Guide to 2026 Fun Runs and Races in Greater Milwaukee

Whether you're chasing a Boston qualifier, introducing your kids to racing, or just looking for a fun Saturday morning adventure, Milwaukee's running scene delivers year-round. From the iconic Hoan Bridge crossing at the Lakefront Marathon to quirky brewery runs and challenging ultras through Kettle Moraine's glacial terrain, this comprehensive guide covers every race worth knowing about in southeastern Wisconsin. Tim's insider tips will help you pick the perfect events and show up prepared.

Winter races: January through March

Samson Stomp & Romp (Milwaukee County Zoo)

Date: Sunday, January 18, 2026
Location: Milwaukee County Zoo, 10001 W. Bluemound Road
Distances: 5K competitive run (9:30 AM), 2-mile fun run/walk (10:15 AM), 1-mile kids romp (10:45 AM)

This 45th annual event transforms a winter zoo visit into a running adventure. The 5K is capped at 1,500 runners, so register early. Registration includes zoo admission for the entire day—a $15 value—plus parking, a long-sleeve shirt, and post-race snacks. Age group winners receive adorable gorilla trophies.

Insider tip: No strollers allowed on course for safety reasons. The 1-mile kids romp is perfect for children who want their own race experience.

Registration: $35 pre-registration ($40 race day)
Website: milwaukeezoo.org/visit/upcoming-events/samson-stomp

Frosty 5K

Date: Saturday, January 24, 2026
Location: Waukesha
Distances: 5K, Kids Run

A family-friendly winter 5K that embraces the cold. Includes a dedicated kids run for the younger members of your family.

John Dick Memorial 50K

Date: Saturday, February 7, 2026
Location: Southern Kettle Moraine State Forest (D.J. Mackie Group picnic area)
Distance: 50K trail

Badgerland Striders' annual ultra honoring long-time club member John Dick. Expect temperatures between 26-41°F and possibly snowy, icy trails. This race builds character—and a great story to tell at the finish.

Best for: Ultra runners seeking early-season challenge

Steve Cullen Healthy Heart Club Run

Date: Saturday, February 14, 2026 (Valentine's Day) — 30th Anniversary!
Location: Wil-O-Way Recreation Center, Wauwatosa (Hoyt Park area)
Distances: 8K timed run, 2-mile untimed fun run/walk, virtual option

This beloved Valentine's Day tradition honors Milwaukee Alderman Steve Cullen, who died of a heart attack at age 40. The race has raised over $600,000 for heart research at the Medical College of Wisconsin. Register by January 31 for a guaranteed long-sleeve dry-fit shirt.

Post-race: The famous Cullen Family & Friends Chili—arguably worth the price of admission alone.

Registration: ~$30-35 individual, ~$100-125 family of four
Website: cullenrun.com

Flannel 5K/10K

Date: Saturday, February 14, 2026
Location: Menomonee Falls
Distances: 5K, 10K, Kids Run

Valentine's Day meets flannel—because Wisconsin. A fun themed winter event with a kids run option.

Arktos Winter Ultra

Date: February 28 – March 1, 2026
Location: Southern Kettle Moraine State Forest
Distances: 6-hour, 12-hour, 20-hour (solo or relay teams up to 4)

Named after the Greek word for "bear," this timed ultra challenges you to complete as many trail loops as possible. Limited to 160 runners and sells out early. Perfect for first-time ultra runners who want a supported, low-key introduction to long-distance trail running.

Registration: ~$70-90 depending on distance
Website: goldenkettletrailseries.com/arktos

Lucky Leprechaun 7K

Date: Saturday, March 7, 2026
Location: Leff's Lucky Town, Milwaukee
Distance: 7K run/walk

St. Patrick's Day festivities come early with this festive 7K featuring two free Miller Lites (or soft drinks), a blingy bottle opener medal, costume contest, live music, and fire pits with marshmallow roasting. The $49.99 registration increases after March 5.

Website: luckyleprechaunrun.com

Pettit Indoor Marathon & Relay

Date: March 7-8, 2026
Location: Pettit National Ice Center, Milwaukee
Distances: Half Marathon, Marathon Relay

Run around an Olympic speed skating track—indoors. This unique event eliminates weather concerns entirely while offering a Boston-qualifying option in a temperature-controlled environment.

Grafton Lucky 5K

Date: Saturday, March 14, 2026
Location: Grafton
Distance: 5K

St. Patrick's Day themed community run in Ozaukee County.

First Call 5K, 10K & Half Marathon

Date: Sunday, March 22, 2026
Location: Waukesha
Distances: 5K, 10K, Half Marathon (trail)

Fast trail course marking the beginning of trail racing season in Waukesha County.

