Wisconsin

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

Top Chillin Spots in and near Wisconsin

  • Washington, Wisconsin

    Bike Washington Island

    15 mi / 100 ft gain
    It will take a drive and a ferry to get here, but once you do you’ll want to rent a bike to explore the island in earnest. You’ll have time to cycle around the whole island, with side trips to beaches, frontier houses, and picnic spots or small cafes. To get to Washington Island, drive north on H...
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  • Colfax, Wisconsin

    Hike the Hoffman Hills Outer Loop

    4.2 mi / 577 ft gain
    Hoffman offers convenient parking; there is one large lot, and one for overflow. There are trails that are easy, moderate, and difficult.  All of the trails however, are uphill.  Most of them end at the viewing tower, which showcases Wisconsin, and the beauty that goes along with it.  A very rewa...
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  • Dresser, Wisconsin

    Hike the Osceola Bedrock Glades Loop

    2.2 mi / 59 ft gain
    Just a short hike to the waterfall, this is a great spot to pull off on your way to the Park with many other trails to spend a whole day on if you wish to stay off the beaten path.  Getting there:  Going North through Osceola on HWY 35 Turn left on River Rd (county Rd S) For 1 mile. There is a sm...
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  • North Freedom, Wisconsin

    Hike the Natural Bridge State Park Loop

    3.0
    3.5 mi / 566 ft gain
    Located in Wisconsin’s Driftless Region, Natural Bridge State Park includes 530-acres of oak and hardwood trees, small prairie remnants with grasses and cacti, ferns, and the rare goldenrod and purple cliffbrake. Wildlife in the park includes turkey vultures, pileated woodpeckers, and bald eagles...
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  • Poynette, Wisconsin

    Float on the Wisconsin River at Camp Rest Park

    If you come on a weekend expect there to be a crowd, but there is plenty of space for everyone.  You can hang out on the shore, float in the water on an inflatable floatie, kayak, canoe, or spread out on one of the many sand bars close by.  Depending on the time of year and level of the water, yo...
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  • W4851 High Cliff Road, Wisconsin

    Hike the Limestone Bluffs at High Cliff

    4.0
    0.8 mi
    High Cliff State Park has some great hiking and cool spots throughout the park, but something that isn't on the map is located right next to the Observatory Tower atop of the bluffs. From the main parking lot area, left of the observatory tower, there is an old stone entrance behind a wooden fenc...
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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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  • Boulder Junction, Wisconsin

    Camp at Crystal Lake Campground

    An incredibly popular campsite that surrounds Crystal Lake and that offers access to Muskellunge Lakes. The State Park off County Road N, near Sayner, is great for bike enthusiasts and families looking to dip their paddles into the blue waters. Prime campsites include high, dry ground with level ...
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  • Madison, Wisconsin

    Explore the University of Wisconsin Arboretum

    It is filled with effigy mounds, thousands of plant and animal species, and unlimited places to explore.  You can run, hike, bike, and even drive through the Arboretum.  There is a visitor center and you can host an event here.  Trail info  One of my favorite trails is in the Grady Tract area nea...
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  • Mellen, Wisconsin

    Red Granite Falls

    2.46 mi / 246 ft gain
    Starting at the parking lot for Loon Lake, follow the signs for Red Granite Falls across a grassed yard and into the woods. The trail is a wide, well-maintained gravel trail that creates a figure-eight loop as it crosses itself twice. Halfway along the trail (regardless of which loop direction y...
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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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  • Eau Claire, Wisconsin

    Big Falls County Park

    5.0
    When I went in 2019 it was free, but their website says there is a fee now. Hike around for an hour or so and then have a picnic. I went around 6pm after work one day and had a wonderful time.  We only saw about a dozen people and during our picnic we had the place to ourselves!  This is a 135 a...
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  • Wausau, Wisconsin

    Explore Bluegill Bay County Park

    Take Cloverland or Parrot Avenue off the hustle of Rib Mountain Drive in the Southern community of Wausau to enjoy access to the Wisconsin River and broadened Lake Wausau. This park provides many amenities, plenty of parking, a boat launch, shoreline trails, shelters, grills, benches and picnic t...
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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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  • Madison, Wisconsin

    Kayak Lake Monona

    I like to put in at the Camp Randall Rowing Club Brittingham Boat House located at 617 N Shore Dr, Madison, WI 53703.  There’s a dock and free 3 hour parking.  Once in the water just paddle straight towards John Nolen Drive and go under the bridge and you’ll be in Lake Monona. Keep going and soak...
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  • Wausau, Wisconsin

    Kayak Lake Wausau

    5.0
    Kayaking on Lake Wausau lends to many adventures with bird watching at the Rookery as one of the most rewarding. On the south end of old Snake Bridge, now called McCleary on 17th Avenue, a small landing on Mallard Lane provides a less crowded location to drop your kayaks and easily park. Here you...
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