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 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 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 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...
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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 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 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 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 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...
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...
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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 17-mile route traversing woodlands abundant with wildlife through several communities on the southern outskirts of Chicago. The trail travels from Brownwell Woods...
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 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...
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,...
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...
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 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 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 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...
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 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....
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,...
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 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...
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...
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 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 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 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 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 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 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 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...
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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,...
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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 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 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 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 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 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,...
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 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 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...
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...
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...
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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 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 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 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...
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 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 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 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...
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 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...
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 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....
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...
This trail can be described with one word...WOW!!! As construction nears completion (mostly landscaping) and pedestrian traffic moves onto the pedestrian path there is little to criticize. Awesome views of downtown Chicago and all the amenities of the lakefront make this trail a must do if you're in Chicago! I have only rode from Promontory Point to North Avenue Beach but look forward to riding the trail completely in the near future. Access to Grant Park, Millenium Park, Buckingham Fountain, Chicago River Walk, Northerly Island, Soldier Field, Museum of Science and Industry, Field Museum, Shedd Aquarium, Adler Planetarium, and Navy Pier plus numerous beaches along the route. Peak days and times will make the trail busy but there is much to enjoy all around you as you make your way through the hustle and bustle of Chicago and it's magnificent lake front views!
I rode the trail December 15, 2018 and it was very difficult!! Lots of very loose rock, shrubs across trail, etc.
I have run all along the St. Joseph River in the South Bend area when visiting . I was pleasantly surprised to find out that this section (riverside trail) was already plowed by 7 am on a Sunday morning (1/13/19) from the previous night’s snowfall. Thank you very much to whichever agency is responsible! You made me so happy!
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 have walked this frequently and have had a lot of fun and excitement saw many deer and small animals chipmunks, squirrels and saw a couple of cardinals, I walk this once a day and have a good time met a lot of nice people while walking .
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.
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