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 53 trails covering 749 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 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 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 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 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...
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...
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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 Kiwanis Bike Trail, named for the Kiwanis Club that spearheaded the effort to build the trail, parallels the western bank of the Rock River through the southern Wisconsin community of Janesville....
The 53-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 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 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...
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 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 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,...
This path runs along the north side of Highway 11 and south of the city of Janesville. The eastern end starts about 3/4 of a mile west of I-39 and runs all the way to S County Road D, crossing over...
The Beerline Trail, so named because the corridor was once used by freight trains transporting the ingredients for beer to some of Milwaukee’s famous breweries, has contributed to the revitalization...
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,...
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 Root River Pathway uses a combination of off-road trail and on-road route to form a crescent around the City of Racine. The trail closely follows the bends of the Root River, making it a great...
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 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 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,...
Although short, the West Allis Cross Town Connector represents an important start to a future link between three trails in Milwaukee County. Currently, the trail begins at a junction with the New...
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 Glacial River Trail provides bikers, pedestrians, and in-line skaters with a 55.8-mile off-road/on-road rural route winding through farmland, prairie, wetlands, and woodlands as it passes through...
The Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for more than 120 miles in and around the city of Milwaukee on a changing terrain of flat...
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 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 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 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...
Moraine Hills State Park Trail offers a wonderful experience for any geology or nature aficionado. A moraine is an accumulation of earth and stones carried and finally deposited by a glacier....
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...
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 Beerline Trail, so named because the corridor was once used by freight trains transporting the ingredients for beer to some of Milwaukee’s famous breweries, has contributed to the revitalization...
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...
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,...
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 53-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 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...
About an hour northwest of Chicago, the beautiful Grant Woods Forest Preserve spans more than 1,000 acres, offering an outdoor respite of prairie, woodlands and marshes. The crushed limestone pathway...
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...
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 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...
Moraine Hills State Park Trail offers a wonderful experience for any geology or nature aficionado. A moraine is an accumulation of earth and stones carried and finally deposited by a glacier....
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 WE Energies Trail, so named because it uses a Wisconsin Energy Corporation utility corridor for much of its route, links Racine and Oak Creek in Racine and Milwaukee counties. Despite the presence...
The Glacial River Trail provides bikers, pedestrians, and in-line skaters with a 55.8-mile off-road/on-road rural route winding through farmland, prairie, wetlands, and woodlands as it passes through...
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 53-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 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 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 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 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...
Stretching from Afton to Janesville, the northern section of the Peace Trail offers a paved, tree-shaded route paralleling the Rock River and an active rail line. At its northern end, the trail merges...
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...
Although short, the West Allis Cross Town Connector represents an important start to a future link between three trails in Milwaukee County. Currently, the trail begins at a junction with the New...
The Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for more than 120 miles in and around the city of Milwaukee on a changing terrain of flat...
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 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...
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...
I returned on one of those great Midwestern fall days to complete the portion of the Glacial River Trail south of Jefferson. I found the few miles that were in-fact a former railroad. The rest of the trail is in the WI-26 freeway corridor or on rural roads and city streets, but the trail is all paved.
The city of Fort Atkinson is very attractive with trail amenities including public art. I again found that the TrailLink map was a necessity as the signage on the tail is sparse.
My only negative is there is no need to do the on-highway portion south of N Wright Rd unless you want to continue to the connection to the Spring Brook Trail that will take you into Janesville.
For an out and back trip consider places where you can use the parallel old WI-26 for a different landscape view.
Plenty of space to park stock trailer in gravel lot on Lake Shore Rd Clinton. Cute little covered bridge in small park with picnic tables was the start of my mule ride. There were trash receptacles, handicap accessible restroom & a wood post hitching rail. Many "sponsored" rest spots with wooden benches, picnic tables & some had roofs along the flat trail. Trail bed is wide, flat & firm as small crushed gravel & grass base. Views of plant/tree farm & rural properties after brief bit of SE side of Clinton. Mileage markers. Several blacktop road crossings. Easy, well-groomed trail. Small gravel lot at east end with trail map on kiosk. For lunch at Boar's Nest Bar ride Hill St (right uphill), stay right on Clinton St, quick Left along west side of the Park 1 block to stop sign Cty X. Ride directly across Cty X then straight across grass to cable picket line.
I-43 runs parallel to trail. Loud traffic but distance kept equines from becoming unnerved 🙂 Met a jogger, a hiker with a leashed dog on trail & 2 bicyclists at covered bridge. All were respectful of equines.
The Glacial River Trail in the Rock River valley is untypical for Wisconsin state trails in that it is entirely paved and not a rail-to-trail. It has a great mix of segments in the WI-26 freeway corridor, city streets and rural roads, with some good grades. I did the north part of the trail from Jefferson to the junction with the Wild Goose State Trail. There are no services provided by the trail owner, but the trail is free to use. The signage for the trail-turns is minimal so the Trail-Link map downloaded on your smart phone is a must. I especially enjoyed my ride thru the river towns of Jefferson, Johnson Creek and Watertown, where I took the time to ride around the downtowns. I will come back someday to do the south portion.