Trailbreaker Marathon & Half

Date: Sunday, March 29, 2026
Location: Schuetze Recreation Center, Waukesha
Distances: Marathon, Half Marathon, 10K, 5K, Walk, Kids 1K, Ruck options

This USATF-certified Boston Qualifier covers approximately 6 miles of city streets/sidewalks plus 20 miles of paved Fox River Trail and Glacial Drumlin Trail. Marathon runners tackle 5 miles of Ice Age Trail to Lapham Peak, where you'll ring the bell at the observation tower at the halfway point. Super-flat and good for PRs.

Best for: Boston qualifiers, trail running beginners (shorter distances)
Website: runsignup.com/Race/Info/WI/Waukesha/Trailbreaker

Spring races: April through May

Time to Paddy 5K/10K and Lucky 13.1

Date: March 21, 2026
Location: Milwaukee
Distances: 5K, 10K, Half Marathon, 1 Mile, Kids Run

St. Patrick's Day themed event with multiple distance options for the whole family.

DoNot Stop Half Marathon & 5K/10K

Date: Saturday, April 4, 2026
Location: Milwaukee
Distances: 5K, 10K, Half Marathon, Kids Dash, 1 Mile

The name tells you everything: FREE donuts at the finish line. Youth pricing (12 and under) is just $17, making this an affordable family option. The Kids Dash gives young runners their own race experience.

Website: runsignup.com/Race/WI/Milwaukee/DonotStopWestAllis

Milwaukee Marathon Weekend

Date: Saturday-Sunday, April 11-12, 2026
Location: Start: Downtown Milwaukee (N. Jackson St); Finish: Humboldt Park
Distances: Marathon & Half (Saturday 7:00 AM), 5K (Sunday), "4RUN4 Challenge" (marathon or half + 5K)

The spring counterpart to the Lakefront Marathon, this event sells out every year. The USATF-certified course is a legitimate Boston Qualifier, weaving through vibrant Milwaukee neighborhoods with lakeside views. The post-race Brewfest-style party at Humboldt Park features local breweries including Supermoon Beer, Torzala Brewing, New Barons, and Vennture Brew Co.

Expo: Friday, April 10, 12:00-6:00 PM at Baird Center (400 W. Wisconsin Ave)
Website: milwaukeemarathon.com

NK50K (Northern Kettle 50K)

Date: Saturday, April 11, 2026
Location: Greenbush, Northern Kettle Moraine
Distances: 50K, 25K (point-to-point)

A challenging point-to-point ultra from Ridge Road Trailhead to Greenbush Group Camp. The course reaches the highest point in Northern Kettle Moraine State Forest, with rolling ski tracks and rocky Ice Age Trail sections. Bus transportation provided from finish to start at 6:00 AM.

Registration: $24.60
Website: ultrasignup.com/register.aspx?did=126079

Wisconsin Trail Assail Series Begins

Date: April 11, 2026 (first race: "Run from the Taxman")
Location: Lapham Peak State Park
Distances: 5K, 10K, Half Marathon

This seven-race trail series runs April through October across Waukesha County parks and Wisconsin State Parks. The April kickoff at Lapham Peak coincides with tax deadline—hence the name. Free Kids 1K with parent registration. Walker-friendly and cupless (bring your own cup).

Full 2026 Series Schedule:

• April 11: Run from the Taxman (Lapham Peak)

• May 10: Mother's Day Run (Nashotah Park)

• June 14: Father's Day Run (Menomonee Park)

• June 27: Independence Day Run (Fox River Park)

• August 1: National Watermelon Day Run (Pike Lake State Park)

• September 19: Procrastination Day Run (Minooka Park)

• October 17: National Sweetest Day Run (Nashotah Park)

Website: runsignup.com/Race/WI/Oconomowoc/WisconsinTrailSeries

Brew City Marathon, Half, 10K & 5K

Brew City Marathon, Half, 10K & 5K

Date: Saturday, April 18, 2026
Location: Veterans Park, 1750 N. Lincoln Memorial Drive
Distances: Marathon (8:00 AM), Half Marathon (8:00 AM), 10K (8:35 AM), 5K (8:00 AM)

Flat and fast USATF-certified courses along Oak Leaf Trail in an out-and-back format. Part of the "Run Wisconsin Race Series"—complete three participating races to conquer the series. Excellent for 50-state marathoners seeking a quality, lower-key event.

