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 61 trails covering 4393 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 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...
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...
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...
First-time visitors to the Oak Savannah Trail might be surprised at the profusion of natural areas they’ll encounter as they travel the 9.5 miles between Hobart and Griffith in northern Indiana’s...
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...
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...
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 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 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 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 Chesapeake and Ohio Greenway (also referred to as the C&O Trail) offers a short, paved route through Merrillville, a town just a few miles south of Gary and the southern tip of Lake Michigan. The...
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...
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 Erie Lackawanna Trail connects Crown Point and Hammond, two former rail junctions whose early fortunes were tied to the tracks carrying people and goods to and from Chicago. Despite traveling...
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...
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...
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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....
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...
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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...
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 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...
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 Marquette Trail, also known as the Marquette Greenway, will one day span more than 50 miles through Northwest Indiana, connecting communities along the southern shore of Lake Michigan. The...
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 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. The paved pathway...
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 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...
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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 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 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...
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...
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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...
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...
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...
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The Tinley Creek Trail is currently in two segments. This southern segment is within the South Green Belt Forest Preserve between Flossmor and Matteson, just west of I-57. The trail traverses wooded...
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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...
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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,...
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 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...
The Techny Trail links downtown Glenview, a charming village northwest of Chicago, with the Techny Basin, a scenic wetlands area adjacent to the West Fork of the Chicago River's North Branch....
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...
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 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 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 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 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...
First-time visitors to the Oak Savannah Trail might be surprised at the profusion of natural areas they’ll encounter as they travel the 9.5 miles between Hobart and Griffith in northern Indiana’s...
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 trail system in Waterfall Glen Forest Preserve makes a loop around the entire park. The preserve is geologically significant, featuring glacier-carved rock ridges, ravines and wetland potholes,...
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 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...
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 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 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 community of Granger is tucked into the north end of Indiana, bordering Michigan. The community itself, through the Friends of Granger Paths recognized the need for safe, separate areas for...
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 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 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...
This trail is very poorly marked. It was very difficult to find the trail when crossing streets and such. Also no signs pointing which way to go when the trail intersected with another path. Also to much of the trail is along busy streets! It’s also very short. also
I love it because i saw everything and see cool boats and it was not dirty it's so clean and beautiful i have fun and it was awesome
Porter County should really consider paving this trail as it would be a great asset to attracting bikers to the lake shore
I hope that this trail will improved soon. It would be a great safe connector from the state park to Michigan city, but currently, it is not a great option
Very intense ride for my first time riding there so relaxing great parking and the smell of nature is in invigorating¿¿¿
Rode Greenway Trail for the 1st time, southbound from Addison. Essential to constantly pay attention to where you’re going. Had to stop to use detailed trail map a few times/TrailLink app. No sign telling you to exit Illinois Prairie Path in Elmhurst. No direction given at end of Rex Avenue: go left thru residential or right to enter Sleepy Hollow Park? Went left but no trail signs. Went back, entered park behind a guard rail where you’ll ride on a wood chips trail. At Butterfield, didn’t see direction on where to pick up the trail on the other side. (thru the parking lot behind an office building to the S.E. corner). TrailLink app is a must with occasional stops to check it. Not all that enjoyable for me. Rated Fair. Henry entered park behind a guard rail,Where are you encounter a wood chips trail. At Butterfield,
The hills were so steep that you'd have to brake several times going downhill just to prepare for the quick turn up ahead. We had to do this atleast once per mile, and it was stressful. However, I did enjoy the workout the hills provided, but you need to be in good shape to do them otherwise you made need to walk the bike uphill a few times like my dad did. You also have to cross two busy highway roads. It is partially shady; we went on a hot sunny day thinking it would be shady the whole time but it was not so be sure to wear sunscreen. Now for the positives, good workout if you are in shape, beautiful scenery with lots of changing outlooks like marshes to prairies, plenty of benches to stop at, and of course the waterfall. Overall, I am glad we went. But being 40 minutes away means we probably won't be returning, atleast not for the biking. Would cautiously recommend it.
It’s always nice to be able to go in a loop rather than a straight line and back. This is a really nice trail with a lot of variety of scenery and good curves. There are places where it’s really noisy because of the proximity to major highways and there are a few busy intersections to cross. The trail is in good shape but is getting close to needing repair. Overall this is a great trail and I would give it a 4 of 5.
This is a lovely, lively bike trail. Have tried it few times on Saturday mornings, and really enjoyed the morning sun and the fresh air. Beautiful city view. Must try trail.
Wish you could see more of the river as you ride, but nice, smooth trail, not very crowded.
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