Racing for Good: 2026 Calendar for Fun Runs that Give Back

More than 50 charity races, fun runs, and fundraising events are scheduled across the greater Milwaukee area in 2026, supporting causes from heart disease research and childhood cancer to organ donation awareness and disability services.

The calendar spans every month of the year, with events on road, trail, and rail trail courses throughout Milwaukee, Wauwatosa, Shorewood, Whitefish Bay, Elm Grove, Brookfield, West Allis, and surrounding communities. Collectively, these races have raised millions for local and national nonprofits — and most welcome walkers, families, and first-time participants alongside competitive runners.

Winter races

The racing season begins in January with the Samson Stomp & Romp at the Milwaukee County Zoo (January 18), now in its 45th year. The 5K competitive run (capped at 1,500), 2-mile fun run/walk, and 1-mile kids romp benefit the Zoological Society of Milwaukee. Registration is $35 pre-race and includes zoo admission, parking, a long-sleeve shirt, and post-race snacks.

Valentine's Day brings one of Milwaukee's most beloved charity races: the Steve Cullen Healthy Heart Club Run (February 14) in Wauwatosa's Hoyt Park area. Celebrating its 30th anniversary, this 8K timed run and 2-mile fun run/walk honors Milwaukee Alderman Steve Cullen, who died of a heart attack at age 40. The event has raised over $650,000 for heart research at the Medical College of Wisconsin's Cardiovascular Research Center. Registration runs $30–35 individually or $100–125 for a family of four, and the famous post-race Cullen Family Chili is a tradition. Register by January 31 for a guaranteed dry-fit shirt.

The Fight for Air Climb (March 21) at 411 East Wisconsin Center challenges participants to climb 30 floors to benefit the American Lung Association. Each climber must raise a $100 fundraising minimum, with additional incentives at the $175 level. Wave times begin at 8:30 AM, and the average climb takes about 11.5 minutes. This is a unique stair-climb format rather than a traditional road race.

Spring races

April is packed with fundraising events. The Journal Sentinel Milwaukee Marathon Weekend (April 11–12) is the city's marquee running event, featuring a USATF-certified, Boston-qualifying marathon and half marathon on Saturday and a 5K on Sunday. The race partners with charities including the MACC Fund and sells out annually. The expo takes place April 10 at the Baird Center.

The Brew City Marathon, Half, 10K & 5K (April 18) runs flat, fast USATF-certified courses along the Oak Leaf Trail from Veterans Park. It partners with Hunger Task Force, Milwaukee's free and local food bank. Post-race festivities include bratwurst and Broken Bat Brewery beer. Registration ranges from $39.99 (5K) to $99.99 (marathon).

Three charity races land on April 25:

• Cream City 5K & Kellan's Kids Run at Greenfield Park in West Allis raises awareness for organ, tissue, and eye donation. Founded by double lung transplant recipient Jesse Pagels, this 501(c)(3) has donated over $150,000 to Versiti Organ and Tissue and other organizations since 2016. The 5K is $35; Kellan's Fun Run for kids 10 and under is $15.

• Bosom Buddy 5K in Cedarburg supports breast cancer awareness with a 5K and 1-mile option through the historic downtown.

• Moonlight Meltdown 5K & Sunset Safari 10K in Belgium (Ozaukee County) benefits Belgium Fire and Rescue, Rocket Academy, and Snow Runners Ltd. The 10K includes a 1.2-mile trail section through Harrington Beach State Park.

The Run 4 Water MKE 5K (April 18–26) on Milwaukee's lakefront directs all proceeds to Engineers Without Borders at UW-Milwaukee for water distribution projects in rural Guatemala.

In May, the Cedarburg Half Marathon & 5K (May 23) benefits Camp Odayin at Camp Lutherdale, which serves children with heart disease. The flat, certified bike-path course now includes a new RUCK Half Marathon option. Post-race flapjack breakfast included.

The Strain for the Brain 5K (May 30) at Veterans Park funds brain tumor research at Froedtert & the Medical College of Wisconsin, with a 2026 fundraising goal of $200,000. The event has donated over $600,000 since 2010. Brain tumor survivors participate free, and fee waivers are available for anyone who requests them. Registration starts at $30.