Registration: Marathon $99.99 (regular $150), Half $79.99 (regular $120), 10K $44.99, 5K $39.99
Time Limits: 5K: 1.5 hrs | 10K: 1:50 | Half: 3.5 hrs | Marathon: 6 hrs
Post-race: Bratwurst off the grill, Broken Bat Brewery beer, live band
Website: wisconsinruns.com/brewcityrun

Wisconsin Marathon (Kenosha)

Date: Saturday, April 25, 2026
Location: Downtown Kenosha (near Civil War Museum)
Distances: Marathon, Half Marathon, 5K

New for 2026: April race date, updated 5K route, and earlier early-start option (25 minutes before main start). The Lake Michigan shoreline course has been refined with no gravel sections. Finishers receive the distinctive "Big Cheese Medal."

Packet pickup: Available in Chicagoland, Milwaukee area, Kenosha, and race morning; mailing available
Lodging: Block at The Stella Hotel, downtown Kenosha
Website: wisconsinmarathon.com

Bosom Buddy 5K

Date: Saturday, April 25, 2026
Location: Cedarburg
Distances: 5K, 1 Mile

Breast cancer awareness charity run in historic Cedarburg.

Cream City 5K Run/Walk & Kellan's Kids Run

Date: Saturday, April 25, 2026
Location: Milwaukee (53227 area)
Distances: 5K Run/Walk, 3K Walk, 0.4K Kellan's Fun Run (ages 10 and under)

Raising awareness for organ, tissue, and eye donation since 2016. The dedicated kids run for ages 10 and under makes this a true family event. Early bird registration before January 4 is $30 (5K/3K); Kids Run is $15.

Website: creamcity5k.org

Golden Kettle Trail Series Begins

Date: April 25, 2026 (first race: McMiller)
Location: McMiller Ski Trails, Eagle
Distances: Short (~3 miles), Mid (~5 miles), Long (~12 miles), Golden Gauntlet (all three)

Seven trail races across Kettle Moraine from April through October. Unique features include stress-free start anytime between 7-11 AM, free craft beer from North Pillar Brewing Co., free Normatec boots session, and wooden finisher medals. Complete all seven for a custom BOCO bandana.

2026 Schedule:

• April 25: McMiller

• May 16: Blue Springs

• June 20: Greenbush

• July 11: Nordic

• August 8: Zillmer

• September 12: Oleson Cabin

• October 17: Scuppernong

Website: goldenkettletrailseries.com

Moonlight Meltdown 5K & Sunset Safari 10K

Date: Saturday, April 25, 2026
Location: Kyote's Bar and Grill, Belgium (Ozaukee County)
Distances: 5K (road), 10K (hybrid with 1.2-mile trail through Harrington Beach State Park)

The 10K Sunset Safari includes a scenic trail section through Harrington Beach State Park on snowmobile trail—rolling hills and wildlife encounters likely.

Benefits: Belgium Fire and Rescue, Rocket Academy, Snow Runners Ltd.
Website: moonlightmeltdown.com

Crazylegs Classic (Madison)

Date: Estimated Saturday, April 25, 2026 (typically last Saturday of April)
Location: Madison (Library Mall to Kohl Center)
Distances: 8K run (5 miles), 2-mile walk

This Madison institution—named after UW football legend Elroy "Crazylegs" Hirsch—draws 9,500-10,000+ participants and serves as the unofficial kickoff to spring in the capital. The post-race block party at Camp Randall Stadium features live music and beer. One of RRCA's "Great Races! Great Places!"

Registration: ~$35-50
Website: crazylegsclassic.com

Hometown Half Marathon & 5K/10K

Date: Sunday, May 3, 2026
Location: Milwaukee
Distances: 5K, 10K, Half Marathon, 1 Mile, Kids Dash

Youth pricing (12 and under) is just $17, with a dedicated Kids Dash for ages 10 and under (untimed). Designer shirts and custom medals included.

Website: runsignup.com/Race/WI/Milwaukee/HometownHalfMarathon5k10kMilwaukee

Ice Age Trail 50

Date: Saturday, May 9, 2026
Location: La Grange (Southern Kettle Moraine Forest)
Distances: 50 Mile, 50K, Half Marathon

One of the oldest continuously-running ultras in the country, this event traverses single-track dirt through dense deciduous forests, tall pines, rocky ridges, and open prairies featuring glacial formations like kettles, kames, and erratics. The 2026 races sold out in December 2024—join the waitlist at iceage50rd@gmail.com.

Insider tip: Registration opens December 14 with staggered times (50-mile at noon, 50K at 3 PM, half at 6 PM CT). Priority goes to veterans of 9+ Ice Age races and top 10 finishers.

Post-race: Excellent party with free food, beer, and live music
Website: iceagetrail50.com

Mother's Day Half Marathon, 10K & 5K

Date: May 10, 2026 (Mother's Day weekend)
Location: Urban Park, 1070 Michigan St, Milwaukee
Distances: 5K, 10K, Half Marathon

Every finisher receives a rose. Pacers available. Strollers allowed for walkers/joggers with signed waiver.

