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Date:
Sun, May 17, 2026 at 8:45 AM
Location:
Waukesha County, Wisconsin
53183
United States
OpenStreetMap Google Maps
Links:
runsignup.com
Tags:
2 Miles 3.1 Miles Run Trail

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

More races nearby

  • Lad Lake's Kettle Classic Bike- Walk- Run Event 2026 [ladlake.org] [Register at runsignup.com]

    Sat, Jun 20, 2026 at 6:45 AM

    Description

    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.

    6.2 km
    W350 S1401 Waterville Road, Waukesha County, Wisconsin, 53118, United States
    OpenStreetMap Google Maps

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

  • Prowl The Peak [finishers.com]

    Thu, Aug 06, 2026

    6.6 km
    Delafield, Wisconsin, United States
    OpenStreetMap Google Maps

    Run Trail

  • National Sweetest Day [runsignup.com]

    Sat, Oct 17, 2026 at 8:00 AM

    Description

    National Sweetest Day Run 🍬❤️

    Celebrate National Sweetest Day by doing something truly sweet for yourself and those you care about—join us for a fun run or walk! Whether you’re running solo, with...

    National Sweetest Day Run 🍬❤️

    Celebrate National Sweetest Day by doing something truly sweet for yourself and those you care about—join us for a fun run or walk! Whether you’re running solo, with friends, or sharing this special day with a loved one, this event is all about spreading joy, kindness, and a little bit of sweat.

    Event Highlights:

    • Distance Options: 5K, 10K, or Half Marathon—something for everyone!

    • Sweet Treats: Enjoy post-race goodies to reward your hard work.

    • Scenic Course: A beautiful trail surrounded by nature—perfect for a relaxing run or walk.

    • For Everyone: Bring your sweetest someone, your bestie, or the whole family!

    National Sweetest Day is about showing kindness and love, and there’s no sweeter way to do that than by spending time together outdoors. So grab your running shoes, spread some cheer, and make this Sweetest Day one to remember! ❤️


    8.6 km
    W330 N5113 County Road C, Delafield, Wisconsin, 53058, United States
    OpenStreetMap Google Maps

    3.1 Miles 6.2 Miles 13.1 Miles Fun Run Run Trail Walk

  • Among the Trees [pricklypineultrarunning.com] [Register at runsignup.com]

    Sat, Oct 31, 2026 at 6:00 AM

    Description

    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

    8.3 km
    S57 W35510 Co Road ZZ, Waukesha County, Wisconsin, 53118, United States
    OpenStreetMap Google Maps

    50k 100k Run Trail Ultra

More races nearby →

Local running group

  • Buena Tierra Run Club Group 38 km
    [buenatierramke.com] [runningcrews.com] - Facebook - Instagram

    Founded in Milwaukee in late 2023, Buena Tierra Run Club has rapidly grown from a small group of seven to a vibrant community. Inspired by Patrick’s experience running through Chicago’s Pilsen neighborhood, the group was formed to create a Latino-centered space in Milwaukee’s Southside where running encourages physical and mental well-being. Meeting weekly, their runs connect participants to local streets and landmarks that celebrate Latino heritage and Milwaukee’s diverse urban landscape. Open to everyone but focused on Latino identity, Buena Tierra promotes inclusive, laid-back runs that foster camaraderie and support beyond just the pavement.

    Community Run

    Contact: [email protected]

    Milwaukee, Wisconsin, United States
    OpenStreetMap Google Maps
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