Explore the best rated trails in Waukesha, WI. Whether you're looking for an easy walking trail or a bike trail like the Eisenbahn State Trail and New Berlin Recreation Trail. With more than 55 trails covering 758 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
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The Bull Valley Road Shared-Use Path travels along the south side of Bull Valley Road in the city of McHenry, Illinois. The paved path is suitable for non-motorized uses including walking, jogging,...
The Eisenbahn State Trail gives a nod to Wisconsin’s German heritage in its name—Eisenbahn is German for “railway.” The strict translation, “iron road,” refers to the iron rails originally used as...
The Muskego Recreation Trail follows a corridor originally used by the Milwaukee Electric Railway & Light, an interurban railroad in southeastern Wisconsin. The corridor was later acquired by...
The Cushing Park Road Recreational Trail begins on the western outskirts of Delafield, a small community about 30 miles west of Milwaukee. From Delafield's Main Street, the trail heads south,...
Meadowbrook Trail parallels Meadowbrook Road offering a useful and convenient off-road route through northwest Waukesha. It begins at a connection to Lake Country Recreation Trail, a 15-mile east-west...
The Racine-Sturtevant Trail runs for 3.5 miles from the western side of Racine to near the eastern edge of the Village of Sturtevant. The trail occupies an abandoned rail corridor for most of its...
The 13.5-mile Lake Michigan Pathway keeps you in close touch with the sixth-largest freshwater lake in the world as it links rail-trails north and south of the port city of Racine. Along the way, the...
The White River State Trail is composed of two separate segments: a 12-mile stretch that runs between Elkhorn and just west of Burlington in Walworth County, and a 7-mile section that connects the...
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The Lake to Lake Bike Trail takes you through the beautiful terrain of the Kettle Moraine State Forest. It is a newer, well-maintained trail, with a wide, crushed limestone roadbed. It is used daily...
The Des Plaines River Trail runs alongside the Des Plaines River for just over 56 miles, protecting watershed habitat and forestland through much of Lake and Cook Counties. The trail is a natural...
The Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for more than 125 miles in and around the city of Milwaukee on a changing terrain of flat...
The paved New Berlin Recreation Trail runs straight as an east–west compass bearing for 7 miles through the western Milwaukee suburbs, from New Berlin to Waukesha. While it is void of trestles,...
Helping to extend the excellent network of trails around the city of Racine deeper west into the heart of the county, the Racine County Bike Trail serves as a disconnected addition to the...
The Sheboygan Interurban Trail follows the route of an electric railway that once ran between Milwaukee and Sheboygan from the early 1900s to 1951. The trail begins at Pebble Beach Road on the Ozaukee...
The Lake Country Recreation Trail runs from the western edge of Waukesha to Oconomowoc in Wisconsin’s Lake Country area. Most of the trail was built on a former Milwaukee-Watertown Interurban Railway...
Kinnickinnic River Trail (called the KK River Trail by locals) runs just over 2 miles in southern Milwaukee, following the river through a densely populated and industrial corridor. The trail links...
The Kenosha County Bike Trail is open in two sections separated by dense neighborhoods in the City of Kenosha. The northern segment runs northeast from 35th Street in the city to 1st Street at the...
The Prairie Crossing Bike Path is a hard surface trail connecting Mundelein to Grayslake in central Lake County, Illinois. The trail is perpendicular to the 30-plus-mile Millennium Trail, which it...
If you’re going to visit the historical communities that lie just west of Lake Michigan, why not use the former route of the venerable interurban railroad? The Ozaukee Interurban Trail stretches the...
The Stone Mill Trail runs between Lawrence Road in Harvard and Maxon Road in Chemung. The 1.5-mile, paved trail mostly parallels County Highway 17 (Ramer Road) and active railroad tracks, and will...
Broad blue skies strung with white cloud wisps; gem-green fields harboring cattails and butterflies; canopied glens giving way to cavernous quarries. It's all part of the ride on the Bugline...
The Lake Geneva Bike Path runs through the scenic resort city, offering connections to many of the community’s amenities. The trail has five unique, color-coded segments. The Blue Route is the...
The paved New Berlin Recreation Trail runs straight as an east–west compass bearing for 7 miles through the western Milwaukee suburbs, from New Berlin to Waukesha. While it is void of trestles,...
In 1957, baseball legend Hank “The Hammer” Aaron led the Milwaukee Braves to the first of two consecutive World Series appearances and a championship over the usually dominant New York Yankees. In...
The Seven Waters Bike Trail is a scenic corridor stretching more than 17 miles northsouth between Burlington and Muskego Lake into Waukesha County. The trail was originally three trails, locally...
The City of Franklin Hike and Bike Trail follows a corridor originally used by the Milwaukee Electric Railway & Light, an interurban railroad in southeastern Wisconsin. The corridor was later acquired...
