Sheboygan, Wisconsin

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

Top Chillin Spots in and near Sheboygan

  • Sheboygan, Wisconsin

    Hike through the Dunes at Kohler-Andrae SP

    4.5
    4 mi
    This park is known for its sand dunes, which rise above the blue waters of Lake Michigan. In addition to the well-known dunes, the park features many forested areas with towering pines that makes for absolutely beautiful and fantastical scenery. There are 7 trails ranging from 0.25 miles up to 2....
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  • Belgium, Wisconsin

    Hike the Quarry Lake Trail at Harrington Beach State Park

    1 mi / 15 ft gain
    This state park is about a 30 minute drive north from Milwaukee on I-43. It has beach access along it's entire length, multiple hiking trails, and a great quarry lake that can be used for fishing, hiking, or general exploring. From the parking lot, go south toward the signs for Quarry lake. There...
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  • Belgium, Wisconsin

    Hike the North and South Beach Trail at Harrington Beach State Park

    2 mi / 10 ft gain
    This state park is about a 30 minute drive north from Milwaukee on I-43. It has beach access along it's entire length, multiple hiking trails, and a great quarry lake that can be used for fishing, hiking, or general exploring. From the parking lot, you can go and hike one two areas (of course the...
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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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  • 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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  • 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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  • 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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  • 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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  • 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

    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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  • 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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  • Horicon, Wisconsin

    Hike through the Wetlands of the Horicon Marsh

    4.5
    5.25 mi
    Horicon Marsh is located about an hour north of Milwaukee. The wildlife refuge features several trails ranging from a quarter mile up to nearly 3 miles long. Terrain can vary slightly, but most of the land, especially around the wetlands, is flat. The marsh features an abundance of wildlife. Hund...
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