Explore the best rated trails in Chesterton, IN. Whether you're looking for an easy walking trail or a bike trail like the Illinois & Michigan Canal State Trail and North Judson Erie Trail. With more than 60 trails covering 649 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 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...
The Vale Park West Pathway is a multiuse trail in the Chicago suburb of Valparaiso. At 0.7 mile long, the trail passes through a mix of woodland and prairie, as well as over a creek on a 220-foot...
Note: Erosion caused by surging waves off Lake Michigan has caused the trail to collapse in sections. The eastern half of the trail along Lake Michigan is closed indefinitely. See the Chicago Park...
The Pennsy Greenway stretches between Calumet City, Illinois, and Schererville, Indiana. The trail begins at the southern end of the Burnham Greenway on the eastern edge of the Forest Preserve...
The Palos Heights Bike Trail offers a north-south route through residential and commercial areas on the west side of the community. It's also a key connector between two regionally important...
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 Cal-Sag Trail (or, Calumet-Sag Trail) is currently under active construction. It currently has a competed section of over 15 miles, stretching from near its western terminus at the John Husar I&M...
The Burnham Greenway is composed of two distinct portions that both run along a former railroad corridor between Chicago and Lansing, Illinois. There are plans to extend and connect these short...
When complete, the LaSalle Trail will travel an arrow-straight 3.5 miles between Roseland Town Park in Roseland and the Indiana–Michigan state line. Michigan is currently working on building a trail...
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...
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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....
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...
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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,...
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...
Although just shy of three miles, the Veterans Memorial Trail provides a wooded, paved trail experience for residents in the Chicago suburbs of Romeoville, Lemont, and Woodridge. Those seeking a...
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...
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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When complete, the Veterans Memorial Trail will stretch close to 12 miles, connecting a series of memorials honoring US veterans from every era. At present, 1.3 miles are complete and usable, located...
Leave the cars at home: the Route 30 Bike Path gives users an alternative way to travel from the Village of Frankfort in the east, through Mokena to New Lenox in the west, a distance of over 7.5...
The Thorn Creek Trail offers a paved route traversing woodlands abundant with wildlife through several communities on the southern outskirts of Chicago. The trail travels from Brownwell Woods in...
When complete, the LaSalle Trail will travel an arrow-straight 3.5 miles between Roseland Town Park in Roseland and the Indiana–Michigan state line. Michigan is currently working on building a trail...
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...
The Iron Horse Heritage Trail in Portage, Indiana, runs for over 2 miles between Max Mochal Road (SR 149) at the east end and Hamstrom Rd. at the west end. The trail passes through a greenway corridor...
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...
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...
Note: Erosion caused by surging waves off Lake Michigan has caused the trail to collapse in sections. The eastern half of the trail along Lake Michigan is closed indefinitely. See the Chicago Park...
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 Branch Trail follows the North Branch of the Chicago River over 20 miles through Cook County. The trail was originally a dirt path often used for horseback riding; though it’s now paved, an...
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...
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....
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 Orland Park Bikeway provides a great connector across the Chicago suburb of Orland Park. On its southern end, the trail begins at W. 159th Street and winds its way through Centennial Park, which...
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...
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Illinois’ Centennial Trail runs through parts of three suburban counties from Willow Springs Road to Romeo Road/135th Street southwest of Chicago. The trail occupies a thin strip of land between the...
The Thorn Creek Trail offers a paved route traversing woodlands abundant with wildlife through several communities on the southern outskirts of Chicago. The trail travels from Brownwell Woods in...
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 Illinois and Michigan Canal State Trail follows the eponymous waterway alongside the Illinois River. It traverses the I&M Canal National Heritage Corridor, designated in 1984 and the first...
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 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 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,...
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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...
The 9-mile Green Bay Trail runs parallel to Chicago's Metra commuter rail line north of the Chicago city limits. Stretching through North Shore towns such as Kenilworth, Winnetka, Highland Park and...
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,...
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...
The Preservation Path is a two-mile paved trail in the community of Matteson, Illinois. The path begins on Vollmer Road and terminates at the Old Plank Road Trail. The trail is paved with center...
The Palos Heights Bike Trail offers a north-south route through residential and commercial areas on the west side of the community. It's also a key connector between two regionally important...
Running between the suburbs of Chicago Heights and Joliet, the Old Plank Road Trail offers views of oak trees and sugar maples, prairie grasses, and wildflowers that peek up through the...
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...
Leave the cars at home: the Route 30 Bike Path gives users an alternative way to travel from the Village of Frankfort in the east, through Mokena to New Lenox in the west, a distance of over 7.5...
