Races Near Me: Upcoming Running Races

Race #1: Winter Run Series Join us for the 22nd annual Winter Run Series—Wisconsin’s largest running series! This exciting event takes you through the heart of Milwaukee and its scenic suburbs, showcasing the city’s charm and beauty. Spanning six events throughout the winter season, the series is the perfect way to stay active and embrace the winter months, all while celebrating your favorite holidays. Bring the whole family and choose between the 5K or 10K distances. Let’s conquer the cold together!

The 22nd running of Wisconsin’s largest running series is set to explore the inner workings of Milwaukee and its beautiful suburbs. This series plays host to six events throughout the winter season, surrounding your favorite holidays. Bring the family to participate in the 5K or 10K. Let's Conquer the Cold! The Pumpkin Run | Sunday, October 25 | Oconomowoc, WI The Elf Run | Sunday, November 22| Hales Corners, WI Run Into The New Year | Wednesday, December 31 | Wauwatosa, WI The Big Chill | Sunday, January 17 | South Milwaukee, WI Cupid Shuffle | Sunday, February 14 | Shorewood, WI Luck of the Irish | Sunday, March 14 | West Allis, WI 6 EVENT SERIES REGISTRATION BUNDLE Join us for the 2026-2027 Winter Run Series! Start the series off with the Pumpkin Run and finish with the Luck of the Irish while completing The Elf Run, Run Into The New Year, The Big Chill, and The Cupid Shuffle in between! **Must sign up for the 6 Event Series to earn the series medallion!

Join the Oconomowoc Public Education Foundation (OPEF) for a 1-mile or 2-mile run to support our schools!  This fall, OPEF is striving to raise at least $25,000 to fund new gymnastics equipment for the elementary schools, sound system improvements at the middle school, and more! OPEF is a collaborative partner of the Oconomowoc Area School District (OASD).  OPEF raises and   provides funds for innovative educational opportunities and experiences not funded in the core school district budget – including classroom grants, facilities improvements, and innovative curriculum.  OPEF has given more than $500,000 to the OASD in the past 18 years.  Help OPEF continue the legacy of gifts from the community…to the schools…for our future! Wear your OPEF Trick or Trot shirt, your school swag, or your Halloween costume for this fun after-school event that will have music, costumes, candy, and prizes!

Welcome to the only race on Earth where you don’t just cross the finish line—you strut, flap, and cluck your way there! 🏃‍♂️💨 Forget boring medals and generic t-shirts. At Run Like a Rubber Clucker, you’ll earn bragging rights, rubber chickens 🐓, and the eternal glory of being a certified “Rubber Clucker.” Whether you’re a speed demon chasing a PR ⏱️, a casual jogger looking for some laughs 😂, or just here for the rubber poultry, this race is built for you. What to expect: Feather-flapping fun from start to finish 🎉Swag that will have your neighbors asking, “Wait… did you really get a rubber chicken for running?” 🤔A course full of runners who don’t take themselves too seriously (but still run like the wind) 🌬️ So lace up, loosen up, and let your inner chicken out. Because at this race, everyone’s a clucker. 🐔👏

The All Access Pass is your ticket to unlimited running fun! 🏃‍♂️🏃‍♀️ One low price gives you entry into all Silver Circle Sports Events–owned races from November 1, 2025 through October 31, 2026—that’s 30+ races and over $1,000 in value. No lines, no hassle… just show up and run. 🎉 All SCSE-owned events are included, plus all brand-new 2026 events*! That’s more than 100 races on your calendar. *Note: The Lake Country Triathlon isn’t included, but you’ll get a special discounted registration option. Client/third-party events aren’t included, but if there’s space, you may be able to jump in—just ask!

Introducing OconoWattaWoc, a brand-new 5K, & 10K run/walk/ruck on the Interurban Recreation Trail connecting Oconomowoc and Watertown. Yes, we made up the name. No, we are not apologizing. The 5K, & 10K are perfect for runners, walkers, ruckers, families, first-timers, seasoned racers, and anyone who enjoys fresh pavement, questionable event names, and the phrase “old trolley line” more than they probably should. Come run the trail. Walk the trail. Ruck the trail. Pronounce the name however you want. OconoWattaWoc: Two towns. One trail. Too many syllables.

