7 events in Waukesha County, Wisconsin

From big races to Saturday morning group runs—find trail running events and connect with the local endurance sports community.

• Golden Kettle Trail Series [goldenkettletrailseries.com] [Register at runsignup.com]
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  Sat, Apr 25, 2026 at 7:00 AM

  Description

  SERIES SCHEDULE

  1. McMiller | April 25, 2026

  2. Blue Springs | May 16, 2026

  3. Greenbush | June 20, 2026

  4. Nordic | July 11, 2026

  5. Zillmer | August 8, 2026

  6. Oleson Cabin | September 12, 2026

  7. Scuppernong | October 17, 2026

  For complete race details please visit the website @ www.goldenkettletrailseries.com

  Trail

  Waukesha County, Wisconsin, 53119, United States
  OpenStreetMap Google Maps
• Prickly Pine Jackpot 24 Hour Solo/Relay [runsignup.com]
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  Sat, May 02, 2026 at 8:00 AM

  Description

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  Looking for an all night running party?

  Join us for the Prickly Pine 24-Hour Solo/Relay race in the beautiful Kettle Moraine State Forest! With a variety of time options—6-hour, 12-hour, 24-hour, and...

  Looking for an all night running party?

  Join us for the Prickly Pine 24-Hour Solo/Relay race in the beautiful Kettle Moraine State Forest! With a variety of time options—6-hour, 12-hour, 24-hour, and a 4-person 24-hour relay—you can choose the challenge that suits you. Not a fan of repeating the same loop? We’ve got you covered with three unique loops: Loop #1 (3 miles), Loop #2 (6 miles), and Loop #3 (9 miles). You decide which loop to tackle each time, and every completed loop counts toward your total mileage!

  Jackpot Prizes for the top 5 finishers in the solo event and top team in the relay.

  For each 24-hour solo participant and relay team, 25% from your registration fee will be added to the solo and relay Jackpot, respectively.

  Solo competitors – 1st place is awarded based on the total miles of completed loops. If you don't finish the loop you're on when time runs out, that loop won't count toward your total. In the event of a tie, the prize money for the tied positions will be combined and evenly split. For example, if two runners tie for first place, the 1st and 2nd place prize amounts are combined and shared. If there’s a 3-way tie, the prizes for 1st, 2nd, and 3rd will be pooled and divided equally.

  1st Place = 50% of the Jackpot

  2nd Place = 30% of the Jackpot

  3rd Place = 10% of the Jackpot

  4th Place = 5% of the Jackpot

  5th Place = 5% of the Jackpot

  Relay Jackpot

  The winning team will take home the entire Jackpot! In the event of a tie, each team will select one runner to compete in a final, winner-takes-all lap on the 3-mile loop.

  Race Course Description

  Experience the stunning pinewoods of the Southern Kettle Moraine Forest and the beauty of the Ice Age Trail. Our course takes you through loops that explore every section of the Scuppernong Trails, including some of the highest elevations on the Kettle course.

  All runners will start and finish at the DJ Mackie Picinic Area.

  24 HR Solo & Relay runners will start at 10:00 AM Saturday morning

  12 HR Solo & Relay runners will start at 8:00 AM Saturday morning and finish at 8:00 PM Saturday night.

  6 HR runners are welcome to start with the 24 HR runners at 10:00 AM but are allowed to start at any time. There is a cutoff of 10:00 AM Sunday morning for all runners, so the last 6 HR start time would be 4:00 AM.

  For more details on the course click on the link below for our Prickly Pine Ultra Running website.

  Military Discount code - TYforyourservice

  Race Swag

  6-hour Racers

  24 oz Easy Squeeze Sports Bottle & Finisher Metal

  12-hour Racers

  24 oz Easy Squeeze Sports Bottle, Cooling Towel & Finisher Metal Also Runners who complete over 50 miles receive a 50-mile Belt Buckle

  12-Hour Relay Racers

  24 oz Easy Squeeze Sports Bottle, Cooling Towel & Finisher Metal

  24-hour Racers

  Duffle Bag, 24 oz Easy Squeeze Sports Bottle, Cooling Towel & Finisher Metal Also Runners who complete over 50 miles receive a 50-mile Belt Buckle.

  24-hour Relay Runners

  24 oz Easy Squeeze Sports Bottle, Cooling Towel & Finisher Metal Also Runners who complete over 50 miles receive a 50-mile Belt Buckle

  Parking

  Wisconsin State Forest parking pass required for parking at our race. Please help support our state parks and click on the link below to purchase.

  https://dnr.wisconsin.gov/topic/parks/admission

  If you need to purchase a parking sticker the day of the event, they are available for purchase at the Ottawa Lake Park entrance. Located below at the address below

  S59 W36530 County ZZ

  Dousman, WI 53118

  Also - The first 30 24 Hour solo and relay racers to register will have a reserved 12'x12' gear drop spot near the start/finish line.

