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Chesterton, Indiana

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

Top Hiking Spots in and near Chesterton

  • Dune Acres, Indiana

    Hike the Cowles Bog Trail, Indiana Dunes National Lakeshore

    3.0
    4.4 mi / 200 ft gain
    To get to the trailhead parking lot: take Mineral Springs Road towards the community of Dune Acres. Just before you get to the guard shack for the community, turn onto the gravel road to the right - there will be signs indicating Cowles Bog Trail parking. Once parked, walk back towards the Dune A...
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  • Porter, Indiana

    Indiana Dunes Trail 8 And 7 Loop

    1.95 mi / 370 ft gain
    Indiana Dunes Trail 8 and 7 Loop is a 2 mile loop hike that takes you past scenic views located near Chesterton, Indiana.
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  • Chesterton, Indiana

    Hike the 3 Dune Challenge

    5.0
    1.5 mi / 552 ft gain
    Start at the Indiana Dunes State Park Nature Center (the first exit off the roundabout in the park after the toll), after receiving your park map, and follow the 3 dune challenge. This challenge, looping trails 8 and 4, involves climbing to the top of Mt. Jackson (176 feet), Mt. Holden (184 feet)...
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  • Gary, Indiana

    Hike the Dune Succession Trail, Indiana Dunes National Lakeshore

    4.5
    1 mi / 150 ft gain
    This hike provides a great opportunity to explore the variable landscape and terrain in Indiana Dunes National Park. From the parking lot head north on a paved walkway toward Lake Michigan's shoreline. Next, walk down the boardwalk to the beach. Once you reach the coast, you'll have amazing view...
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  • New Carlisle, Indiana

    Hike the Glacier Flats Trail at Spicer Lake Nature Reserve

    5.0
    2 mi
    The Glacier Flats Trail is a 1.5 mile loop that guides you through the Old Field Trail and past the Buttonbrush Wetland and observation platform. You will continue along the trail past an open field and then into the woods.  Along the way you will enjoy the colors of the wildflowers and likely an...
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  • Chicago, Illinois

    Millennium Park Trail

    5.0
    0.63 mi / 26 ft gain
    Millennium Park Trail is a loop trail that takes you past scenic surroundings located near Chicago, Illinois.
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  • Palos Park, Illinois

    Hike the Cap Sauers and Swallow Cliff Loop

    3.0
    4.74 mi / 259 ft gain
    The Swallows Cliff Woods, an 800 acre preserve, is known for its 100 ft bluff that provides visitors with a steep stair workout. On top of the bluff, however, there are less strenuous trail options, leading through the hilly, forested terrain, past wetlands and streams.
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  • Willow Springs, Illinois

    Black Oak Trail

    4.5
    2.64 mi / 148 ft gain
    The trails traverse a rolling glacial highland of oak woods and prairie. The hiking trails connect to miles of multi-use trails where you can hike, mountain bike, cross country ski and snowshoe. Lastly, there is an interpretive center with exhibits about local nature and history. The trailhead...
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  • Willow Springs, Illinois

    Cemetery Hill

    2 mi / 100 ft gain
    Just outside of Chicago the Palos Region of the Cook County Forest Preserve offers a few thousand acres of dirt single track and limestone paths. Here you will find rolling hills and bluff that will rev up your hill workouts. This single track loop is great for mountain biking and trail running...
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  • Brookfield, Illinois

    Salt Creek Greenway Trail

    13.99 mi / 551 ft gain
    This trail is almost 7 miles one-way (14 miles out-and-back) of paved path, makes for an ideal biking (especially those of us with road bikes), skating, and even running path. The trail runs out-and-back along the Salt Creek in Brookfield, IL. The trailhead is right near the Brookfield Zoo (for a...
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  • Willow Springs, Illinois

    Saganashkee Slough

    5.0
    6.92 mi / 512 ft gain
    Saganashkee Slough is a loop trail that takes you by a lake located near Lemont, Illinois.
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  • Oak Brook, Illinois

    Run the Fullersburg Woods Loop

    4.7
    6 mi
    This is a six-mile loop along the banks of the Salt Creek in Oakbrook, IL. The flat trail features trees and wildflowers (great walk to do in autumn). Trail is also good for bike riders. There is a picnic area and the Graue Mill and Museum. Graue Mill is 150 years old and played a part in the Und...
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