2 cycling events in Cook County, Illinois
From big races to Saturday morning group runs—find cycling events and connect with the local endurance sports community.
Cook County
2 events in Cook County-
Sat, May 02, 2026 at 9:00 AMSee full details
The Universal Sole Spring Trail Challenge
THREE RAVINES COURSE - BRING YOUR YAKTRAX
Athletes get to choose 3.1 or 5.4 mile race course
MAY 2, 2026 @ 9AM
Trail running has always been in our USOLE DNA! We were the first running store in Chicago to bring trail racing to the Chicago running community. These trail races are great courses for folks wanting to get off the roads and enjoy some of our beautiful trails, but not have to be an expert trail runner to get to the finish. Our trail races are very laid back and great fun for the entire family, making it fun & easy for all! The USOLE Trail Challenge is great for people of all ages and all abilities looking to change up the running routine and get “off” the roads!
Trail Race Location:
We will be headed back to Wolf Road Woods, part of the Palos Trail System to tackle a the legendary Three Ravines Course! We can't wait to show you some new trail and bring this course into the USOLE Trail family repertoire of fantastic trail courses. This course will have a great mix of double & single track along with undulating terrain in the beautiful Wolf Road Woods! It may have a small hill or two to climb as well, but fun will always be had! USOLE Trail Challenge races are a great way to see the trails, get your long run and enjoy camaraderie with your trail running friends!
Race Details:
Spring Trail Challenge Pricing:
February 1 - February 28 - $40.00
March 1 - March 31 - $45.00
April 1 - Until Race Day - $55.00
No exchanges or refunds
The Goods:
Every registered runner will get a cool USOLE Premium Trail Giveaway. Stay tuned as we will announce soon!
Brews & Craft Brews for all to enjoy post race.
Killer raffle
Course will be trail & off road with crushed limestone, dirt, rocks, & roots...and maybe some mud. Fun is the name of the game!
If you have Yaktrax or a clip on traction device, you may want to bring them for extra traction as spring trails can have a bit of mud.
Race will begin promptly @ 9:00am. Race day pickup & registration will begin @ 8:00am!
Weather Issues: In the case of inclement weather, the only time we will delay a race or consider any action is in the presence of lightning. All other weather (rain, snow, tons of snow, tons of rain, etc) we will run the race. After all, this is trail running and some inclement weather makes it that much more fun!
Water at the Start/finish line. Due to Cook County Forest Preserve regulations, we are not allowed to have any aid station in the trails. We will have an aid station at the start/finish line and at the halfway point so you can fill up any bottles or get nutrition at those points. It is highly recommended you come with your own bottle, hydration pack and personal choice of nutrition supplements.
-Granola Bars and bananas will be at the finish for all athletes.
-Refreshing brews will be given to all runners after the race.
-Race day gear check will be at Universal. Sole Tents/registration tables
-Parking Info: Plenty of parking in the forest preserve parking lots!
Directions to race site:(Wolf Road Woods) - Coming from the north, take I-55 to Exit 279A, southbound La Grange Road. Drive south for roughly 2 miles and exit south onto Archer Avenue to 95th. Left on 95th and take that to the split and veer a soft right to the Forest Preserve Entrance/Wolf Road. Follow Wolf Road all the way to the end, go right and to the USOLE Race Site @ Wolf Road Woods - Grove #2.
Awards:
-Overall winners for Female, Male & Non-Binary will receive custom award tiles for the 3.1 Mile & 5.4 Mile Races.
-Full Age Group Awards for 5.4 mile race - Top three in each age group (Female, Male & Non-Binary): 0-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70-79, 80+
-Age Group Awards for 3.1 mile race - Age group winners only (Female, Male & Non-Binary): 0-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70-79, 80+
-Post race raffle with great prizes from Universal Sole & all of our sponsors to be held at our post race party on-site!
Packet Pick-up & Race Day Registration:
*Packet pick-up will be available on race morning starting @ 8:00am from the USOLE Tents/tables. We will also have race morning registration for folks (it will be at a higher price, so be sure you pre-register before)
Post Race - Craft Brews & Fun!
Once the races are over, we will have local craft brews for everyone! We will have some other goodies for folks as well to enjoy, but let's run, have some fun and enjoy some fine craft brew styles from our USOLE Trail Challenge sponsors! We will also have a killer raffle for all runners with some really cool prizes from all of our sponsors. Come for the (trail) run, stay for the fun!
BRING OLD RUNNING SHOES OUT TO THE RACE TO RECYCLE!
Reduce Waste Chicago -- They help Chicagoan's reduce their waste output through reusing, repairing and recycling. They work with organizations across the city to host Reuse & Recycle Pop-Up events, where residents can drop off materials from our accepted items list that are not accepted by the city’s Blue Cart program. RWC distributes items to other organizations, local nonprofits, artists groups and recycling companies – all of which improves landfill diversion. Reduce Waste Chicago will be out at the USOLE Trail Challenge Races accepting running shoes for recycling. For more information, click here.
