Find the top rated trails in Chesterton, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
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The northern section of the Tinley Creek Trail is a series of color-coded connected loops and spurs that weave through several forest preserves in Cook County. The 24-mile trail system is paved,...
El Paseo runs through the vibrant Chicago neighborhood of Pilsen, once home to a large Czech population but now the center of the Lower West Side’s Latino community. The neighborhood is filled with...
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The Salt Creek Trail travels nearly 27 miles from the Brookfield Zoo to Busse Woods Forest Preserve. Along the way it connects several beautiful county forest preserves and other woodland...
The Dunes Kankakee Trail is a 3-mile walking and bike path that begins in the Indiana Dunes State Park and travels south to Chesterton. It connects the Calumet Trail, which is also in the state park,...
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The Skokie Valley Trail in Cook County parallels active train tracks in the Village of Skokie, providing easy access to both the Oakton–Skokie and Dempster–Skokie stations on the CTA’s Yellow Line....
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The Monon Trail in Lake County, Indiana—not to be confused with the trail of the same name in Indianapolis—links the two Chicago suburbs of Hammond and Munster. The paved trail occupies an abandoned...
As the name suggests, the Lake George trail travels along the north shore of Lake George, turning north at Calumet Ave/US 41 to skirt the east shore of Wolf Lake. From Lake George the trail also heads...
The Southern Dupage County Regional Trail connects multiple of the larger forest preserves in Dupage county together. Starting near the intersection of 75th st and Ogden Ave in Aurora, the trail runs...
The Hickory Creek Bikeway offers nearly 4 miles of paved pathway through a wooded preserve. On its western end, the trail begins at Hickory Creek Barrens Nature Preserve and Lincolnway Road; on the...
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The Bloomingdale Trail, part of “The 606” park system, is a 3-mile, elevated rail-trail on Chicago’s northwest side. Built on a former rail line, the trail sits 17 feet above four of the city’s...
The Northerly Island Trail offers access to a vast, natural oasis in one of the largest cities in America. Chicago’s Northerly Island—actually a 91-acre peninsula—was designed by Daniel H. Burnham,...
In just a few short miles, the Wauponsee Glacial Trail leaves the urban confines of Joliet to bask in open farmland and reclaimed tallgrass prairie where the bison roam again. Named for a glacial lake...
The North Branch Riverwalk is a 0.6 mile biking and walking trail located on Chicago's northside along the North Branch of the Chicago River, nestled between Gordon Tech High School and Lane Tech High...
The John Husar I&M Canal Trail is the northernmost trail developed on the Illinois & Michigan Canal National Heritage Corridor. The Illinois & Michigan Canal provided the final link in the water route...
The North Shore Channel Trail extends from the junction of Green Bay Road and McCormick Boulevard in northern Evanston to the junction of Lawrence Avenue and Francisco Avenue in Chicago. All but the...
Although less than 1 mile long, the West Bank Walkway offers lovely views of the St. Joseph River in downtown South Bend. Midway, a converted railroad trestle over the waterway connects trail-goers to...
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The northern portion of the East Bank Trail was one of the first rail-trails in Indiana, opening in 1988. The asphalt-surfaced trail stretches for about 0.5 mile through tree-lined South Bend...
The Old Plank Road Trail travels nearly 22 miles between Chicago Heights and Joliet across a densely populated suburban landscape, where you’re never far from a café or espresso stand. Still, you...
The Erie Lackawanna Trail rolls nearly 18 miles between Crown Point and Hammond, two former rail junctions whose early fortunes were tied to the tracks carrying people and goods to and from Chicago....
The Lincolnwood Valley Line Trail connects the existing Valley Line Trail (Sauganash Trail) to the Skokie Valley Trail in Cook County. Like the previous segments, this trail occupies a former Union...
The Chicago Lakefront Trail is aptly named; it spans 19 miles along the shore of Lake Michigan, going right through downtown Chicago and passing many cultural and tourist attractions throughout the...
The Major Taylor Trail is named after legendary African American cyclist Marshall “Major” Taylor, who was one of the most celebrated bicycle racers of the late nineteenth century, setting several...
The Lincolnwood Valley Line Trail connects the existing Valley Line Trail (Sauganash Trail) to the Skokie Valley Trail in Cook County. Like the previous segments, this trail occupies a former Union...
Turkey Creek Trail is a short but sweet walk or ride through the beautiful Ivan Gatlin Nature Preserve in the northwestern Indiana community of Schererville. This wetland area provides the opportunity...
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 Southern Dupage County Regional Trail connects multiple of the larger forest preserves in Dupage county together. Starting near the intersection of 75th st and Ogden Ave in Aurora, the trail runs...
South Bend’s Northside Trail closely follows the east bank of the St. Joseph River from Howard Park to the western edge of Mishawaka. Along the way, you’ll have access to Viewing Park and Veterans...
In just a few short miles, the Wauponsee Glacial Trail leaves the urban confines of Joliet to bask in open farmland and reclaimed tallgrass prairie where the bison roam again. Named for a glacial lake...