If you’re going to visit the historical communities that lie just west of Lake Michigan, why not use the former route of the venerable interurban railroad? The Ozaukee Interurban Trail stretches the...
Racine County's eastern edge is home to the MRK Trail, a rail-with-trail that extends north from the City of Racine to the Village of Caledonia. Because Racine County standardized its signs several...
The KR Trail is a new addition to Kenosha County’s growing bike-ped network. The trail picks up where the Kenosha County Bike Trail leaves off, in Petrifying Springs Park. From the northwest corner of...
The Sheboygan Interurban Trail follows the route of an electric railway that once ran between Milwaukee and Sheboygan from the early 1900s to 1951. The trail begins at Pebble Beach Road on the Ozaukee...
The Millennium Trail currently spans just over 30 miles in two disconnected segments, but there are plans to extend it to 35 miles and connect it to the Des Plaines River Trail. The trail goes through...
The Milwaukee RiverWalk provides a pleasant way to get around Milwaukee from the Historic Third Ward, through downtown, and north to the Lower East Side. It also has easy connections to three other...
The Brown Deer Recreational Trail runs through the Village of Brown Deer, a suburb of Milwaukee. The tree-line route parallels an active rail line through commercial and residential areas. Mid-way,...
The Hebron Trail rolls across the northern Illinois prairie through the former corridor of the Kenosha and Rockford Railroad, known as the Kenosha Division Line at the time of its demise in 1939....
The Prairie Crossing Bike Path is a hard surface trail connecting Mundelein to Grayslake in central Lake County, Illinois. The trail is perpendicular to the 30-plus-mile Millennium Trail, which it...
The Racine-Sturtevant Trail runs for 3.5 miles from the western side of Racine to near the eastern edge of the Village of Sturtevant. The trail occupies an abandoned rail corridor for most of its...
The Rock River Parkway Trail in Janesville runs between Rockport Park and S. Jackson Street bridge on the north side of the river. Here, at the trail's eastern terminus, you can easily link to Spring...
The Long Prairie Trail journeys across the width of agricultural Boone County for nearly 14 miles on the railroad corridor previously used by the Kenosha and Rockford Railroad, later known as the...
Janesville's Spring Brook Trail provides an important non-motorized route to many of the city's popular recreational amenities. The pathway begins just off the eastern terminus of the Rock River...
The 13.5-mile Lake Michigan Pathway keeps you in close touch with the sixth-largest freshwater lake in the world as it links rail-trails north and south of the port city of Racine. Along the way, the...
The Kenosha County Bike Trail is open in two sections separated by dense neighborhoods in the City of Kenosha. The northern segment runs northeast from 35th Street in the city to 1st Street at the...
Meadowbrook Trail parallels Meadowbrook Road offering a useful and convenient off-road route through northwest Waukesha. It begins at a connection to Lake Country Recreation Trail, a 15-mile east-west...
The Long Prairie Trail journeys across the width of agricultural Boone County for nearly 14 miles on the railroad corridor previously used by the Kenosha and Rockford Railroad, later known as the...
The Lake Country Recreation Trail runs from the western edge of Waukesha to Oconomowoc in Wisconsin’s Lake Country area. Most of the trail was built on a former Milwaukee-Watertown Interurban Railway...
The Pike River Pathway is a paved, multi-use trail that runs along both sides of the reconstructed Pike River through the Village of Mount Pleasant and unincorporated parts of Racine County. The path...
The Duck Lake Nature Area Trail follows the southern side of Lake Como between Lake Geneva and Como, Wisconsin, not far from the Illinois state line. The trail is more rustic than most rail-trails and...
Broad blue skies strung with white cloud wisps; gem-green fields harboring cattails and butterflies; canopied glens giving way to cavernous quarries. It's all part of the ride on the Bugline...
The Wild Goose State Trail is a premier rail-trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. If you are looking for a peaceful and beautiful place to visit, this trail has it...
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The Fox River Trail runs diagonally along its namesake waterway through Waukesha in southeastern Wisconsin (just outside of Milwaukee). A trailhead at the E.B. Shurts Environmental Education Center in...
The Chain O' Lakes Bike Path is a paved trail that runs between E. Grand Avenue in Fox Lake and Grant Woods Forest Preserve to the east. The trail parallels the railroad track and Rollins Road/CR 31,...
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The Prairie Trail runs the length of McHenry County and is managed by the McHenry County Conservation District. The rail-trail spans just over 26 miles from the Wisconsin border and the farms and...
The Eisenbahn State Trail gives a nod to Wisconsin’s German heritage in its name—Eisenbahn is German for “railway.” The strict translation, “iron road,” refers to the iron rails originally used as...
The City of Franklin Hike and Bike Trail follows a corridor originally used by the Milwaukee Electric Railway & Light, an interurban railroad in southeastern Wisconsin. The corridor was later acquired...