Volunteer Information: Please email Universal Sole ([email protected]) and let us know if you would like to take part by volunteering.
Strollers & Dogs: Strollers and leashed dogs are allowed, we ask that you start in the last start time corral.
*Please note: There are no refunds, exchanges or person to person entry transfers for this event. Discount codes can't be used on race day/night registration (best is to sign up pre-event on-line here).
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Sat, Jun 27, 2026 at 9:00 AMSee full details
The Universal Sole Summer Trail Challenge
THREE DISTANCES to Choose!
3 Miles-> 6->Miles-> 9 Miles
June 27, 2026 @ 9AM
Trail running has always been in our USOLE DNA! We were the first running store in Chicago to bring trail racing to the Chicago running community. These trail races are great courses for folks wanting to get off the roads and enjoy some of our beautiful trails, but not have to be an expert trail runner to get to the finish. Our trail races are very laid back and great fun for the entire family, making it fun & easy for all! The USOLE Trail Challenge is great for people of all ages and all abilities looking to change up the running routine and get “off” the roads!
Trail Race Location:
We will be headed to Wolf Road Woods, part of the Palos Trail System to tackle our classic USOLE 3 mile course! This course will have a great mix of double & single track along with undulating terrain in the beautiful Wolf Road Woods! It may have a small hill or two to climb as well, but fun will always be had! You have three options to choose...One loop, Two loops or Three loops! You choose your distance! USOLE Trail Challenge races are a great way to see the trails, get a trail run in and enjoy camaraderie with your trail running friends!
Race Details:USOLE Summer Trail Challenge Registration Pricing:
Opening Price until February 28 - $40.00
March 1 - April 30 - $45.00
May 1 - May 31 - $50.00
June 1 - Race Day - $55.00
No exchanges or refunds
The Goods:
Everyone receives a USOLE Trail Challenge premium giveaway
Brews for all post race!
USOLE camaraderie and fun as always!
Courses will be trail & off road with crushed limestone, dirt, rocks, & roots...and maybe some mud. Fun is the name of the game!
Races will begin promptly @ 9:00am. Race day pickup & registration will begin @ 8:00am.
Weather Issues: In the case of inclement weather, the only time we will delay a race or consider any action is in the presence of lightening. All other weather (rain, snow, tons of snow, tons of rain, etc) we will run the race. After all, this is trail running and some inclement weather makes it that much more fun!
Water will be at the Start/finish line. Due to Cook County Forest Preserve regulations, we are not allowed to have any aid station in the trails. Runners running the 6 or 9 mile will have access to water before heading out back out on the second & third three mile loops. It is recommended to carry a hand held bottle or a hydration belt if you need on-course hydration. Bottles can be filled at start/finish line as well as at the split aid station.
-Granola Bars & bananas will be at the finish.
-Race day gear check will be at the Universal Sole Tents
-Parking Info: Plenty of parking in the forest preserve parking lots!
Directions to race sites (see map and address below):
(Wolf Road Woods) - Coming from the north, take I-55 to Exit 279A, southbound La Grange Road. Drive south for roughly 2 miles and exit south onto Archer Avenue.
Awards:
-Overall Male & Female will receive custom tile awards for 9 mile race.
-Full Age Group Awards for the 9 MILE TRAIL RACE ONLY, Top three in each age group: 0-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70-79, 80+
-The 3 & 6 Mile will have age group winner awards only.
-Post race raffle with great prizes from Universal Sole & all of our sponsors to be held at our post race party on-site!
-Packet Pick-up & Race Day Registration:All packets/numbers can be picked race morning on-site @ Wolf Road Woods (Palos) from 8:00am until 8:45am @ The USOLE Tents.
If you would like to register for the race, you may do so on-site at the USOLE Tents from 8am - 8:45am race morning. We highly recommend registering pre-race, but can take walk-ups as well.
Post Race Brews & Fun!
Once the races are over, craft brews for everyone (along with an N.A. alternative as well)! We will have some other goodies for folks as well to enjoy, but let's run, have some fun and enjoy some beer! Once again we will have some brews from our sponsors, Bitter Pops & Goose Island Beer Company for all folks to enjoy and sip while celebrating your accomplishment! Come on out, enjoy some great summer trail running, great craft brews and tons of camaraderie!
BRING OLD RUNNING SHOES OUT TO THE RACE TO RECYCLE!
Reduce Waste Chicago is a nonprofit organization that empowers residents to address climate change through waste reduction on a personal, producer, and policy level. They host Reuse & Recycling Pop-Up events across the city, where they collect a selection of items that can be reused, repurposed, or are difficult to recycle. Reduce Waste Chicago will be out at USOLE races accepting running shoes for recycling (athletic shoes only; please no packaging, bags, boxes, etc.) For more information, click here.
Want To Volunteer? Please email: [email protected]
Please note: No refunds or exchanges for this event