11/9/20025 - Registration Update Registration has closed for the series. If you would like to attend the series, please contact us and we will open it for you.   🗓️ 10/29/2025 – T-Shirt Deadline Update The t-shirt deadline has now passed. Series runners will be contacted after Veterans Day to confirm their shirt size. Shirts will be handed out at future events in the series. If you’d still like to register for the All Access Pass, select “Registered After T-Shirt Deadline” during signup, then email us to let us know you’d like to upgrade. We’ll take care of the rest and move you into the pass. Thanks for keeping those miles (and emails) coming! — Sean K. OsborneChief T-Shirt Sorter 👕   2025–26 Wisconsin Chilly Willy Winter Run Series❄️🏃‍♂️🏃‍♀️ Presented by Silver Circle Sports Events, LLC Bundle up and lace up—Old Man Winter is ready to race! ❄️ Join us for the 2025–26 Wisconsin Chilly Willy Winter Run Series, where chilly temps meet hot competition acr

Thanksgiving morning is better when you start it together. Thanksgiving morning at Oconomowoc High School — start a new family tradition before the turkey takes over.Warm indoor space and restrooms — because November in Wisconsin likes to keep things interesting.Something for everyone — choose the 5K, 10K, 5K Walk, 5K Ruck, or the Kiddo’s 1K.Free hot chocolate bar — earn it first, then build the perfect cup.Flat, family-friendly course — great for runners, walkers, first-timers, and competitive relatives.Locally owned and produced by Silver Circle Sports Events, LLC — a hometown event built by people who live and work here.Custom awards by Oconomowoc-based Ridgeway Woodworks, LLC — something far better than a plastic participation trophy collecting dust next to the treadmill. Come run, walk, ruck, cheer, sip hot chocolate, and make Thanksgiving morning a little more memorable. The Oconomowoc Great Gobble Wobble is proud to be part of the Wisconsin Chilly Willy Run Series. NEW for 2026 - 1K Kiddo's Gobble Bundle! Bring Your Flock. Get Rewarded. Thanksgiving morning is better with friends, family, coworkers, neighbors, and that one cousin who says they “do not run” but somehow wins the family 5K. When you register for the Great Gobble Wobble, you will receive a personal referral link in your confirmation email. Share it with your crew by text, email, or social media. For every five friends who register using your link, you’ll earn $25 back on your registration. Have a crew of four or more? Create or join a team, and we will preassemble your team’s race packets—shirts, bibs, and race information—in one convenient bundle for easy pickup. Bring the runners. Bring the walkers. Bring the people who are mainly here for hot chocolate and pie-earned bragging rights. The more people you bring, the more fun Thanksgiving morning becomes—and the more you can earn back. 🦃🏃‍♀️🏃‍♂️

Get ready to lace up your running shoes and embrace the holiday spirit at the Naughty or Nice List Run in Oconomowoc, Wisconsin, on Saturday, December 5, 2026! This festive event welcomes participants of all ages and fitness levels to choose their side—Naughty or Nice—and enjoy a fun morning of running, walking, rucking, and holiday cheer. When registering, decide whether you're feeling Naughty or Nice by selecting the corresponding event. Don’t worry—it’s the same race, at the same time, on the same planet. The two options simply divide everyone into teams and add a little friendly competition to race day. Team Naughty and Team Nice will each have their own distinct shirt color, so you can proudly show off your holiday spirit and team allegiance. Want to run with friends? Create a sub-team and bring your whole Naughty or Nice crew along. Whether you're racing for bragging rights, holiday fun, or just trying to convince Santa you've turned things around, this is a great way to celebrate the season together.

Bring the family (and the fun) to our Noon Year’s Event Run 🎉, now at the new location: Meadow View Elementary School 🏫 in Oconomowoc! We’ve expanded this daytime New Year’s Eve celebration to include a 5K 🏃‍♂️, 1.5 mile walk, alongside the beloved free kids’ run 👧👦. Whether you're racing or walking, enjoy all the excitement in the comfort of a large, heated building ❄️🔥—perfect for staying warm before and after the event. It’s the perfect way to ring in the noon year with community, laughter, and a cozy place to celebrate! This event is brought to you through a partnership with the City of Oconomowoc Parks and Recreation Department, Silver Circle Sports Events, LLC, and the Silver Circle Foundation, 501(c)(3). Activities Include 🎉 🎲 Play games and win make-and-take kits—get crafty at home later! 🏃‍♂️ Races for ages 1 and up! Shuffle through the snow, snag a finisher woodle, and smile for finish photos (posted after the event). The Kiddos 1K event & activities are free, but registration is required. 🎶 Tunes to rock out to while you enjoy the festivities. 📸 Selfie station with fun props—smile and capture the memory! 🎊 Be ready at noon for the official ball drop, confetti cannons, noisemakers, and a whole lot of fun. At 12 p.m. sharp, join the countdown as the Noon-Year’s Ball drops from the Western Lakes Fire Department’s ladder truck—a celebration like no other! 🚒✨