Website: wisconsinruns.com/milwaukeemothersday5k

Prickly Pine Jackpot 24-Hour Solo/Relay

Date: May 2-3, 2026
Location: Kettle Moraine State Forest, Dousman
Distances: 6-hour, 12-hour, 24-hour (solo); 12-hour, 24-hour (relay)

Three distinct loops—3 miles, 6 miles, 9 miles—on Ice Age Trail. Jackpot prizes for top finishers, camping available. Special belt buckles for 50+ mile completers (larger buckle for 100+ miles).

Website: runsignup.com/Race/WI/Dousman/PricklyPineJackpotHourSoloRelay

Cellcom Green Bay Marathon

Date: Sunday, May 17, 2026
Location: Start: Lambeau Field; Finish: Mike McCarthy Way (with lap around Lambeau!)
Distances: Marathon, Half Marathon, Marathon Relay, Half Marathon Relay, 5K, Kids Race

Expected participants: ~7,500. The course leaves the stadium district through Ashwaubenon, includes a scenic 6-mile stretch on Fox River Trail, and finishes with a lap around Lambeau Field—a bucket-list experience for Packers fans.

Time limit: 7 hours
Post-race: Tailgate-themed party with live band, pulled pork, chips, beer, and root beer
Website: cellcomgreenbaymarathon.com

Cedarburg Half Marathon & 5K

Cedarburg Half Marathon | 5K

Date: Saturday, May 23, 2026
Location: Cedarburg High School, W68 N611 Evergreen Blvd
Distances: Half Marathon, 5K, Youth 5K, NEW: RUCK Half Marathon (35# men/25# women)

Fast, certified, chip-timed flat bike path course. Benefits Camp Odayin at Camp Lutherdale (serves children with heart disease). Post-race flapjack breakfast, music, and awards. Stroller-friendly for 5K.

Packet pickup: Thursday May 21: 4-7 PM at Sahale Ale Works, Grafton; Friday May 22: 3-7 PM at Cedarburg High School Plaza
Website: cedarburghalfmarathon.com

Summer races: June through August

Fox Point Centennial 10K/5K

Date: Saturday, June 13, 2026
Location: Fox Point
Distances: 10K, 5K Run/Walk

Celebrating Fox Point's centennial—a true community celebration for all levels and families.

Kettle Moraine 100 Endurance Runs

Date: Saturday, June 13, 2026
Location: Nordic Trail Head, Whitewater
Distances: 100 Mile, 100K, 50K, 38-Mile Fun Run, 4-Person Team Relay

The crown jewel of Wisconsin ultramarathons. 100% trail (except road crossings), with 65 miles on the Ice Age National Scenic Trail through pinewoods, hardwood forests, and rolling prairie. This is a Western States 100 qualifier and part of the Midwest Grand Slam of Ultrarunning.

Registration (Early Bird): 100 Mile $336, 100K $205, 50K $169, 38-Mile $123, Team Relay $495
Cutoffs: 100 Mile: 30 hours; 100K: 29 hours
Pacer policy: 100 Mile pacers can start after 6:30 PM at Bluff, Nordic, Hwy 12, or Rice Lake; 100K pacers from 6:30 PM at Bluff; No pacers for 50K
Required: Wisconsin State Parks parking pass ($28 annual WI, $38 out-of-state)
Website: kettlemoraine100.com

Racine Lighthouse Run (48th Annual)

Date: Saturday, June 20, 2026
Location: Festival Park, 5 Fifth Street, Racine
Distances: 10-mile competitive (8:00 AM), 4-mile competitive (8:15 AM), 2 & 4-mile fun run/walk (8:20 AM)

One of Wisconsin's premier runs, featuring USATF-certified lakefront course through Racine's harbor and historic district. 2026 theme: Reef Lighthouse—each year's medal features a different lighthouse design (part of 4-year Lighthouse Legacy collection 2024-2027).

Registration deadline: June 7, 2026 for guaranteed shirt and medal; NO SAME DAY REGISTRATION
Benefits: YMCA Strong Kids Campaign
Post-race: Access to Racine Family YMCA Lakefront Branch facilities with race bib
Website: ymcaracine.org/lighthouse-run

Treat Trot Milwaukee

Date: Saturday, June 27, 2026
Location: Milwaukee
Distances: 5K, 10K, Half Marathon, Kids Dash, 1 Mile

Youth pricing (12 and under): $17. Kids Dash for ages 10 and under is untimed. Snacks at finish line.