The 52-mile Glacial Drumlin State Trail between Cottage Grove and Waukesha provides a glimpse into the past when glaciers bore down on southeastern Wisconsin in the last Ice Age. Those gigantic sheets...
The Sheboygan Interurban Trail follows the route of an electric railway that once ran between Milwaukee and Sheboygan from the early 1900s to 1951. The trail begins at Pebble Beach Road on the Ozaukee...
The Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for more than 125 miles in and around the city of Milwaukee on a changing terrain of flat...
The Cushing Park Road Recreational Trail begins on the western outskirts of Delafield, a small community about 30 miles west of Milwaukee. From Delafield's Main Street, the trail heads south,...
The Robert McClory Bike Path runs the length of Lake County, knitting together a string of communities on the north shore of Chicago all the way to the Wisconsin border. In 1997, the trail was named...
Helping to forge a connection between the northern and southern segments of the Kenosha County Bike Trail, the Kenosha Pike Bike Trail also has plenty to offer in its own right, giving trail users a...
The Lake Geneva Bike Path runs through the scenic resort city, offering connections to many of the community’s amenities. The trail has five unique, color-coded segments. The Blue Route is the...
Left from Long Lake. Perfect for what I was looking for. Varied scenery, lots of gorgeous meadows, some forest, then swamp-like lands as you get closer to Mauthe Lake. Milder hills compared to what you’d find road biking in the area. Some shade (we left around 10:30am) but depending on time of day and position of sun you could have more shade. I didn’t need bug spray but recommend bringing just incase. Trail wasn’t busy at all. Very enjoyable ride.
We rode from Belgium to Oostburg. I didn't realize that the Sheboygan Interurban was all paved. Even though I read the trail description I was still expecting gravel when we crossed Hwy. K. The trail seems well maintained and is in good condition. This section of the trail from Hwy K to Oostburg is mostly rural and follows a railroad track. A really beautiful ride. It has a suburban feel when you go through Cedar Grove. There is one road you have to take through an industrial section of Cedar Grove. On the north side of Cedar Grove at Hwy 32 & Commerce St. is a nice trail head with tables and shade and that also has a clean porta-pottie.
When you reach Oostburg the dedicated trail ends and you ride the streets. The first road north through Oostburg is a quiet residential street and it takes you to the trail head at the Oostburg train depot. There are really clean bathrooms inside and tables too. No tables outside but across the tracks to the west is Kups Coffee and Ice Cream. This is where we turned to head back to Belgium.
Flat, paved and tree covered, what could be better. A few places pavement was in need of repair but very passable. From Capron about a half mile the tree covering was not as heavy but it was cloudy at the time so not a problem. We started on the Stonebridge trailhead which was crushed gravel and transitioned smoothly to the Long Prairie trail. Just a wonderful ride. Restaurants in Capron did not open till ten or eleven but there was a Casey’s gas station.
Very beautiful quick ride. Mauthe lake was flooded so it started out a very feet soaking ride... but it makes an experience!
I rode this trail in its entirety a few days ago. The portion through West Bend is paved, but the remainder is crushed limestone. A few portions of the trail have some plant growth, but it did not interfere with my ride. Only one small area on the gravel portion felt loose; the remainder of the trail was fine. I would recommend to plan your trip with needed supplies (sunblock, hydration, food, cell phone, and bike repair gear) as some portions of the trail are quite isolated for many miles. Overall, I did enjoy my ride and will likely be back!
Lived in Kenosha for 3 years and would go on this trail weekly. It's incredible on the lake
Started from Kohler-Andrae SP. Not a fan of on road biking, but nice quiet roads. Nice little coffee ice cream shop “Kups” in Oostburg. Next door at the Oostburg red building are public restrooms. Paved bike trail from Oostburg south.
3 short loops each abt 3 to 4 miles long. Short rolling hills. Adulta will be fine, children in training wheels or bike without gears moght be a challenge. Dam area have canoe rental.
Here a great R2T for those in SE Wisconsin! The Bugline Trail, just NW of Milwaukee. Oddly named, but a sweet trail. I started in Merton, rode to Menomonee Falls and back. 26 miles round trip, all paved. A great mix of woods, open areas, and some developed areas. There are several little towns along the trail (Merton, Sussex, Lannon, Menomonee Falls) where you can pick up snacks if needed.
As it passes thru Lannon, WI -- which provided the limestone that built much of Milwaukee -- you will see lots of quarry lakes, including one that is just shockingly blue!
If you are in the area, give it a try!
Awesome trail. I took my fat tire bike for a 40 mile bike ride. This is great for dogs too since there's the des plaines river. Plenty of shade
Went last weekend and enjoyed it. Tons of hills. One time I had to walk the bike up the hill. Other times had to drop 4-5 gears very quickly to get up the hill. Definitely want to go back in the fall.Beautiful view by the damn.
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