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 Illinois Prairie Path (IPP) is one of the country's first rail-trail conversions. It consists of five connected trail segments with three main branches that converge at Volunteer Park in Wheaton....
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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 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...
Indiana's Panhandle Pathway links Winamac to Kenneth and communities in between, 21 miles of paved cycling, skating and walking. This spectacular rail-trail passes through bucolic Midwestern farmland,...
Located east of Lakeshore Drive, the Chicago Lakefront Trail is an 18.5-mile linear park along Lake Michigan that includes beaches, volleyball courts, playgrounds, baseball diamonds, tennis courts and...
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 Oak Savannah Trail takes its name from the unique ecosystem that it runs through. Once pervasive throughout northern Indiana, the oak savannah is a transitional zone between forest and prairie,...
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 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...
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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 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...
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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...
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 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 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...
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....
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The Bloomingdale Trail, part of “The 606” park system, is a 2.7-mile, elevated rail-trail on Chicago’s northwest side. Built on a former rail line, the trail sits nearly 20 feet above four of 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 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...
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 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...
Traveling along the Wauponsee Glacial Trail, you'll be surprised just how quickly you can move from an urban environment into the rolling fields of the Midwest. Starting in Joliet, within shouting...
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...
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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 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 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 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 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 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 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,...
The beautiful North Branch Trail is named for the North Branch of the Chicago River, along which it winds. At its northern end, the trail begins at the south end of the Chicago Botanic Garden and...
The 20-mile Old Plank Road Trail travels over the original Michigan Central Rail Road (MCRR) line, a railroad started about 1850 that ran from Lake Station in East Gary to Joliet. The rail was...
The Des Plaines River Trail and Greenway traverses north–south along the route of its namesake river along its course through both Lake and Cook counties. The corridor protects 85% of the riverine...
The Bloomingdale Trail, part of “The 606” park system, is a 2.7-mile, elevated rail-trail on Chicago’s northwest side. Built on a former rail line, the trail sits nearly 20 feet above four of the...
The Cal-Sag Trail (or, Calumet-Sag Trail) is currently under active construction. As of August 2015, it has a competed section of about 10 miles, stretching from near its eventual western terminus to...
The Iron Horse Heritage Trail in Portage, Indiana, runs for 5 miles between Max Mochal Road (SR 149) at the east end and County Line Road near US 20 at the west end. The trail passes through a...
The Erie Lackawanna (EL) Trail represents the longest contiguous trail in Northwest Indiana, running 17-miles from Crown Point north to Hammond. This trail passes through wetlands and open space on an...
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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 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 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...
The Erie Lackawanna (EL) Trail represents the longest contiguous trail in Northwest Indiana, running 17-miles from Crown Point north to Hammond. This trail passes through wetlands and open space on an...
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...
Located east of Lakeshore Drive, the Chicago Lakefront Trail is an 18.5-mile linear park along Lake Michigan that includes beaches, volleyball courts, playgrounds, baseball diamonds, tennis courts and...
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 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 Cal-Sag Trail (or, Calumet-Sag Trail) is currently under active construction. As of August 2015, it has a competed section of about 10 miles, stretching from near its eventual western terminus to...
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 Bloomingdale Trail, part of “The 606” park system, is a 2.7-mile, elevated rail-trail on Chicago’s northwest side. Built on a former rail line, the trail sits nearly 20 feet above four of the...
The Pennsy Greenway is currently open in three segments between Calumet City, Illinois, and Schererville, Indiana. The northern portion begins at the southern end of the Burnham Greenway in Calumet...
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 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 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 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,...
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...
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 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 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...
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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 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...
Great trail! Accessible, scenic and well-kept. I've lived walking distance from the trail for 20 years. It can be perfect walking, jogging and biking. We've enjoyed it for family outings with the kids when they were children. For safety, solo activities are best avoided as the trails can be isolated and very wooded in some areas. avoided for worecommend group outing
I rode most of the trail below Joliet on July 28 , 2017. Except for the closures shown on the DNR website (downtown Morris, Marseilles to Ottawa, and two bridges out near Utica), the trail was in decent condition. (I was glad I was on a hybrid and not a skinny bike.)
