Pleasant Prairie, Wisconsin

Looking for the best running in Pleasant Prairie? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Pleasant Prairie. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Running Spots in and near Pleasant Prairie

  • Lake Villa, Illinois

    Hike Hastings Lake LCFP

    5.0
    2.37 mi / 88 ft gain
    Park in the lot off of Butler Lane (see map) to access the trail. This trail is open year round, is dog-friendly, and offers a variety of activities. In the winter, bring your snow gear!
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  • Vernon Hills, Illinois

    Big Bear and Little Bear Lake Loop

    1.74 mi / 43 ft gain
    Big Bear and Little Bear Lake Loop is a loop trail that takes you by a lake located near Vernon Hills, Illinois.
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  • Ringwood, Illinois

    Hike the Glacial Park Loop Trail

    2.3 mi / 216 ft gain
    Glacial Park is located in McHenry County Conservation District, near Richmond, Illinois. The park features prairies, a flowing river, and over 40 endangered plant and animal species. The park is open for hikers, horseback riders, fishers, and those wishing to canoe. Glacial Park is part of the H...
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  • Deerfield, Illinois

    Hike the Prairie Wolf Slough Loop

    3.0
    1.01 mi / 9 ft gain
    Park in the lot off of half day road (see map) to access the trail. Accessible year round, great for all skill levels, and dog-friendly.
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  • Northfield, Illinois

    Bike the Skokie Lagoons North Loop

    3.0
    4.5 mi
    Starting at Tower Road, the path follows the bridge east to Forest Way Drive. The path mostly follows the road, and the shoreline of the lagoons up to Dundee Road, where you turn back West. Once across the bridge, you then head south on the paved trail back towards Tower Road. The Route is marked...
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  • Waukesha, Wisconsin

    Bike or Run the Glacial Drumlin Trail (Waukesha to Wales Segment)

    5.0
    14 mi
    Your journey begins at the Fox River Sanctuary and E.B. Shurts Environmental Education Center at 810 College Avenue in Waukesha, Wisconsin. Parking is plentiful, and you'll find restrooms and bubblers (or, water fountains to you non-natives) available seasonally. The Glacial Drumlin Trailhead is ...
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  • Whitewater, Wisconsin

    Nordic Trail Blue Loop

    5.0
    9.05 mi / 732 ft gain
    Nordic Trail Blue Loop is a loop trail that takes you by a lake located near Whitewater, Wisconsin.
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  • Dousman, Wisconsin

    Ice Age Trail: Scuppernong

    6.8 mi / 545 ft gain
    Ice Age Trail: Scuppernong is a point-to-point trail where you may see beautiful wildflowers located near Dousman, Wisconsin.
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  • Delafield, Wisconsin

    Kettle View Trail

    5.0
    5.88 mi / 1093.18 ft gain
    Head 30 minutes west from Milwaukee along I-94 and you'll find yourself in the quaint town of Delafield, WI. Head south down Genesee St. for a half mile and you'll see the entrance to Lapham Peak, part of the Kettle Moraine State Forest. Once there, you can head up the winding road to the parking...
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  • Wayne, Illinois

    Pratts Wayne Woods Loop Trail

    4.0
    1.01 mi / 33 ft gain
    Pratts Wayne Woods Loop Trail is a loop trail that is good for all skill levels located near Wayne, Illinois.
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  • Chicago, Illinois

    Run Chicago’s Lakefront Trail

    5.0
    6.7 mi
    Chicago – the third largest city in the US and home to the deep dish pizza – doesn’t exactly scream “outdoorsy.” In reality, there is much more to Chicago than skyscrapers; there are dozens of parks, outdoor music venues, and the city is right on Lake Michigan, making it very easy on the eyes. Be...
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  • Nashotah, Wisconsin

    Hike the Grass and Forest Lake Loop at Nashotah Park

    3 mi / 200 ft gain
    Park Hours: 6AM to 10PM  Official Nashotah Park Website Excerpt from the website: Nashotah Park is a 444-acre park nestled among rolling hills, woodlands, wetlands, and grasslands that offer habitat for deer, waterfowl and a variety of songbirds. Nature trails lead through easily identifiable lan...
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  • Chicago, Illinois

    Lakeshore Path: North Ave Beach to Navy Pier

    1.84 mi / 72 ft gain
    Lakeshore Path: North Ave Beach to Navy Pier is a point-to-point trail that takes you past scenic surroundings located near Chicago, Illinois.
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  • Chicago, Illinois

    Millennium Park

    5.0
    0.63 mi / 26 ft gain
    Millennium Park in Chicago, which opened in 2004, is a world-class public space featuring iconic landmarks like Cloud Gate (“The Bean”) and the Crown Fountain. Originally a rail yard, the park was transformed as part of a larger effort to revitalize the downtown area. It spans 24.5 acres and serv...
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  • Chicago, Illinois

    Luire Garden

    0.18 mi / 10 ft gain
    Visiting Chicago I was on a mission to find a great outdoors spot to be in. This definitely fulfilled my goal of finding a beautiful garden to hangout in! There are plenty of different paths and areas to explore just within the city! Location Located in Millennium Park it will be easy to find,...
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  • Brookfield, Illinois

    Salt Creek Greenway Trail

    13.99 mi / 551 ft gain
    This trail is almost 7 miles one-way (14 miles out-and-back) of paved path, makes for an ideal biking (especially those of us with road bikes), skating, and even running path. The trail runs out-and-back along the Salt Creek in Brookfield, IL. The trailhead is right near the Brookfield Zoo (for a...
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