Pleasant Prairie, Wisconsin

Looking for the best chillin 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 Chillin Spots in and near Pleasant Prairie

  • 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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  • South Milwaukee, Wisconsin

    Seven Bridges Trail in Grant Park

    4.2
    0.98 mi / 72 ft gain
    Placed along the Lake Michigan lakeshore in Grant Park about 10 minutes south of Downtown Milwaukee, Seven Bridges Trail offers beautiful scenery that seems like something out of a fairy tail. The trail begins at the the Covered Bridge Entrance which you can access by entering off of Grant Park D...
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  • Cudahy, Wisconsin

    Experience a Sunrise at Sheridan Park

    5.0
    Sheridan Park is home to one of the most beautiful, stunning and scenic sunrises in Wisconsin. Located about 10 minutes south of downtown Milwaukee, this location is accessible by hiking about 10 minutes from your parking location. Follow the winding path down to the beach and you'll find abandon...
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  • Milwaukee, Wisconsin

    Take a Stroll around the Lagoon at Wilson Park

    2.2 mi
    Whether your looking to relax or are going for a run, Wilson Park is a perfect place for whatever recreation you desire. The lagoon is one of the best in the city and offers some beautiful scenery during the evening hours. After taking in the lagoon, head through the trails around the park to exp...
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  • Milwaukee, Wisconsin

    Explore the Abandoned Solvay Coke & Gas Complex

    2.0
    1 mi
    To access the complex, head south from downtown Milwaukee along 1st St. Once you reach Greenfield Ave., turn left heading East. You'll pass under a concrete train bridge before seeing an open field on your right. Park your car along the street and head south past the crumbled brick of another for...
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  • Milwaukee, Wisconsin

    Photograph Jones' Island

    Urban explorers, meet your new favorite spot. Located right outside of downtown Milwaukee, Jones' Island is home to a water reclamation facility, road salt storage, milorganite, the Port of Milwaukee and more. But us explorers view it as a desolate haven ready to become our canvas. Train tracks a...
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  • Milwaukee, Wisconsin

    ​Explore the Milwaukee Domes

    5.0
    Officially called the Mitchell Park Horticultural Conservatory, this is a great stop to learn about some plants and take some photographs.  You can even catch live music or a light show!    Location: Mitchell Park Horticultural Conservatory - 524 S. Layton Boulevard, Milwaukee, WI 53215 Admission...
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  • Milwaukee, Wisconsin

    Hike the Hank Aaron and Oak Leaf Trails in Lakeshore SP

    4.3
    1.7 mi / 0 ft gain
    Lakeshore State Park is kind of considered a hidden gem. While yes, it's right along the Milwaukee lakefront, people don't realize just how nice and beautiful it is! This urban state park features two loops (the Hank Aaron and Oak Leaf) that total 1.7 miles. To access the park, you can either par...
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  • Milwaukee, Wisconsin

    Beach day at Bradford Beach

    There are not many sandy beaches in the lovely state of Wisconsin.  This might be the best one.  If you are from Wisconsin, you also might consider Lake Michigan an ocean when you are craving a real ocean.  And it comes close!  Even though it’s not on a real ocean, this beach has it all. There’s ...
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  • Milwaukee, Wisconsin

    Lake Park

    4.5
    1 mi / 100 ft gain
    This park has it all! Lake Park Bistro, golfing, hiking, a lighthouse, hiking trails, biking trails, and picnic spots galore!  Take the Oak Leaf Trail throughout the park to make a loop around all of the main landmarks in this historic park!  There are many things to see in this park! Multiple ...
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  • Evanston, Illinois

    The Lakefill

    5.0
    From the Northwestern University campus, head to the Ryan Center for the Musical Arts to access the southern-most section of The Lakefill. If driving, parking is usually available nearby on Sheridan Road, to the southwest of The Lakefill. Once at the Ryan Center, take the pedestrian bridge on the...
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  • Shorewood, Wisconsin

    Explore Atwater Park

    0.5 mi / 200 ft gain
    One of Milwaukee's truly hidden gems, this beach is right off of Capitol Drive and approximately 50 stairs down from the bluffs to the shoreline!  You can park anywhere on the road (Lake Drive) and be a short walk to the main overlook. This beach has many jetties that go out into the water which ...
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  • Des Plaines, Illinois

    Watch the Sunset at Axehead Lake

    In a large city, it's nice to be able to find pockets of nature oasis amidst the chaos. It's great to come here with a journal or sketchbook and pass the time while watching the sunset. Fishing is available at this lake and there is a forest preserve that has a couple small trails. 
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  • Pewaukee, Wisconsin

    Pewaukee Lake Beach Pier

    Enjoy breathtaking views on one of the few local lakes in SE Wisconsin to see sunset all year round! From September to March the sun lines up perfectly across the lake, otherwise the sun sets to the north (right) of the beach in the summertime. There are plenty of spots to sit and watch as the su...
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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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  • Fox Point, Wisconsin

    Hike the shore of Lake Michigan at Doctor's Park

    2 mi / 100 ft gain
    This park has it all. There is ample parking, full bathrooms, and picnic areas. The trail starts right at the parking lot and there are two different paths you can take: 1.) Follow the paved path down toward the lake on the north side of the parking lot 2.) Walk straight from the parking lot acro...
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