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

  • Fish Creek, Wisconsin

    Climb Eagle Tower in Peninsula State Park

    2.5
    From Highway 42 in Door County, WI, there are two entrances into Peninsula State Park, on the south and north ends of the park. If coming from the south, turn left onto Shore Road and take this road around the perimeter of the park until reaching the parking lot at the base of Eagle Tower. If tra...
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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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  • Baraboo, Wisconsin

    Bouldering at Devil's Lake State Park in Wisconsin

    4.5
    Devil's Lake State Park in Wisconsin offers some of the craziest views in the midwest as well as an abundance of supreme bouldering sites. To start off this endeavor there is one key item: a parking sticker. You can obtain one of these by heading over to either the north shore or south shore park...
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  • La Pointe, Wisconsin

    Hike Bay View Trail, Big Bay State Park

    2.6 mi
    Starting at the parking lot, you will walk into an open field with a couple picnic tables. On the right side of the field, the trail enters into a forest and walks along Lake Superior. There are several spots along the trail that you can find to cliff jump and go for a swim. The lake is so clear ...
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  • Grantsburg, Wisconsin

    Explore Crex Meadows

    5.0
    The Crex Meadows Wildlife Area is part of Wisconsin’s scenic Indianhead Country - located just north of Grantsburg. It’s 30,000 acres make it one of the largest wildlife areas in the state. Over 270 species of birds, 86 butterflies, and 720 different plant species call Crex Meadows home. Various ...
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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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  • South Range, Wisconsin

    Explore Wisconsin Point

    5.0
    If you’re in the Twin Ports area, (Duluth, MN and Superior, WI) be sure to check out Wisconsin Point. This peninsula is about 3 miles long and has several great spots to relax on the sandy beach (or swim in the chilly waters of Lake Superior). At the end of the peninsula is the Wisconsin Point Li...
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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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  • La Pointe, Wisconsin

    Hike the Point Trail at Big Bay State Park

    1.7 mi
    Located at the tip of Wisconsin on Madeline Island, Big Bay State Park is a must see for any Wisconsinite. To get to Madeline Island, you'll need to purchase a round trip ferry ride in Bayfield. The ferry is a quick 20 minute trip across Lake Superior. Once you get onto Madeline Island, head out ...
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  • Amberg, Wisconsin

    Explore Dave's Falls

    4.5
    0.25 mi
    Located in Amberg, Dave's Falls is in the heart of Marinette County, known for its various rapids, rivers, and waterfalls. The hike to the falls is well marked and very simple, and uses stairs for easier access. Hikers can shoot right for the falls, or continue left for a foot bridge and another ...
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  • Fish Creek, Wisconsin

    Fish Creek's Sunset Beach Park

    5.0
    From downtown Fish Creek in Door County, WI, head west on Main St. until the road dead ends at the water. Park your car on either side of the street and take a seat at a bench, explore the shoreline, or relax on the stone fence lining the shore. There's no better spot to catch the sunset in Fish ...
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  • Cross Plains, Wisconsin

    Hike through Indian Lake Park

    4.0
    4.7 mi / 324 ft gain
    442 acre park just outside of Madison is a perfect spot to escape for awhile. About a 20 minute drive from Madison makes it easily accessible even on a tight schedule. It provides a great place for lots of outdoor activities, year round.I love this place enough that I have been there many times a...
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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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  • 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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  • Baraboo, Wisconsin

    Camp at Devils Lake State Park

    3.7
    Devil's Lake State Park has 29 miles of trail that vary in difficulty. The most popular trails are the East and West Bluff trails that circle Devil's Lake and offer some of the best views in the park. If you want a more relaxing day, head to the beach! It's a family-friendly spot that is the perf...
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  • Sturgeon Bay, Wisconsin

    Hike along the shore of Whitefish Dunes State Park

    2 mi / 20 ft gain
    This specific trail is the shoreline from Whitefish Dunes to Cave Point County Park. This trail will take you approximately 30-60 minutes roundtrip depending on how much you explore or want to view the sights!  From the parking lot, walk forward toward the beach and turn toward the left (going No...
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