  Camping

  There will be a designated camping area near the start/finish line for the 24 Solo and Relay racers at no charge.

  Camping is available on connected trails to the race via the link below. (Loop 3 is the closest to the start/finish).

  Pinewoods Campground

  Questions?

  Check out our Prickly Pine Ultra Running Website and see more upcoming races as well!!!

  https://www.pricklypineultrarunning.com/

  Relay Run Trail Ultra

  S57W35510 Cty Rd ZZ, Waukesha County, Wisconsin, 53118, United States
  OpenStreetMap Google Maps
• Wisconsin Pickle Run [runsignup.com]
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  Sun, May 17, 2026 at 8:45 AM

  Description

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  Introducing: The Pickle Run – Wisconsin’s Only Dill-ightful Race! 🥒

  What’s in Store:

  • Location: The beautiful, paved Glacial Drumlin Trail in Wales, WI.

  • Scenic Spring Views: Take in the stunning...

  Introducing: The Pickle Run – Wisconsin’s Only Dill-ightful Race! 🥒

  What’s in Store:

  • Location: The beautiful, paved Glacial Drumlin Trail in Wales, WI.

  • Scenic Spring Views: Take in the stunning sights of Kettle Moraine while you run and crunch on some pickles!

  This fun and unique race combines endurance with Wisconsin’s love of pickles. Whether you’re in it for the run, the views, or the pickles, it’s bound to be a dill-lightful experience!

  Course map

  Don’t miss out—it’s the ONLY pickle run in Wisconsin!

  Wales Community Park

  500 S Brandybrook Rd, Wales, WI 53183

  2 Miles 3.1 Miles Run Trail

  Waukesha County, Wisconsin, 53183, United States
  OpenStreetMap Google Maps
• Lad Lake's Kettle Classic Bike- Walk- Run Event 2026 [ladlake.org] [Register at runsignup.com]
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  Sat, Jun 20, 2026 at 6:45 AM

  Description

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  Join us at our annual Kettle Classic, Bike Walk Run Event

  Join us for the Kettle Classic, Lad Lake’s annual Bike • Walk • Run event celebrating community, movement, and impact. This family-friendly...

  Join us at our annual Kettle Classic, Bike Walk Run Event

  Join us for the Kettle Classic, Lad Lake’s annual Bike • Walk • Run event celebrating community, movement, and impact. This family-friendly day brings people together to support more than 1,100 youth and families across Wisconsin through Lad Lake’s trauma-informed, evidence-based programs focused on mental health, healing, and education.

  Whether you’re cycling through the scenic Kettle Moraine, tackling the 5K Trail Challenge, walking at your own pace, there’s an option for everyone. Enjoy music, kids’ activities, a delicious barbecue lunch, and great company all while making a meaningful difference.

  Your participation powers life-changing support for youth and families across Wisconsin.

  Schedule|Event Experiences

  Important Note: All events must be completed by 12:45 PM.

  Bike Rides

  Choose from three non-competitive routes through the scenic Kettle Moraine, all with SAG support and rest stops.

  100K Ride

  Start: 7:00 AM (Line up at 6:45 AM)

  15-mile & 30-mile Rides

  Start: 9:00 AM (Line up at 8:45 AM)

  5K Trail Run / Walk – Challenge Event

  Start Time: 9:30 AM (Line up at 9:15 AM)

  🏅 Awards:

  The top 3 male and female finishers will receive a custom medal immediately after finishing.

  2-Mile Walk ((Line up at 9:45 AM)

  Start Time: 10:00 AM

  Not interested in a 5K? Join us for a relaxed 2-mile walk and enjoy the scenic views of our campus. A great option for families and anyone looking to support a great cause at their own pace.

  🌍 Go Virtual

  Can’t attend in person? Participate from anywhere!

  Bike, walk, or run wherever you are—on a treadmill, around your neighborhood, or even in your living room. Your virtual participation still supports Lad Lake’s mission and makes a real difference.

  Event Day Fun

  • Music

  • Delicious barbecue lunch (11am- 1:00pm)

  • Kids’ activities

  • Free raffle drawing

  • Learn more about Lad Lake and our impact

  Registration Details

  Advance registration is strongly encouraged

  Race-day registration is electronic only

  T-Shirt Deadline: Friday, May 29

  👉 Please consider making a donation above your registration fee, or becoming a fundraiser to further support youth and families served by Lad Lake.