Website: runsignup.com/Race/WI/Milwaukee/TreatTrotMilwaukee

Kenosha YMCA Firecracker 5K/1-Mile Fun Run

Date: Sunday, June 28, 2026
Location: Library Park, 711 59th Pl, Kenosha
Distances: 5K (chip-timed), 1 Mile Fun Run

USATF-certified scenic lakefront course with three water stations. Runners 10 and under need a "Running Buddy." Strollers allowed in 5K and 1 Mile; no dogs. "Last Chance" registration is $45 on June 28; NO race day registration.

Website: kenoshaymca.org/specialevents/firecracker

Storm the Bastille

Date: Friday evening during Bastille Days Festival, July 9-12, 2026 (typically 9 PM start)
Location: Cathedral Square Park, downtown Milwaukee
Distances: 5K run, 2-mile walk option

An evening/nighttime run through illuminated downtown Milwaukee as part of the city's largest Bastille Day celebration. Strollers welcome throughout the festival and even at the 5K. You can finish at the halfway point for a shorter walk if needed.

Registration: ~$35 early bird
Website: easttown.com

Dances with Dirt – Devil's Lake

Date: Saturday, July 11, 2026
Location: Devil's Lake State Park, Baraboo (~1.5 hours from Milwaukee)
Distances: 50 Mile, 50K, Marathon, Half Marathon, 10K

Dramatic geological terrain with ice age formations and what organizers call the "most dramatic aid station location in the world!" Part of the RF Events Dances with Dirt series.

Website: dwddevilslake.com

Color Run Milwaukee by Color Craze

Date: Saturday, July 11, 2026
Location: Milwaukee (venue TBD)
Distance: 3-5K untimed, non-competitive

Walk, run, or dance at your own pace—no winners or losers. Color stations throughout the course, mini music festival at finish, food vendors, photo OP screens, and color-setting station for shirts. Perfect for first-time runners and families.

Virtual option: "Paw Admission" (100% benefits pets)
Website: lunaticketing.com/events/milwaukee-color-run-by-color-craze

Portal Fish Day Run/Walk/Roll (Port Washington)

Date: Saturday, July 18, 2026 (41st Annual)
Location: Coal Dock Park, 146 S Wisconsin St, Port Washington
Distance: 5K Run, 5K Walk

Scenic route through Port Washington, Lake Michigan shoreline, Upper Lake Park, and Ozaukee County Interurban Trail. Registration opens Port Fish Day Festival—"World's Largest One Day Outdoor Fish Fry" with parade at 10 AM, carnival rides, four music stages, and fireworks.

Registration: $35 early, $40 race day (cashless only)
Benefits: Portal, Inc. (serving adults with intellectual and developmental disabilities)
Note: Service animals only—no pets at Coal Dock Park
Website: portalinc.org/portal-run-walk--roll.html

Badgerland Striders Firecracker Four

Date: July 4, 2026
Location: Hales Corners

A Fourth of July tradition from Badgerland Striders.

Adrenaline Races

Date: July 2026 (typically mid-July)
Location: Eisenbahn Trail, West Bend
Distances: 5K, 10K, Half Marathon, Full Marathon

USATF-certified Boston Qualifier on the scenic Eisenbahn Trail.

5K/10K Famous Racing Sausages Run/Walk

Date: July 2026 (TBD)
Location: American Family Field (Brewers Stadium)
Distances: 5K, 10K

Run alongside the famous racing sausages with the opportunity to run on the field. Benefits Brewers Community Foundation.

Cudahy Classic (Badgerland Striders)

Date: July 2026
Location: Cudahy

Mixed road, trail, and grass course offering 10-mile and 5-mile options.

Old Plank Sunset Half (Sheboygan County)

Date: August 9, 2026
Location: Elkhart Lake
Distance: Half Marathon

Scenic sunset half marathon in beautiful Sheboygan County lake country.

Madison Mini Marathon

Date: Saturday, August 8, 2026
Location: Memorial Union Terrace, Downtown Madison
Distances: Half Marathon (7:00 AM), 5K, Kids Run

Scenic route past Capitol Square, Dane County Farmer's Market, State Street, Camp Randall Stadium, Kohl Center, UW Arboretum, Picnic Point, and UW Campus. The "14th Mile Post-Race Party" at Memorial Union Terrace features live music, Lake Mendota views, and complimentary beer (21+). Expect a Bucky Badger appearance.

Website: madisonminimarathon.com

Bound for Boston Marathon & Half

Date: Sunday, August 23, 2026
Location: Menomonee Falls
Distances: Marathon, Half Marathon

Fast course specifically designed as a Boston Qualifier.

Strider Half Marathon (Badgerland Striders)

Date: Late August 2026 (typically before Labor Day)
Location: Estabrook Park, 4600 Estabrook Pkwy, Milwaukee/Shorewood
Distance: Half Marathon

Starts and finishes at Estabrook Park beer garden, running on shaded Oak Leaf Trail bike path. Post-race beer garden celebration with breakfast, beverages, and live music. Beautiful fall scenery.