☘️ Shake Your Shamrocks 5K, 10K & 2-Mile Walk ☘️ We're back at Lucky Chucky's... and the luck of the Irish is calling! Everyone's a little Irish on St. Patrick's Day. Some celebrate with green beer. Others celebrate with corned beef and cabbage. We prefer to celebrate by lacing up our running shoes and chasing finish lines. Whether you're racing the 5K, taking on the 10K, or enjoying the family-friendly 2-Mile Walk, Shake Your Shamrocks is your chance to shake off winter and welcome spring one stride at a time. The fun begins and ends at Lucky Chucky's, where festive vibes, great company, and a well-earned post-race celebration await. Throw on your favorite green, sport your lucky socks, wear that shamrock hat you've been saving all year, or show up dressed like the leprechaun you were clearly destined to be. Around here, the more Irish spirit, the better! As one of the final races in the Wisconsin Chilly Willy Winter Run Series, Shake Your Shamrocks is your chance to celebrate everything you've accomplished through another Wisconsin winter. The snow is melting, spring is on the horizon, and you've earned the right to cross one more finish line before the seasons change. So gather your lucky charms, round up your family and friends, and come shake your shamrocks with us! No luck required... just a little determination, a splash of green, and a willingness to have a shamrockin' good time! ☘️🏃🍀

Welcome to the Wisconsin Trail Assail Series! 🌲🏃‍♂️🏃‍♀️ Experience seven races over seven months—building to an epic series finale. The Wisconsin Trail Assail tours some of the most scenic routes in Waukesha County and Wisconsin State Parks, with courses for every level. Pick your challenge each month: 5K, 10K, or Half Marathon. Run it, walk it, chase a PR, or just collect trail miles with friends—the series is proudly walker-friendly. Why you’ll love it: Varied terrain and views all season longConsistent, well-marked courses and friendly vibesA series-ending championship to cap your journey Ready to hit the dirt? Join the Wisconsin Trail Assail and stack finish lines all season. WTA All Access Pass & Rucking!   🚀 Skip the Lines With The WTA All Access Pass! 🏃‍♂️ WTA All Access Pass? Your ticket to skipping the packet pickup line and heading straight to the start line!  How It Works:✔ Register for the series in any distance 🏅✔ Opt ou

🏃‍♂️ The Non-Cancelled Marathon: A Race Built to Last! 🏅 The Non-Cancelled Marathon: Fast by Design. Legendary by Nature. Born in 2020 as a bold answer to race-day uncertainty, the Non-Cancelled Marathon has grown into a go-to event for runners hungry for PRs and Boston qualifiers. This is not just flat. It is laser-flat, lightning-fast, and fully certified, a course built to reward strong legs and smart pacing. Even better, it is a dream for spectators. Your fans and crew can cheer you on up to eight times without budging, then roll straight into the start and finish to witness the moment you make it official. If you are ready for a high-energy, runner-first marathon that delivers speed, support, and unforgettable vibes, lace up and join us. This is the race that shows up. Course certification number WI21003DM.

Make sure you follow us on Facebook for the latest updates. I TRI, THEREFORE I AM! ELEVEN YEAR ANNIVERSARY! Join us on Saturday, July 25, 2026 for the Lake Country Triathlon, one of the Midwest premiere endurance challenges. Located in the heart of beautiful Lake Country, Wisconsin. The Lake Country Triathlon offers an amazing race experience that begins with a swim in the clear waters of Lac La Belle, an incredible scenic ride through the rural glacial landscape of SE Wisconsin, and a run through the charming community of Oconomowoc.  This year is our 11th year since re-establishing the triathlon in 2015. Over the past 11 years, we've seen athletes from nearly every state, Canada, and even Europe. We are the perfect setting for the first time triathlete and provide challenging competition for the world's best elite triathletes. We're hoping this year will be our largest and best Lake Country Tri yet and we hope you'll join us in July! Alan Halfen Race Director

The ONLY race around Lac La Belle! 8 Mile & Half Marathon Run 🏃‍♀️🏃‍♂️ Discover the beauty of Lac La Belle 🌊 on this unforgettable 8-Mile and Half Marathon course. Starting at the Village Green in downtown Oconomowoc 🏞, runners head north along the picturesque isthmus between Fowler Lake and Lac La Belle. The course then winds west through the charming Village of Lac La Belle 🏡, tracing the shoreline before opening into peaceful countryside roads 🌳. On the return, the route hugs the lake’s western edge, offering sweeping water views 🌅 all the way back to Wisconsin Avenue. The final stretch is a flat, fast push to the finish at City Beach 🏖—right on the shores of Lac La Belle.