The North Shore Channel Trail extends from the junction of Green Bay Road and McCormick Boulevard in northern Evanston to the junction of Lawrence Avenue and Francisco Avenue in Chicago. All but the...
The Monterey Erie Trail occupies the same railbanked corridor as the longer North Judson Erie Trail to its west, and the two rail-trails are planned to be linked in the future. Monterey and North...
Indiana’s Panhandle Pathway follows a former Pennsylvania Railroad corridor out of Winamac south to Kenneth. Along the way, the trail links the communities of Star City, Thornhope, and Royal Center...
The North Judson Erie Trail occupies the railbanked right-of-way of the former JK Line Railroad, running 9 miles from downtown North Judson southeast to US 35 near Bass Lake. Eventually, the trail...
Little Calumet River Levee Trail stretches from Munster to Gary, Indiana. The trail zigs and zags through a number of local parks including Riverside Park, Wicker Memorial Park, Homestead Park,...
The Salt Creek Trail travels nearly 27 miles from the Brookfield Zoo to Busse Woods Forest Preserve. Along the way it connects several beautiful county forest preserves and other woodland...
Prairies and dunes are just two of the natural features you’ll experience on the Prairie Duneland Trail, located just a few miles south of the Lake Michigan shoreline and the Indiana Dunes National...
Just 1 mile long, the Valley Line Trail—also known as the Sauganash Trail—extends between Bryn Mawr Avenue and Devon Avenue in the Chicago neighborhood of Sauganash. Two bridges allow for safe...
The Thorn Creek Trail offers a paved 17-mile route traversing woodlands abundant with wildlife through several communities on the southern outskirts of Chicago. The trail travels from Brownwell Woods...
The Monon Trail in Lake County, Indiana—not to be confused with the trail of the same name in Indianapolis—links the two Chicago suburbs of Hammond and Munster. The paved trail occupies an abandoned...
The Calumet Trail traverses the south side of the Indiana Dunes National Lakeshore, a unique ecosystem of forest, marsh, dunes and beach along Lake Michigan. This dirt and crushed limestone path...
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The Riverside Trail winds along the west bank of the St. Joseph River for just over 3 miles in northern Indiana's South Bend. Several benches along the way allow you to take in the beautiful river...
The Illinois Prairie Path (IPP) was one of the nation’s first rail-trail conversions. It consists of five connected trail segments with three main branches that converge at Volunteer Park (West...
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The Veterans Memorial Bikeway begins in Hebron in northwestern Indiana’s Porter County. From there, it follows the diagonal route of the former Pennsylvania Railroad for just over 8 miles through Lake...
The Skokie Valley Trail in Cook County parallels active train tracks in the Village of Skokie, providing easy access to both the Oakton–Skokie and Dempster–Skokie stations on the CTA’s Yellow Line....
The Indiana-Michigan River Valley Trail currently runs for more than 2 miles through Niles, Michigan, on the eastern bank of the St. Joseph River. The trail occupies a former New York Central Railroad...
The Dunes Kankakee Trail is a 3-mile walking and bike path that begins in the Indiana Dunes State Park and travels south to Chesterton. It connects the Calumet Trail, which is also in the state park,...
The Major Taylor Trail is named after legendary African American cyclist Marshall “Major” Taylor, who was one of the most celebrated bicycle racers of the late nineteenth century, setting several...
Just 1 mile long, the Valley Line Trail—also known as the Sauganash Trail—extends between Bryn Mawr Avenue and Devon Avenue in the Chicago neighborhood of Sauganash. Two bridges allow for safe...
The Old Plank Road Trail travels nearly 22 miles between Chicago Heights and Joliet across a densely populated suburban landscape, where you’re never far from a café or espresso stand. Still, you...
The Union Pacific Recreation Path offers a short route through the Village of Lincolnwood's east side between Devon and Touhy avenues. Following the former Union Pacific Railroad, the rail-trail...
In just a few short miles, the Wauponsee Glacial Trail leaves the urban confines of Joliet to bask in open farmland and reclaimed tallgrass prairie where the bison roam again. Named for a glacial lake...
The North Judson Erie Trail occupies the railbanked right-of-way of the former JK Line Railroad, running 9 miles from downtown North Judson southeast to US 35 near Bass Lake. Eventually, the trail...
The Salt Creek Trail travels nearly 27 miles from the Brookfield Zoo to Busse Woods Forest Preserve. Along the way it connects several beautiful county forest preserves and other woodland...
Prairies and dunes are just two of the natural features you’ll experience on the Prairie Duneland Trail, located just a few miles south of the Lake Michigan shoreline and the Indiana Dunes National...
The Chicago Lakefront Trail is aptly named; it spans 19 miles along the shore of Lake Michigan, going right through downtown Chicago and passing many cultural and tourist attractions throughout the...
