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 55 trails covering 628 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 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 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...
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 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...
The Marquette Trail offers picturesque views of Lake Michigan as it travels through the Indiana Dunes National Lakeshore. This scenic route follows an abandoned rail line through a variety of diverse...
The Cal-Sag Trail (or, Calumet-Sag Trail) is currently under active construction. As of early 2018, it has a competed section of about 13 miles, stretching from near its western terminus at the John...
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...
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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...
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 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...
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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...
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 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...
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 Indiana-Michigan River Valley Trail currently runs for more than 5 miles through Niles, Michigan, on the eastern bank of the St. Joseph River. The trail occupies a former New York Central Railroad...
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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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...
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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 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 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 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,...
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 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...
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 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 Marquette Trail offers picturesque views of Lake Michigan as it travels through the Indiana Dunes National Lakeshore. This scenic route follows an abandoned rail line through a variety of diverse...
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...
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...
The Cal-Sag Trail (or, Calumet-Sag Trail) is currently under active construction. As of early 2018, it has a competed section of about 13 miles, stretching from near its western terminus at the John...
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...
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 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 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 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 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...
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...
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...
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 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...
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 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 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...
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...
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 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...
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...
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...
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,...
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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...
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 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...
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...
Lake Renwick Preserve is home to an artificial lake of the same name that was created from former quarries where aggregates for concrete were once mined. Today, the lake is a recreational amenity 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 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...
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...
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 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 path between Bemis Woods in Western Springs to the Brookfield Zoo is great! Nicely paved and easy to ride. You have to cross a couple of busy streets, but most of them have traffic signals.
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 like this trail. Indiana is doing nice things for bikers/runners recently. You do have to stop at street crossings, but when you make it to the Whiting lakefront, it's worth it. Beautiful. It also passes a minor league baseball stadium and the mascot HOF.
I just wanted to update my review since the separation has (mostly) been completed. There are now 2 trails, one for biking and one for running. It definitely helps with the congestion. There are still some areas you need to pay attention to when the paths cross and you'll still come upon someone that is on the wrong path, but it's much better than it was.
I've ridden and run this trail several times. It's really nice, newly paved and smooth. Well taken care of and has nice views. The only warning is this trail can get pretty busy so be cautious on it.
I've rode nearly 90% of this trail and enjoyed 100% of it! Definitely not a paved trail as many have noted and a bit muddy in spots (West of Marseilles), you have to appreciate the awesome views this trail has to offer! Small towns spaced every 5-6 miles offer a rich historical past, shopping, dining, many parks, and a glimpse of life as it was back in the days. Plenty of nature to photograph so make sure you bring your camera. The trail can use some much needed maintenance in areas, while other spots offer a flat and firm surface. Recent trees that have fallen over the trail have been cut. At one section between Utica and Ottawa there is a bridge out, but a small wooden plank has been erected to navigate the small creek. Plan an all day ride and you will not be disappointed with the scenic views and fun this trail can offer!
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 bridge that crosses the DesPlaines River at the east end of the trail (along Willow Springs Road) has been replaced and is now open.
We rode the main trail and explored a few trails leading off the main trail on our mountain bikes. The only complaint is the lack of water. We are going back in a couple of days to do two loops and try more side trails. We will bring a cooler with our supplies
Loved exploring this trail today! A bit hillier than Prairie or Salt Creek but nice rolling up and down both ways. We easily found Sag Quaries with Google Maps off of 83 and jumped right on. Couldn't believe no street crossings all the way to Nicks BBQ at the end of the trail! We stopped for lunch than headed back. Nice 24 miles! Loved the Lake Katherine area and the low traffic on this trail! We'll do it again in the fall as the foliage will be beautiful!
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