Joliet to Morris was in good shape. Some of this section is dull, some parts are pleasant.
The closure in Morris has been there for years, and the street detour is easy and not too long.
Morris to Seneca is my new favorite section: quieter and more woodsy than the rest. No trail problems.
Seneca to Marseilles was fine. There’s a good view of the Illinois River if you go a few blocks south of the trail in downtown Marseilles.
Marseilles to Ottawa was mostly dull and pointless. I went around the barricade just west of Marseilles and had to carry my bike over downed trees, which I expected. It got old after a while, though, and since the trail was boring at that point, I wish I hadn’t bothered. There’s a nice paved road next to the trail – use that instead.
Ottawa to Utica is in decent shape, except for the bridge that’s out, and I like this section. I went about 9 miles west from the Fox River aqueduct in Ottawa and came to the bridge. I was tempted to take my shoes and socks off and wade through the two inch deep stream and continue, but turned around instead. (It’s only another mile or so to downtown Utica).
I like the section below Utica, but with the bridge out, I didn’t feel like continuing.
If you accept the closures and the dull parts, the I&M is a good Illinois trail.
Just the right distance now that it connects with the the trail in
Lincolnwood. It connects to Emily Oaks Nature Center (more trails), and has several water fountains. Very nice urban trail.
Southern 3 mile extension opening Saturday, August 12, at Foster and Kostner aves. Irene C. Hernandez Picnic Grove, LaBaugh Woods, Chicago.
Being a Chicagoan I had yet to ride the 606 until last week. My first impression was what a great trail. The idea of traveling without motor traffic and no stops for almost three miles flies by. The ride on the return trip was much slower as there was more traffic on The 606. Still it was the fastest way to travel through this area. The 606 has also improved an area that at one time the term less desirable would of been an understatement. The area has improved and the beauty of The 606 matches the surrounding homes and neighborhoods. This in my opinion is from The 606. We found all the people very pleasant on our journey and they seemed to be very proud of The 606. we saw the Chicago Police Department in a strong presence on our Saturday journey. The CPD was on both foot and bicycle. My only complaint is that it is too short of a trail. Hopefully Chicago will develop more of these useful neighborhood enhancing trails. It is all good on The 606.
Even before this trail connected with Wicker Park, I rode this trail often each summer, sometimes going to Griffith, sometimes about a mile short of the end, sometimes all the way to Griffith. I love this trail. I rode it for the first time in several years on 7Aug 2017, and hasn't changed much, except for a couple detours. And as a RR fan, love that it crosses Griffith Junction and with all the old cabooses, cars, etc.
I love this trail. Lots of shades, beautiful scenery, lots of animals like birds squirrels bunny's deer... Bears.... ;-) (just kidding about the bears). So.. yeah its an awesome trail. I will keep coming back here.
The 606 ultra-smooth surface is great for inline skating!
Very nice 10 mile trail with direct connection to 2.5 mile spur to Iron Horse Heritage Trail. Travels through woods with a few road crossings and suburban scenes. About 6 miles of the trail was newly paved and very high quality. The rest was somewhat bumpy as others have noted but nothing that was too distracting or dangerous. I spent two weekend mornings here (30 miles and 40 miles) traveling from Michigan City by car (~25 mins) to easily accessible parking lot in Chesterton.
I often take this trail when I want to get places, not just as a way to spend some time outdoors. The trail connects directly with the West Branch Dupage River Trail, which then if you take north ~6 miles connects to the Illinois Prairie Path, which then connects you to basically everything. Additionally, the path goes through three of the best forest preserves in the region -- Springbrook Prairie, Greene Valley, and Waterfall Glen.
The section along 75th St east of Plainfield/Naperville Rd is somewhat narrow and not used a lot, but is made of crushed gravel and has a nice connection at Washington St via an underpass to the West Branch Dupage River Trail.
rode sw from Brandon Road lock. do not ride this trail on a road bike with anything less than 700x28. I flatted on one of the sections of loose gravel. The ride itself is pleasant enough in that area...lots of tree cover...but the canal itself is overgrown, and not what I expected as far as scenery goes
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