  5k 15 Miles 30 Miles 62 Miles Cycling Run Trail Virtual Walk

  W350 S1401 Waterville Road, Waukesha County, Wisconsin, 53118, United States
  OpenStreetMap Google Maps
• HELIOS 6/12/20 HOUR ULTRA [goldenkettletrailseries.com] [Register at runsignup.com]
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  Sat, Oct 10, 2026 at 11:59 AM

  Description

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  October 10th-11th, 2026 | Eagle, Wisconsin

  6 / 12 / 20 Hour Ultra Run (Solo Runner or Relay team of up to 4)

  Join us for the inaugural 6-, 12- or 20-Hour FALL Ultra in the Southern Kettle Moraine...

  October 10th-11th, 2026 | Eagle, Wisconsin

  6 / 12 / 20 Hour Ultra Run (Solo Runner or Relay team of up to 4)

  Join us for the inaugural 6-, 12- or 20-Hour FALL Ultra in the Southern Kettle Moraine Forest. Complete as many loops as possible during your selected timeframe of 6, 12 or 20 hours.

  This race is capped at 150 runners. Signup now before it sells out!

  The goal of this race is to complete as many loops as possible during your selected timeframe of 6, 12 or 20 hours. You may race as a solo ultra runner or as a relay team of up to 4 people. You will choose between three of the McMiller Trail loops - approximately 3, 5 or 6 miles.

  Run Trail Ultra

  S104 W38754 County Rd NN, Waukesha County, Wisconsin, 53119, United States
  OpenStreetMap Google Maps
• Among the Trees [pricklypineultrarunning.com] [Register at runsignup.com]
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  Sat, Oct 31, 2026 at 6:00 AM

  Description

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  Race Description

  Join us on October 31th, 2026, for a scenic run through the Southern Kettle Moraine Forest on the historic Ice Age Trail. Participants can choose between 100k and 50k distances. Each...

  Race Description

  Join us on October 31th, 2026, for a scenic run through the Southern Kettle Moraine Forest on the historic Ice Age Trail. Participants can choose between 100k and 50k distances. Each finisher will have the opportunity to brand their wooden medal on-site, with the option to have their finishing time burned on the back. Enjoy the stunning fall colors and be part of this memorable event.

  100k Elevation - 6,493

  50k Elevation - 2,221

  Race Course

  The 100k and 50 races will both start at DJ Mackie Campground, situated on the Scuppernong trails. Participants will navigate the green loop of the Scuppernong trail and proceed to join the Ice Age Trail westward to Emma Carlin. The 50k runners will turn around at Emma Carlin, while the 100k runners will continue on to Whitewater. Full maps with elevations along with aid station details will be posted on www.pricklypineultrarunning.com.

  100k Start time 6:00 AM / 11:00 PM Cutoff

  50k Start Time 8:00 AM / 11:00 PM Cutoff

  Aid Stations 100k

  HWY 67 - 8 miles / Emma Carlin - 16.7 miles / HWY 12 - 30.8 miles / Whitewater 34.9 (Turnaround)

  HWY 12 - 39 miles /Emma Carlin - 53.1 miles / HWY 67 - 61.8 miles / Finish - 64.4 miles

  Aid Stations 50k

  HWY 67 - 8 miles / Emma Carlin 16.7 miles (Turnaround) / HWY 67 - 25.4 / Finish 31.1

  Items - (Water / Tailwind / PB & Js / Pickles / Bananas / Potato chips / Sour Patch Kids)

  Pacers - Pacers may join the 100k runners anytime at or after the turnaround at Whitewater

  Military Discount code - TYforyourservice

  50k 100k Run Trail Ultra

  S57 W35510 Co Road ZZ, Waukesha County, Wisconsin, 53118, United States
  OpenStreetMap Google Maps
• ARKTOS [http:///www.goldenkettletrailseries.com/arktos] [Register at runsignup.com]
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  Sat, Feb 27, 2027 at 9:59 AM

  Description

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  February 28th-March 1st | Dousman, Wisconsin

  6 / 12 / 24 Hour Ultra Run (Solo Runner or Relay team of up to 4)

  The original 6-, 12- or 24-Hour Winter Ultra in the Southern Kettle Moraine Forest....

  February 28th-March 1st | Dousman, Wisconsin

  6 / 12 / 24 Hour Ultra Run (Solo Runner or Relay team of up to 4)

  The original 6-, 12- or 24-Hour Winter Ultra in the Southern Kettle Moraine Forest. Complete as many loops as possible during your selected timeframe of 6, 12 or 24 hours.

  WE CAP THIS RACE AT 160 runners. IT WILL SELL OUT EARLY - signup now before spots are full.

  For complete race details please visit www.goldenkettletrailseries.com/arktos

  Run Trail Ultra

  S58 W35820 County Rd ZZ, Waukesha County, Wisconsin, 53118, United States
  OpenStreetMap Google Maps