Registration: ~$65-75 (Strider member discounts available)
Size: 500-1,000 participants
Website: badgerlandstriders.org

Fall races: September through November

Badgerland Striders 24-12-6 Hour Runs

Date: Saturday, September 5, 2026
Location: Delafield (1-mile lighted trail loop)
Distances: 24-hour, 12-hour, 6-hour

A timed ultra on a lighted loop course with excellent volunteer support. Accessible entry point for first-time ultra runners.

Dominican KnightRun (Whitefish Bay)

Date: September 19, 2026 (typically third Saturday of September)
Location: Dominican High School, 120 E Silver Spring Dr, Whitefish Bay
Distance: 5K

School fundraiser supporting Dominican High School—great for community supporters and alumni.

Hometown Half Marathon & 5K/10K (Fall)

Date: Saturday, September 19, 2026
Location: Milwaukee
Distances: 5K, 10K, Half Marathon, 1 Mile, Kids Dash

Second offering of the year. Youth pricing (12 and under): $17.

Milwaukee Beer Run 5K & .05K

Date: Sunday, October 4, 2026
Location: Bavarian Bierhaus/Heidelberg Park, Glendale
Distances: 5K (plus .05K for fun!)

Includes Gildan sweatshirt, collector's cup, complimentary craft beer or root beer (for kids/non-drinkers), chip-timed race, and entry to Milwaukee's Original Oktoberfest. Benefits Hunger Task Force.

Website: 414events.com/mkebeerrun

Milwaukee Lakefront Marathon Weekend

Date: Saturday-Sunday, October 3-4, 2026
Location: Start: Grafton (Marathon), Downtown Milwaukee (Half/5K); Finish: Veterans Park
Distances: Marathon (Sunday 7:00 AM), Half Marathon (Sunday 7:00 AM), 5K (Saturday 10:30 AM), "Own the Hoan" Challenge

Wisconsin's oldest and largest marathon, now in its 44th year. The point-to-point marathon course from Grafton features the only opportunity all year to run across the iconic Hoan Bridge. Over 40% of the course runs along Lake Michigan shoreline. Indoor waiting area near start line helps with cool October mornings.

Participant limits: Marathon: 2,500; Half Marathon: 3,500
Own the Hoan Challenge: Complete 5K on Saturday AND Half or Full on Sunday for a bonus third medal and extra swag
RRCA Regional Championship event
Benefits: This Time Tomorrow Foundation (cancer research)
Post-race: Celebration at Summerfest grounds with local food, music, awards
Website: milwaukeelakefrontmarathon.org

Insider tip: The half and full marathon courses share the first 10 miles—if you're debating distances, this gives you a chance to run with the marathon crowd before splitting off.

Hot Cider Hustle Half Marathon & 5K (Shorewood)

Date: Late October 2026 (typically October 25)
Location: Estabrook Park, 4600 Estabrook Pkwy
Distances: Half Marathon (USATF certified), 5K

Run Oak Leaf Trail through peak fall foliage with hot cider and caramel apples at the finish. Benefits Wisconsin Ovarian Cancer Alliance.

Website: allcommunity.events/wisconsin/shorewoodhotciderhustle

Lapham Peak Colorama Run/Walk

Date: October 2026 (typically first Saturday)
Location: Lapham Peak State Park, Delafield
Distances: 5K, 10K, Smokey Bear Fun Run

Wide, well-groomed ski and hiking trails showcase spectacular fall colors. The Smokey Bear Fun Run gives kids their own adventure.

Website: laphampeakfriends.org/colorama

Lakefront Discovery Run (Badgerland Striders)

Date: Saturday, October 31, 2026 (Halloween)
Location: Veterans Park, 1010 N. Lincoln Memorial Drive
Distances: 15K (9:05 AM), 5K (9:15 AM), FREE Kids Costume Race (8:45 AM)

Halloween costume theme with "Best Costume" awards, candy-laden aid stations, "Monster Mile" markers, and FREE BEER for all participants (costume or not!). Heated tent for post-race festivities.

Registration: 15K: $45-50 ($5 discount for Badgerland Striders members), 5K: $35-40
Packet pickup: Wednesday before race at Central Waters Brewing Taproom (1037 W. Juneau Ave)
Website: runsignup.com/Race/WI/Milwaukee/DiscoveryRun

Fast Eddie 50K/5K

Date: Mid-November 2026
Location: Lapham Peak, Delafield
Distances: 50K (five loops on Blue Loop), 5K

The 50K features approximately 3,610 ft elevation gain across five scenic woodland loops. Fundraiser for Little Warrior Foundation (childhood cancer).

