Find the top rated walking trails in South Milwaukee, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.
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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 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...
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 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 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,...
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 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 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 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 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 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 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...
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 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 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...
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An excellent example of land use in greater Chicago, the entire Skokie Valley Trail corridor is a rail-with-trail, paralleled by double tracks that sit about 40 feet to the west of the trail surface....
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...
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 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...
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...
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...
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 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 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 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 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 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 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 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 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 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...
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 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,...
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...
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 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...
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 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 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...
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....
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 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 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 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 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 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...
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 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,...
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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...
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Racine’s southeastern neighborhoods are home to the North Shore Trail, which extends south to the Racine–Kenosha county line. Because Racine County standardized its signs several years ago, you won't...
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...
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 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 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...
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...
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...
Really nice trail to walk or ride bikes. Good place to take your dog for long walks. Many access points. Even has an access point to Miller Park for bikers or trail hikers. Just wish they had a few trash receptacles every mile or so. Maybe then more people would pick up after their pooches.
I started at the southern end in River Forest. The trail was a flooded mudpit despite the fact that it hasn't rained in ages, was covered in huge fallen tree branches, and just in overall disrepair. Then, just past Fullerton, the trail literally disappeared INTO the Des Plaines River, leaving you NO choice but to turn back around. You're literally no better off on this trail than you would be if you just started off randomly making your way through the forest.
I have been riding this trail for 10 years now and it is awesome. I ride a MTB and a drop bar gravel bike and both are well suited for any conditions on this trail. I personally love to ride thru mud and water...it's just plain fun as is this trail.
This paved trail is a short (3 mile) north-south connector between two more prominent east-west rail trails -- the Lake Country Trail and the Glacial Drumlin State Trail. The route in its entirety parallels Cushing Park Road, running for more than a mile along the western edge of Lapham Peak State Park and Evans Prairie, where views of prairie grasses and wildflowers can be enjoyed by passing bikers and hikers. Elevation changes over the gently rolling terrain are easy to negotiate.
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.
I use the southern most part of Trail from Bloomindale Ave up to Ohare mostly. Trail is great, views, water at groves is close, only negative is all dead wood after flooding. I t can sit and block trails for months until its removed.
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.
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.
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