Outbound Collective logo

Wisconsin

Looking for the best cycling 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 Cycling Spots in and near Wisconsin

  • Waukesha, Wisconsin

    Bike or Run the Glacial Drumlin Trail (Waukesha to Wales Segment)

    5.0
    14 mi
    Your journey begins at the Fox River Sanctuary and E.B. Shurts Environmental Education Center at 810 College Avenue in Waukesha, Wisconsin. Parking is plentiful, and you'll find restrooms and bubblers (or, water fountains to you non-natives) available seasonally. The Glacial Drumlin Trailhead is ...
    Read more
  • Superior, Wisconsin

    Bike the Osaugie Trail

    4.0
    Biking along Superior Bay, you can experience the beautiful foliage during all of northern Minnesota and Wisconsin's seasons. It's the perfect way to get the Twin Ports experience: harbor views, train tracks, forests of birch trees, glimpses of Lake Superior and beyond.This bike trail is primaril...
    Read more
  • Elm Grove, Wisconsin

    Hike the Elm Grove Park Loop

    1 mi / 100 ft gain
    Elm Grove Park is one of the most picture perfect parks in the SE WI area, so be sure to stay for sunset as the sky lights up! The 1 mile long trail wraps the perimeter of the park. It is paved the entire way, if you want to venture off trail feel free. Dogs are permitted at this park! There is a...
    Read more
  • Brookfield, Wisconsin

    Hike or Bike the Lake Loop at Fox Brook Park

    1 mi / 0 ft gain
    You will find plenty of unique things going on at this park at all times. People swimming at the beach on the east end of the lake, people canoeing from the boat launch, grilling, hiking around the perimeter of the lake, and plenty of people fishing on one of two piers. Dogs are welcome and encou...
    Read more
  • 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...
    Read more
  • Fish Creek, Wisconsin

    Bike through Peninsula State Park

    5.0
    9 mi
    Situated between Fish Creek and Ephraim is Peninsula State Park, which is home to eight miles of Green Bay shoreline. Acres of northern hardwood forests, wetlands, meadows and 150-foot high dolostone cliffs showcase the beauty and magnificence of Wisconsin's Door County. BYOB (Bring Your Own Bike...
    Read more
  • 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 ...
    Read more
  • 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...
    Read more
  • McFarland, Wisconsin

    Bike the Lower Yahara River Trail at McDaniel Park

    2.5 mi
    This lakeside park has a newer bike/walking path. The park itself is an excellent spot for a picnic or catching a sunset! There is a nice play area and a rocky beach.   The path is known as the Lower Yahara River Trail and opened in 2017. It provides a non-road connection between Madison and McFa...
    Read more
  • Siren, Wisconsin

    Hike the Gandy Dancer Trail

    5.0
    While visiting the charming Northwoods town of Siren, I detoured for a hike on the Gandy Dancer Trail segment.   This trail was constructed to connect townships using old railroad beds.   Even the name honors the rhythmic, synchronized efforts of the workers in their rail nailing dance.   In tota...
    Read more
  • Rib Mountain, Wisconsin

    Stroll the Trillium Trail

    1.6 mi
    From South Mountain Road, turn onto Trillium Lane behind the Rib Mountain Fire Station. Follow Trillium Lane southeast, which acts as the bike path, to the dead-end where a small parking lot is. My friend and I strolled the wide paved path through the wooded wetland area. This project was just co...
    Read more
  • Stevens Point, Wisconsin

    Bike the Green Circle

    27 mi
    The Green Circle was established over thirty years ago, providing urban community members a trail system that encircles the entire Stevens Point area.  The 27 mile loop is comprised of 12 unique sections and is accessible at numerous locations. The official trail head is located at the Schmeekle ...
    Read more