvard, IL

May 6: Labagh Woods Ladies’ Night Crits – Chicago, IL

May 13: Labagh Woods Practice Crits – Chicago, IL

May 15: Thursday Night Track Racing – Northbrook, IL

May 18: Kankakee 20k Time Trial – Kankakee, IL

May 24: ABD Memorial Day Weekend Omnium #1 – Wood Dale, IL

May 25: ABD MDW Omnium #3 – Wood Dale, IL

May 25: Kane County Ten Mile Time Trial – Maple Park, IL

Rides

May 3: The Chicago Tweed Ride – Oak Park, IL

May 3: Barrington Boomerang 200k – Barrington, IL

May 4: Pastry-Bike-Pastry – North Aurora, IL

May 17: Pedalpalooza – Crystal Lake, IL

May 17: Chicago-Milwaukee-Chicago300k – Chicago, IL

May 18: Everybody Rides – St. Charles, IL

May 24: Blackhawk Country Roads – Rockford, IL

May 25: McHenry County Century – Lake in the Hills, IL

May 30: Chicago Critical Mass – Chicago, IL

May 31: Aurora City of Lights 400k – Aurora, IL

Pic from The Garden, Chicago’s north side bike jumping park.


/TAILWINDCYCLES

Tailwind Cycles is a full-service bike shop located in Albany Park, Chicago offering in-shop and mobile bike repair, tune-ups, and bike fitting.


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