Photo: Todd Ryburn from Bloomington, IL, United States · CC BY 2.0
Bloomington · United States

Cycling & running events in Bloomington, 2026

181events this year

181 races within 80 km of Bloomington

Road, trail, gravel, MTB — you name it, we've got it. Find something worth telling your friends about.

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153Running
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13Other
Top events

A few races to know in Bloomington

We all need a goal — why not think big? Pick one and start training for it. Already happened this year? Find some practice races to build toward next year's edition.
Run·Road
Bloomington

Paint the Town Pink

Paint the Town Pink is a breast cancer awareness walk and community event held at Switchyard Park in Bloomington, Indiana. The event originated from a Breast Cancer Awareness walk started by Melody Martin over 25 years ago, and it benefits education, patient support services, survivors, and earlier breast cancer detection. The walk utilizes Switchyard Park's half-mile or one-mile trail, designed for participation rather than speed. Cancer Support Community South Central Indiana organizes it with partners such as Bloomington Parks and Recreation, IU Health, and the IU School of Medicine. The day features a Breast Cancer Survivor Ceremony, educational materials, a resource fair, and food trucks. Locally, businesses can participate by displaying pink window paint, ribbons, awareness messages, clings, or digital toolkit items.

Road
Run·Trail
Bloomington

Bloomington Montessori Fall Fun Run 5K Trail Race and Family Fun Run

The Bloomington Montessori Fall Fun Run is a 5K trail race in Bloomington, Indiana, hosted at Fowler Pumpkin Patch prior to the school's Fall Fest. It originated as a family activity for Bloomington Montessori School and has expanded to include the public, with shorter one- or 1.5-mile family fun run routes commencing shortly after the 5K. The event maintains a school-community atmosphere: check-in begins in the morning, ABTiming handles the race timing, and volunteers assist with check-in and course guidance. Participants receive snacks and water upon finishing, the top three 5K runners are awarded medals, and all participants receive a T-shirt designed by a BMS parent. The run also functions as a fundraiser for the school, with past contributions supporting costs such as AEDs.

Trail
Run·Road
Bloomington

Monster Dash

The Monster Dash is a morning 5K at Weber High School, starting at 9 a.m. on the practice field and finishing on the school track. It is a Halloween-themed community race with a 1-mile kids run/walk afterward. All proceeds go to Weber High's Quarters and Cans fundraiser, with a large donation also going to Primary Children's Hospital. The 5K follows a loop from Weber High up 500 West, along Canal Road, down Washington, and back to the school. The opening section climbs, then the rest is flat or downhill. Runners receive hand-timed results, an aid station, and awards for the top male and female finishers. Costume prizes are also awarded. The Kids Trick or Treat Mile starts after the 5K, and children should bring a bag, bucket, pail, or pillowcase for collecting treats.

Road
About cycling & running in Bloomington

Bloomington Base Miles

Running: Locals run the B-Line when they want easy downtown miles without cars. The B-Line runs 1 mile through Bloomington and connects with the two-mile Bloomington Rail Trail for a longer out-and-back. You get 8 miles when you link it cleanly. 8 paved miles mix small hills and recovery flats. Fleet Feet Bloomington hosts Monday 6:00 pm runs. InRunCo Group Run adds campus miles. Strawberry Shortcake 5K, B-Town Turkey Trot, and Monster Dash keep the calendar honest.

Cycling: Locals ride easy on the B-Line Trail and around Indiana University, then point the bike toward Brown County, Lake Monroe, Morgan-Monroe State Forest, and Yellowwood when they want real climbing. Bloomington Bicycle Club is the main club, and its Wednesday gravel rides are where a lot of base miles happen. Wednesday Worlds rolls from Sample Gates at 6:00 pm with a chill start and a competitive, fast paced racing portion. Lampkins Ridge rd to Friendship rd to Kent rd gives riders about 25-30 miles depending on the start. The climb is 1 km with 1,076 m of elevation.

Season: Spring is the sweet spot because everything is in bloom and the greenways feel easy to stack. Summer puts Bloomington into the mid-to-high 90s, so locals shift runs to the tree-covered Bloomington Rail Trail and keep Z2 rides early. Clear Creek, Limestone Greenway, and Karst Farm Greenway stay useful when the sun gets high. Winter is not exactly the most forgiving at times. Runners manage dress and keep workouts simple. Cyclists bring the bike that can get gunked up with snow melt and sand, and studded tires can make commuting and steady miles feel doable.

Upcoming

Coming soon in Bloomington

All races within 80 km, sorted by date. Click any event for the route, registration link, and past results.
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What runners & riders are signing up for

If you're traveling — or just curious — here's where the action is across two of the most active markets on TrainerDay.