The Ray of Hope Run (May 30–31) at Hoyt Park in Wauwatosa raises money for ovarian cancer research at the Medical College of Wisconsin's Women's Health Research Program, having donated $17,000 in 2023 alone. Distances include a chip-timed 5K, 2K/3K walk, and kid run.

Summer races

The Brewers Community Foundation 5K/10K Famous Racing Sausages Run/Walk (July 15) at American Family Field lets participants run alongside the iconic Racing Sausages and finish on the stadium's warning track. Proceeds benefit the Brewers Community Foundation, Fisher House Wisconsin, and the Clement J. Zablocki VA Medical Center. Registration includes a commemorative t-shirt and Brewers game ticket voucher.

The Race to Cure Sarcoma (July 11) in Franklin supports the Sarcoma Foundation of America, which has raised $8.5 million through 130+ events nationwide. The Portal Fish Day Run/Walk/Roll (July 18) in Port Washington, now in its 41st year, uses the Ozaukee County Interurban Trail (a rail trail) and benefits Portal, Inc., which serves adults with intellectual and developmental disabilities. Registration is $35 early, $40 race day (cashless only).

The Storm the Bastille 5K runs through illuminated downtown Milwaukee on a Friday evening during the Bastille Days Festival (July 9–12), starting around 9 PM from Cathedral Square Park. The Color Run Milwaukee (July 11) offers a 3–5K untimed experience with color stations and a mini music festival; its "Paw Admission" virtual option sends 100% of proceeds to pet welfare organizations.

The Walk for Wishes (August 29) at Milwaukee County Zoo supports Make-A-Wish Wisconsin, which currently has 330+ wishes in progress. Registration is free with fundraising encouraged. The Tunnel to Towers 5K (expected summer 2026) in New Berlin benefits the Tunnel to Towers Foundation for fallen first responders and military heroes — 93% of all funds go directly to programs.

Trail races and rail trail courses

Several events use the area's excellent trail network. The Trailbreaker Marathon & Half (March 29) in Waukesha is a USATF-certified Boston Qualifier running approximately 6 miles of city streets, 15 miles of the Fox River Trail and Glacial Drumlin Trail (rail trails), and 5 miles of the Ice Age Trail. It benefits the Park Foundation of Waukesha, with the Kids 1K donating 100% of its $5 fee.

The Wisconsin Trail Assail Series offers seven trail races from April through October across Waukesha County parks including Lapham Peak, Nashotah Park, Menomonee Park, Fox River Park, Pike Lake, and Minooka Park. Each event offers 5K, 10K, and half marathon distances with a free Kids 1K.

The Golden Kettle Trail Series runs seven events from April through October across Kettle Moraine locations with short (~3 mi), mid (~5 mi), and long (~12 mi) distances, featuring flexible start windows, free craft beer, and wooden finisher medals.

The Adrenaline Races (mid-July) on the Eisenbahn Trail in West Bend offer a USATF-certified Boston Qualifier on a scenic rail trail with distances from 5K to marathon. The Badgerland Striders Half Marathon (late August) runs along the Oak Leaf Trail through Estabrook Park in Shorewood/Milwaukee.

The Little Warrior Foundation 50K & 5K (mid-November) at Lapham Peak in Delafield is a demanding trail ultra with 3,610 feet of elevation gain across five woodland loops, raising funds for childhood cancer through the Little Warrior Foundation.

Suburban communities

Wauwatosa is a hub for charity races beyond the Cullen Run. The Run Tosa Run 5K (mid-May) starts at 69th and North Avenue in East Tosa, with net proceeds benefiting Ronald McDonald House Charities Eastern Wisconsin. Registration starts at $25 for the 5K and $12 for the kids' half-mile run. Joe's Run, Walk & Roll (September 12) at Hoyt Park benefits Broadscope Disability Services with a fully accessible route, 5K run, 3K fun walk/roll, and free kids' fun run with parent registration. The HartFest 5K during the annual HartFest festival uses paved bike paths and gravel trails through Hart Park.

