5K races near Oconomowoc

The 44th Milwaukee Lakefront Marathon, Wisconsin's largest and oldest marathon, is set against the backdrop of Milwaukee, offering scenic views of the city's skyline. This established event provides a significant challenge within the local running scene, rooted in a rich history along the Lakefront. The course travels along the Lake, presenting views throughout the race. Runners will experience the iconic Hoan Bridge as a key feature, making for a journey through Milwaukee on a route celebrated for its distinctive path.

The Wisconsin Cheese Run is a running event in Muskego Park, with options around 1 km, 3.2 km, and 5 km. It is designed for runners, walkers, and kids, making the field broader than a standard road race lineup. A ruck option offers a strength-focused alternative to the regular run or walk. The event begins at Muskego Park. Every finisher receives a free stick of cheese, and children get an additional cheesy finisher surprise. Wisconsin also has a related cheese-branded race history in Hilbert, where the Cheesehead Run used certified 5K and half marathon courses from Main Street through Calumet County countryside toward Forest Junction, with the half marathon returning on the Fox River Trail.

The Milwaukee Beer Run 5k & .05k begins and ends at The Bavarian Bierhaus in Glendale, north of Milwaukee. This October running event connects to Milwaukee's Original Oktoberfest. It offers a chip-timed 5K for runners and walkers, plus a very short .05K option covering only 54 yards. The 5K follows the Oak Leaf Trail out and back, leading finishers directly into the Oktoberfest festivities at Old Heidelberg Park. Registration provides all-day festival access, a Beer Run sweatshirt, a collector's cup, and a post-race craft beer or root beer from The Bavarian Bierhaus. The event benefits Hunger Task Force via a donation and food drive. Its setup accommodates all ages, including club runners, casual joggers, walkers, families, and those primarily interested in the short dash and the subsequent party.

Race for Open Space on Nantucket offers 5K, 10K, and 2-mile distances, allowing runners, walkers, and joggers to select a distance suitable for their day. The course follows a rolling route through the Middle Moors, an island landscape the event helps protect. The race directly supports the Nantucket Conservation Foundation, with proceeds funding its science, restoration, and stewardship of open spaces on the island. With over two dozen events held, it functions as a local tradition centered on crossing the land it benefits.

The Spooky Sprint - Milwaukee is a Halloween-themed race morning at Estabrook Park in Shorewood, offering 5K, 10K, half marathon, 1-mile, and Kid's Dash options. Bodies Race Company organizes the event as part of its local race series, catering to runners seeking chip-timed results and families looking for a low-pressure seasonal run. The courses feature flat, paved loop or out-and-back routes within the park. The 1-mile and Kid's Dash remain untimed. Children 10 and under may enter the dash for free if they forgo the shirt and medal package. Costumes are encouraged, with trick-or-treat aid stations enhancing the Halloween theme. The finish area provides treats, complimentary photos, a DJ, and a costume contest. The 5K, 10K, and half marathon participants receive custom bibs, designer shirts, finisher medals, live results, and age-group awards. Youth pricing is available for the 5K and 10K.

National Sweetest Day marks the conclusion of the Wisconsin Trail Assail Series in Nashotah, Wisconsin, coinciding with the National Sweetest Day holiday. This event offers trail running and walking options: 5K, 10K, and half marathon distances, along with a 1K for children under 10. The event typically hosts 100 to 500 participants, taking place within Nashotah Park. The course features wide, maintained trails covered in wood chips. Over 90% of the race unfolds within the park's wooded areas, passing Forest Lake and Grass Lake. The terrain is characterized as fast and flat, suitable for trail runners seeking less technical challenges on longer distances. Families are included, with children in the 1K receiving their own bibs, and this kids' race is complimentary for registered parents.

The Tombstone Trot guides runners and walkers through Prairie Home Cemetery, featuring a 5K run, a 2-mile walk, a Kiddos Run, and a 5K ruck. This October community race is organized by Prairie Home Cemetery and Silver Circle Sports Events, centered on the cemetery’s anniversary and its extensive local history. The route remains within the cemetery grounds, making the setting integral to the event. Participants pass a historic Waukesha landmark instead of a typical road course. A portion of the entry fees benefits Friends of Prairie Home Cemetery, a 501(c)(3) nonprofit, with funds designated for a monument and flagpole in the newer Veterans section. The event also offers a 50/50 raffle and sells Prairie Home Cemetery history books, contributing to a preservation fundraiser atmosphere rather than a standard 5K.

The Dia de los Muertos Run/Walk is a 5K run-walk-roll starting at 9 a.m. at Gill Memorial Park in Milpitas, followed by a wellness fair from 10 a.m. to noon. Registration is available for adults and youth, with options including a medal, shirt, and race swag bag, catering to runners, walkers, wheelchair users, families, and kids. The route begins and ends at the park, incorporating the Hetch Hetchy Trail, and can also be navigated on city sidewalks or streets, ensuring accessibility. Following the 5K, the event incorporates Dia de Muertos traditions and community health activities, featuring Mariachi music, Bay Area Aztec dance performances, sugar skull face painting, children's crafts, and wellness resources.

The Hot Cider Hustle in Shorewood, Wisconsin, offers a half marathon and several 5K race options. Participants can select a timed 5K, an untimed 5K, a kids’ 5K for those 12 and under, or virtual options for the 5K and half marathon. The signature finish-line offerings include hot cider, a caramel apple, and a finisher’s mug for all participants. The kids’ race is untimed, providing the same cider, caramel apple, and mug. The #HotCiderHustle tag serves as a straightforward method for sharing race photos.