Parked at Cottage Grove today and biked out 23 miles and then back to car. It was annoying that we both paid our 5 dollars and then visited the rest room. No toilet paper in mens or women's and both stalls in women's were smeared with feces. Nice surface on trail. Not enough benches. This trail would definitely not qualify as a national rail trail.
I grabbed the trail north of Janesville on my road bike. Crossed the bridge over the highway and did about a mile on the county road before winding through a new housing development and finding the actual trail. It's in great shape, lots of gentle rolling hills and a couple of roundabouts but not a single person anywhere along the trail. I rode to Milton and most of the trail parallels the highway so it's loud on one side but beautiful and agricultural on the other side. I saw hawks and finches and no humans of any kind. It was pretty sweet. I only gave it 4 stars because of the highway driving . Otherwise it's a 5-star paved trail.
I have become fond of this trail for its natural surface and rural feel. Don’t try it with skinny tires since the ground can be soft in spots. Also great fun to encounter the occasional horses.
August 7th. Almost a perfect summer day and definitely perfect for a ride. Did a 30 mile round tripper from just south of Wisconsin line to south of McHenry and back. Condition of trail for that portion was about the best I've ever seen on any trail. Highly recommend parking at the trailhead for the Hebron Trail off Keystone Road at the north end of the trail. Hebron Trail will then take you straight east to hook up with Prairie Trail where you can begin and head south. No problems, well maintained all the way. Passes through several small, medium sized towns on this stretch with McHenry being the biggest. Plenty of access to services, food, water if you need it. Plan is to continue from McHenry on down south for my next leg of this trail. Can't wait to see what's ahead.
I like the canopied forest intermingled with open prairie. I live fairly close to the trail and have frequently ridden the trail from as far south as the city of Des Plaines to as far north as Libertyville. The trail extends farther south and north. For the parts that I ride the trail is mainly dirt, crushed gravel, and paved trails. During heavy rains, it will be washed out in many spots. Even during relatively dry periods, there is standing in several spots on the trail. Heading north from Des Plaines you have to cross railroad tracks. This is the private property of the railroad and they have done many things to dissuade riders from crossing the track. Farther north you have to cross Milwaukee Ave. without a light. Later you have to cross Dundee without a convenient light. You could use any bike on this part of the trail, and I have encountered a few adventurous riders on touring bikes despite some less than ideal conditions for thin tires. Overall it is a spectacular ride, especially when the prairie flowers are blooming.
One of the best bike trails in northern Illinois. Haven’t finished all the trails and look forward to being there again with it’s maintained quiet paths, and very few people using the trails as compared to the Des Plaines river bike path. Love the one way bike paths given the hills, our age and safety concerns. Given the steep hills and the effort it takes to reach the top each hill, I can understand why there are few people on the trails.
I rode the entire Long Prairie Trail today, round trip, from its east trailhead just east of Capron, over to the west trailhead at Roland Olsen FP. The ride is roughly 30 miles round trip. At both ends of the path there's a parking lot with a bathroom, picnic tables and maps.
The path itself is totally enjoyable. Except for a small section of path near the end of the east trailhead, the trail is in great shape. It transitions from blacktop to limestone, both of which are in good condition. Along the way there are plenty of benches, bathrooms and small towns where some amenities can be found. Most of the trail has a tree-covered canopy which was nice on a day like I had with total sunshine. There are some smaller stretches where you do get full sun exposure. The trail has an ample amount of signs warning riders about farm entrances, changes to the trail composition, informative signs and directions. I only saw 5-10 bikers on my route and maybe a few walkers/joggers. For the most part I think you can count on some peace and quite out here! Once I arrived at Roland Olsen FP I realized that the trail continued east. This isn't part of the Long Prairie Trail but as the map indicated, it goes up into Roscoe then turns north and goes all the way to Rockton Rd not far from the WI border. I suspect this is a nice section of trail.
A few pieces of advice while riding this trail, especially if you'll be riding the entire stretch. Wear glasses. Lots of bugs out here and they'll kill your eyes if they aren't covered. If it's sunny you'll want to put sunscreen on. Even though the majority of the path has tree cover, the sun still gets through. Apply bug spray in 'bug season'. You probably only need to do this if you plan on stopping frequently. Bring a couple of waters. Aside from a gas station in Capron and a small restaurant in Polar Grove, food and drinks are tough to find. Enjoy!
Mel & I drove from Raleigh to Milwaukee to see the Braves play the Brewers for a Mon-Wed series. We brought the Tandem bike. On Mon-Tues we rode out 6.2 miles from the west trail end-point to the Three Bridges Park and back. For convenience, We parked @ the Target parking lot. Along this section, The trail is mostly flat, well-paved, and very clean. It passes behind some industrial complexes, the State Fair complex, and some residential subdivisions. The street crossings requiring more care, were few, as the major street intersections utilized trail overpasses! As baseball fans, we felt honored to ride the HANK AARON TRAIL! If I come back with my single trail bike, I would love to ride the entire trail, and also the Oak Leaf Trail which joins up right where we began our ride!
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