Whitefish Bay hosts the Dominican KnightRun 5K (September, typically the third Saturday) at Dominican High School on Silver Spring Drive, with proceeds directly benefiting the school. Registration includes a t-shirt and swag bag.

Elm Grove hosts the Kelly Johnson Foundation Labor Day 5K (September 5) at Elm Grove Village Park, a chip-timed race limited to 250 participants benefiting the Kelly Johnson Foundation. Online registration closes at noon the Wednesday before, with race-day registration available from 8–8:45 AM.

Brookfield features the St. John Vianney Hog Jog (June 6), a 5K fun run and 2-mile fitness walk at 1755 North Calhoun Road benefiting the parish. Professional chip timing, age-group medals, and prizes from Performance Running Outfitters await. Register by May 23 for a guaranteed dry-wick shirt.

Shorewood hosts the Hot Cider Hustle Half Marathon & 5K (October 24), with a USATF-certified course along the Oak Leaf Trail that benefits the Wisconsin Ovarian Cancer Alliance. Every finisher receives a mug of hot apple cider and caramel apples.

West Allis/Greenfield sees Nancy's Run, Rock & Stroll (September 12) at Greenfield Park's Cool Waters Pavilion, benefiting the Wisconsin Ovarian Cancer Alliance (WOCA). Ovarian cancer survivors register free, and teams of 10+ get a $5 discount.

Fox Point celebrates its centennial with the Fox Point Centennial 10K/5K (June 13).

Fall races

The Milwaukee Lakefront Marathon, Half Marathon & 5K (October 3–4) is Wisconsin's oldest and largest marathon, crossing the iconic Hoan Bridge with 40%+ of the course along Lake Michigan. The This Time Tomorrow Foundation charity team allows runners who raise $100+ for a cancer patient to receive a custom jersey. Limited to 2,500 marathon and 3,500 half marathon runners; produced by Badgerland Striders.

Major health walks cluster in the fall. The Walk to End Alzheimer's — Milwaukee County (October 3) at Henry Maier Festival Park (Summerfest Grounds) is the world's largest event to fight Alzheimer's, held in 600+ communities. Registration is free with fundraising encouraged. NAMIWalks Wisconsin (typically early October) at the Milwaukee County Zoo supports NAMI Southeast Wisconsin's mental health programs that impacted 21,000 people in 2024 — registration, zoo admission, and parking are all complimentary. Making Strides Against Breast Cancer — Milwaukee (typically early October) is the American Cancer Society's annual lakefront walk, now in its 30th year. The SE Wisconsin Heart & Stroke Walk/5K Run has a $685,000 fundraising goal for 2026, with the walk free to register and the 5K at $45.

The Lakefront Discovery Run (October 31, Halloween) at Veterans Park offers a costumed 15K and 5K with candy-laden aid stations, a "Monster Mile," and free beer for all participants. The free Kids Costume Race starts at 8:45 AM.

Thanksgiving Day (November 26) presents two major options. The Festival Foods Turkey Trot at American Family Field offers a 2-mile walk, 5-mile timed run, and 2-mile Dog Jog benefiting Boys & Girls Clubs and YMCAs — the event has donated over $4.8 million across 17 years. The Milwaukee Turkey Trot on Lincoln Memorial Drive along the lakeshore supports Hunger Task Force with a 5K, 8K, and kids' dash, finishing with Cranky Al's donuts.

The Wisconsin Brewery Running Series runs monthly events from April through November at Milwaukee-area breweries including Lakefront Brewery, Broken Bat Brewing, MobCraft, and Westallion Brewing. Each casual, untimed ~5K includes craft beer and a collector's pint glass, with 10% of proceeds going to local nonprofits.

More options

Many races that aren't explicitly branded as "charity events" still offer charity bib or fundraising partnership options — the Milwaukee Marathon's MACC Fund partnership and the Lakefront Marathon's This Time Tomorrow Foundation team are prime examples. For health-focused walks, the Alzheimer's Association, American Heart Association, American Cancer Society, and NAMI all offer free registration with encouraged fundraising, making them accessible entry points for anyone wanting to support a cause without a race entry fee. Most road race registrations range from $25–50 for a 5K and $80–150 for a half or full marathon, with early-bird discounts typically saving $5–15.