Website: fasteddie50kand5k.com

Madison Marathon

Date: Sunday, November 15, 2026
Location: Start/Finish: Capitol Square, Madison
Distances: Marathon, Half Marathon, 10K, 5K

USATF-certified course weaving past lakes and UW-Madison campus landmarks. Warning: HILLY—numerous rolling hills including a tough climb in final miles through UW-Madison Arboretum and botanical gardens. Prize money available: $1,000 (1st), $500 (2nd), $250 (3rd).

Time limit: 6 hours
Registration: ~$208 (marathon)
Post-race: Beer for 21+, full recovery spread, free race photos
Website: madisonmarathon.org

Turkey Trails Milwaukee

Date: Saturday, November 21, 2026
Location: Cudahy
Distances: 1 Mile, 5K, 10K, Half Marathon, Kids Dash, Virtual Race

Multiple distance options with youth pricing. Get your turkey trot in before the holiday rush.

Registration: $17-$66
Website: runsignup.com/Race/WI/Cudahy/TurkeyTrailsMilwaukee

Milwaukee Turkey Trot 5K & 8K

Date: Thanksgiving Day, November 26, 2026
Location: Lincoln Memorial Drive/Veterans Park
Distances: 5K Run/Walk, 8K Run, Kids Dash (100m, ages 8 and under), 5K Kids Division Fun Run (ages 11 and under)

Part of the national "Thankful Turkey" event with 50,000+ participants nationwide. Features untimed 5K walk option and Cranky Al's donuts at the finish line. Strollers allowed for walkers/joggers (parent must sign waiver).

Registration: Typically $30-50 (early bird rates available)
Website: wisconsinruns.com/milwaukeeturkeytrot

Festival Foods Turkey Trot Milwaukee

Date: Thanksgiving Day, November 26, 2026
Location: American Family Field (Brewers Stadium)
Distances: 2-Mile Walk/Fun Run (untimed), 5-Mile Run (timed), 2-Mile Dog Jog

Open to all ages/abilities with Dog Jog option. Free Brewers game tickets for first 1,500 participants who pick up Wednesday before race. Strollers welcome (line up near back of group).

Benefits: Southwest & West Suburban YMCAs Annual Support Campaign
Website: festivalfoodsturkeytrot.com

Junior Woman's Club of Mequon-Thiensville Turkey Trot

Date: Thursday, November 26, 2026 (Thanksgiving)
Location: Village Park, Thiensville
Distance: 5K Run/Walk (chip-timed), Virtual option

Registration includes short-sleeve t-shirt (long sleeve upgrade $10). Medals for in-person chip-timed finishers. Great Thanksgiving tradition for families in Ozaukee County.

Packet pickup: Wednesday, November 25: noon-4 PM at Village Park; Race Day: 7:30-8:30 AM
Website: juniorsmt.org/turkey-trot.html

Jingle Bell Run Milwaukee

Date: Mid-November 2026
Distance: 5K
Registration: ~$30

Holiday-themed 5K run/walk benefiting the Arthritis Foundation.

Wisconsin Brewery Running Series

Dates: Multiple events monthly, April through November
Locations: Various Milwaukee breweries (Lakefront Brewery, Broken Bat Brewing, MobCraft, Westallion Brewing, and more)
Distance: Casual 5K-ish (untimed)

Each event includes craft brew, collector's pint glass or seasonal swag. Walkers welcome, no pressure, live music, food trucks, family-friendly atmosphere. 10% of proceeds go to local nonprofits.

Registration: ~$30
Website: breweryrunningseries.com/locations/wisconsin

Winter races continued: December

Bucks & Does 13.1 Pointer

Date: Early December 2026
Location: Nashotah Park, Waukesha County
Distances: Half Marathon, 10K, 5K, free Bambi Run for kids

Wood-chipped trails with some grassy sections, shaded by trees. Custom finisher "woodle" and free hot chocolate bar.

Last Call (Waukesha)

Date: December 7, 2026
Location: Waukesha
Distances: Half Marathon, 10K, 5K, Kids Run

Season-closing trail event bookending the "First Call" race in March.

Santa's Dash Away 5K

Date: Mid-December 2026
Location: Cedarburg
Distance: 5K

Holiday/Santa themed run through historic Cedarburg.

Run Santa Run 5K Milwaukee

Date: Mid-December 2026
Location: Veterans Park, 1010 N Lincoln Memorial Dr
Distance: 5K (timed, no awards)

Registration includes character-specific medals (Santa, Elf, or Polar Bear), long-sleeve character shirt (youth sizes available!), character hat and accessories, free digital race photos, one free beverage token, chocolate kisses, cookies, candy canes on course, and free hot cocoa. Costume contest and North Pole post-race party.

