Waukesha, Wisconsin

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

Top Chillin Spots in and near Waukesha

  • Pewaukee, Wisconsin

    Catch a Sunset on 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

    Hike the Kettle View Trail at Lapham Peak

    5.0
    5.8 mi
    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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  • Milwaukee, Wisconsin

    ​Explore the Milwaukee Domes

    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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  • Hartford, Wisconsin

    Hike to Loew Lake

    5.0
    3 mi
    Starting from county rd K you turn in on Emerald Drive . at the start of Emerald drive is an old and tiny cemetery. Travel all the way on Emerald drive until you reach a sign that says Emerald Lot which is where you park, you can go left or right along the Ice age trail that crosses all across WI...
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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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  • Hubertus, Wisconsin

    Scenic Tower at Holy Hill

    4.5
    1 mi / 200 ft gain
    The scenic tower at Holy Hill is one of the highest accessible peaks in the area if you do not own a drone! The views are endless! There are many glacial drumlins, bluffs, and hills everywhere that fill the eye to meet the horizon. You can park in any of the main parking lots at Holy Hill. You w...
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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

    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

    Explore Lake Park

    4.0
    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 ra...
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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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  • 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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  • South Milwaukee, Wisconsin

    Hike the Seven Bridges Trail in Grant Park

    5.0
    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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  • 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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  • Grafton, Wisconsin

    Hike the Lion's Den Gorge Loop

    4.7
    1.8 mi
    Lion's Den Gorge is a gorgeous nature preserve featuring a variety of unique nature scenes. The park includes massive bluffs, sand dunes, forests, creeks and bridges, hiking trails and stunning vistas of the Lake Michigan shoreline. The preserve is 72 acres and is located in the town of Grafton, ...
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