Little Calumet River Levee Trail stretches from Munster to Gary, Indiana. The trail zigs and zags through a number of local parks including Riverside Park, Wicker Memorial Park, Homestead Park,...
The northern portion of the East Bank Trail was one of the first rail-trails in Indiana, opening in 1988. The asphalt-surfaced trail stretches for about 0.5 mile through tree-lined South Bend...
The Riverside Trail winds along the west bank of the St. Joseph River for just over 3 miles in northern Indiana's South Bend. Several benches along the way allow you to take in the beautiful river...
The Thorn Creek Trail offers a paved 17-mile route traversing woodlands abundant with wildlife through several communities on the southern outskirts of Chicago. The trail travels from Brownwell Woods...
Indiana’s Panhandle Pathway follows a former Pennsylvania Railroad corridor out of Winamac south to Kenneth. Along the way, the trail links the communities of Star City, Thornhope, and Royal Center...
The Southern Dupage County Regional Trail connects multiple of the larger forest preserves in Dupage county together. Starting near the intersection of 75th st and Ogden Ave in Aurora, the trail runs...
This is an amazing trail in the city I love. It’ll take you north to Hollywood st and south to the south short cultural center. North you can continue on the streets until hooking up with more trails all the way to WI. South is the same all the way to Indiana. But... ...it’s currently under construction. They’re separating the bike path from the runner/walking path so the trail is being worked on now. When it’s finished it will be magnificent. Just wanted to give you a heads up!
Have photographed 30 deer since walking from Dam No 4 Woods to Campground Road Woods, a nice relaxing walk to see squirrels, chipmunks, birds, rabbits and o yes the deer. This is a beautiful trail to walk and much safer than walking on the street or road. I live one mile from Dam No 4 Woods so it is easy for me to get there.
I rode this trail to get my 100 mile ride in from Chicago. I liked it. The other reviews are true, it can be a little bumpy and there were a couple sections that could have been marked better but overall it was nice. There were places the trail seemed to split and I can’t wait to go back to explore where they go.
Remember the big flood? Tornadoes? This trail is maintained as well as possible considering our financial state in this state. The only real problem this year is the collapsed & under repair Morris viaduct that closed the trail. You must ride on the road to Stratton Park, then back on a continuous trail through Lockport. Safe from traffic, beautiful river views, professionally repaired washed out sections plus fairly responsive fallen tree removal keeps the trail ridable. Occasional trees down may require lifting bike over. I try to break off branches to clear a temp path till they cut it up usually withing a week or two.
Some shallow flooding occurs after heavy rains between Ottawa & Marseilles that is still ridable...Appox 2-4 in deep max.
All in all a wonderful fitness ride from Morris to Buffalo Rock.
The Crown Point section is now GREAT! Smooth new asphalt.
However, the Schererville section is horrendous! pouring a little tar into cracks for many years has not stopped the prolific and gaping cracks!! The Griffith and Highland sections also need repaving also, still a lot of cracks. The Schererville section needs REPAVING; it's the worst.
Maybe they need to stop the snowmobiles on the trail, the quad runners, and the service vehicles from driving on the pavement!
It used to be skateable for roller blades. Now we can't even stand to ride road bikes or a recumbent trike on the trail. Wrist and rear hurting cracks that jar your teeth they hit so hard.
The Cat3 wannabe's still ride on it as there are no bike lanes in Northwest IN to be out on the streets and the people in vehicles expect you to ONLY be on a trail.
Yes flat nature trail with no facilities unless you go into N Judson but not very helpful at the other end. There were low branches but for the most part clean. Only came across a hand full of people and they were part a youth group ride that were ahead of us. It was a very hot windy day, not the best conditions for cycling. We parked in town unable to find the parking lot with the picnic table which is on Rt 10 east of town pass over trail parking up on right
Nice scenic path covering 2 creeks and a small bridge. Connects to a longer path if wanting an extended ride. Definitely a few hills but nothing to taxing, especially with the tons of bench's they have directly next to the path you can take a break whenever you like. A bunch of shaded path makes it both beautiful and a great choice on a hotter day.
Started at Dam No 4 Woods and walked to Golf Rd and Big Bend Lake , saw plenty of animals deer, squirrels , chipmunks and beautiful scenery along the trail. Nice peaceful walk plenty to see , nice surface to walk on not muddy saw 1 deer by the 294 underpass and south of Oakton St saw 2 deer in the woods about 20 feet away from me, what a beautiful sight to see a doe and her fawn took pictures of this. It was a beautiful walk and I had a lot of fun.
Decided to do this trail instead of the Old Plank Trail. Much better than the long straight trail. Many winding turns, the loop through the Preserve at the end is a nice turn around spot. Signage could be a little better though.
I thought the trail was great but there are many low hanging branches on the north side of the path that really need to be trimmed.
Road the trail today and had a great experience. If part of it was once bumpy, it has been repaired. Most of the trail is new and all of it is terrific to ride. Beautiful scenery, bathrooms along the way, easy to park and get on. We rode all 10 miles and will come back again and again.
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