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 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 Pennsy Greenway stretches between Calumet City, Illinois, and Schererville, Indiana. The trail begins at the southern end of the Burnham Greenway on the eastern edge of the Forest Preserve...
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...
Note: Erosion caused by surging waves off Lake Michigan has caused the trail to collapse in sections. The eastern half of the trail along Lake Michigan is closed indefinitely. See the Chicago Park...
When complete, the LaSalle Trail will travel an arrow-straight 3.5 miles between Roseland Town Park in Roseland and the Indiana–Michigan state line. Michigan is currently working on building a trail...
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...
The Dunes Kankakee Trail is a 5.5-mile walking and bike path that It exists in 2 discrete segments: one that is 2.4 miles paralleling County Road 25 East, and the other segment east of that that is...
Although just shy of three miles, the Veterans Memorial Trail provides a wooded, paved trail experience for residents in the Chicago suburbs of Romeoville, Lemont, and Woodridge. Those seeking a...
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....
I agree with the reviews of the trail south of Lake Cook Rd. It’s ok for a few miles south but there’s a notable difference of trail conditions from the trail north. Two different counties and budgets to maintain them, I assume. Traveled this trail multiple times this past COVID season. It’s my first year biking in 40 yrs and wow, what a great trail.
Runs along the river. The park is nice but the trail seems a little dirty with trash around the sides. There are multiple benches along the trail for resting. Not a bad trail, but not a very pretty trail either. So if you’re looking for some sight-seeing as you run then this may not be the ideal spot to run.
This trail is the beat I’ve ridden on. I’m new to biking but this trail, so far, is my favorite. Paved the entire way or off roading choice if you’d like as well. I like to mix it up a bit.
We rode this trail in early Nov 2020, and liked it so much we returned two weeks later for another run. This is one of the most interesting of the suburban trails we have ridden, with a number of bridge crossings of the creek. The trail winds through various Forest Preserve forests and meadows on its north end, before veering due south at Glenwood for a long straight stretch, then wanders through several pleasant neighborhood-adjacent parks before ending at Sauk Lake.
Well worth adding the very peaceful and scenic Black Trail loop around Sauk Lake, just be prepared for that one steep hill at the back, lol! An added benefit is that Thorn Creek Trail is amazingly smooth, with very few of those root-bump cracks that you always seem to feel so much more on the return trip.
Ignore the nonsense in the "Parking and Trail Access" section about the northern trailhead being at "Wapum" (Actually Wampum) Lake Woods. There's no trailhead there, they need to change that. Park at Lansing Woods on 186th just east of Torrence.
I am thrilled to share that the worst part of this trail mentioned in several reviews here has been freshly repaved as of November 2020 (from Route 30 all the way north to Colfax Street). Previously, this section was marred by huge cracks that ran across the full width of the trail every 20 yards or so. These cracks were between 1 and 2 inches wide – enough for foliage to blossom within – and were absolutely jarring to hit on a road bike. Now, this section is buttery smooth and an absolute pleasure to ride on.
This now places the worst section of this trail in Hammond north of Interstate 80/94. With the exception of the new pedestrian flyovers that cross Columbia and Calumet Avenues, the rest of Hammond's share is quite rough. Still, I enjoy completing the entirety of the trail from Downtown Hammond to Crown Point and back. When I start off in Hammond, I typically park in the visitor's lot of the Hammond Police Department off Douglas St. for some extra peace of mind with respect to my vehicle being left unattended for hours (downtown Hammond doesn't have the rosiest of reputations).
I parked just north of Golf at 294 right over the train tracks. Took the trail north and I loved it. The tracks do separate the trail and I’m surprised it’s not connected. The people who make and maintain these trails are national heroes. The dirt road north is perfect for mountain bikes. I rode about 7 miles to highway 68 I think it is. Awesome.
Agree with all the posters below: this is a great trail and another example of what gems these FPD trails are! So close to urban, highway, and residential, yet a secluded ride in the woods.
If riding south and west, park at the Red trailhead at Lansing Woods, just east of Torrance on 183rd Street. Late season and winter, mind the wind direction before choosing which way to ride this trail, as much of it runs due south.
11.8 miles to the end of the red trail, then you can tack on 4 miles on the black loop. 11.0 miles to the east end of the Old Plank Road trail.
Flat tide on a cement trail. Benches online the trail. Not much shade so in the summer months it may be a hot ride, A few roads that you need to cross.
Best work out I had in a long time, I have been going for a moth + I love the u hills and the terrain is perfect.
Very nice. Paved trail , pretty color change, nice scenery along the river . Very rider friendly.
This is a great trail for kids. My son and I went rollerblading. The trail is flat, so no big hills to manage. We had an awesome time!
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