Registration: ~$40-50
Website: runsantarun5kmilwaukee.com

Run Into The New Year

Date: December 31, 2026
Location: Shorewood
Distances: 5K, 8K

New Year's Eve celebration run to close out the year.

Running clubs and training groups

For beginners and social runners

Milwaukee Running Group – OMG offers the most accessible entry point, with 18-20 runs per week, year-round. Their Monday 6:30 PM run at Lake Park Pavilion includes a Couch to 5K option. Just $5/year membership.

Badgerland Striders runs a free Stride to 5K Program for beginners and the Marathon Build-Up (MBU) program for those targeting the Lakefront Marathon. Membership: $25/year (family up to 6 members).

November Project Milwaukee offers completely free outdoor workouts Wednesday and Friday at 6:03 AM—high-energy group sessions that'll build your running and your social network simultaneously.

For serious training

Performance Running Outfitters (PRO) hosts free group runs from their four locations (Brookfield, Delafield, Third Ward, Shorewood). Their Monday 6 PM Lakefront Brewery run features half-priced pints after, and the Saturday 8:30 AM Brookfield run includes pancakes and coffee.

Run Ozaukee caters to runners maintaining weekly fitness goals, meeting in Cedarburg for 5-12 mile runs with aid every 2-4 miles.

For trail and ultra runners

Glacial Trail Running Group focuses specifically on trail running for all speeds. Badgerland Striders organizes multiple ultras including the John Dick Memorial 50K and 24-12-6 Hour Runs.

Wisconsin weather preparation tips

Spring (March-May): Expect anything. March races may see snow; May races may hit 70°F. Layer up and plan for mud on trails. The Trailbreaker and spring marathons often face 35-50°F temperatures.

Summer (June-August): Hot and humid, routinely 70-90°F. Start early (most races begin by 8 AM for good reason). Hydration strategy is critical—the Kettle Moraine 100 in June is particularly brutal. Train in the heat if racing in it.

Fall (September-November): The sweet spot. The Lakefront Marathon in early October typically sees ideal conditions (45-55°F). Fall foliage makes trail races spectacular. October trail races at Lapham Peak and Kettle Moraine are worth scheduling around.

Winter (December-February): Embrace it or run indoors. The Whitewalker Ultra and John Dick 50K expect snow and ice. The Pettit Indoor Marathon offers climate-controlled alternative. Yaktrax or similar traction devices are essential for winter trail running.

Universal tip: Wisconsin conditions change fast. Check forecasts the morning of, bring layers you can shed, and never count on the weather prediction from three days out.

Race series and challenges

Own the Hoan Challenge

Complete the Saturday 5K AND Sunday Half or Full Marathon at the Lakefront Marathon weekend (October 3-4, 2026) to earn a bonus third medal plus extra swag.

Wisconsin Trail Assail Series

Seven trail races from April through October across Waukesha County parks. Full series registration available; complete all seven for recognition.

Golden Kettle Trail Series

Seven Kettle Moraine trail races April through October with stress-free anytime starts, free craft beer, and wooden finisher medals. Complete all seven for custom BOCO bandana.

Badgerland Striders Club Championship

Points accumulated across designated races throughout the year in Men's/Women's Short, Long, and Ultra categories.

Run Wisconsin Race Series

Complete three participating races (including Brew City Marathon) to conquer the series.

Key registration resources

• RunSignUp: runsignup.com (most local races)

• Wisconsin Runs: wisconsinruns.com (comprehensive calendar)

• Active.com: active.com (national database)

• UltraSignUp: ultrasignup.com (trail and ultra events)

• Running in the USA: runningintheusa.com

• RunGuides: runguides.com/wisconsin/runs

• Badgerland Striders: badgerlandstriders.org

Final thoughts

The greater Milwaukee running scene offers something for everyone—from your child's first Kids Dash to your hundredth marathon, from flat lakefront paths to technical Kettle Moraine single-track. The community is welcoming, the beer is good, and the courses showcase Wisconsin's underrated natural beauty.

A few parting recommendations:

• Best beginner road race: Brew City 5K (flat, supportive, great post-race party)

• Best family event: Samson Stomp at Milwaukee County Zoo (zoo admission included!)

• Best destination half: Cedarburg Half Marathon (scenic, well-organized, charming town)

• Best bucket-list marathon: Milwaukee Lakefront Marathon (the Hoan Bridge!)

• Best introduction to trails: Wisconsin Trail Assail Series (walker-friendly, free kids 1K)

• Best ultra for first-timers: Arktos Winter Ultra (timed format, supported, manageable loops)

Register early for popular events—the Ice Age Trail 50 sold out months in advance, and the Milwaukee Marathon fills every year. Join a running club for training partners and insider knowledge. And most importantly, get out there. See you on the course.