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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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 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...
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 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 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 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 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 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,...
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...
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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 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...
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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 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...
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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 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....
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 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...
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 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 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 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...
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 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...
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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 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...
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...
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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 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...
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,...
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 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 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 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 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 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 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...
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 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...
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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...
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 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 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 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 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 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,...
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 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 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...
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,...
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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,...
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 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...
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 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 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 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...
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.
Decided to do this trail instead of the Old Plank Trail. Much better than the long straight trail. Many winding turns, the loop through the Preserve at the end is a nice turn around spot. Signage could be a little better though.
I thought the trail was great but there are many low hanging branches on the north side of the path that really need to be trimmed.
Road the trail today and had a great experience. If part of it was once bumpy, it has been repaired. Most of the trail is new and all of it is terrific to ride. Beautiful scenery, bathrooms along the way, easy to park and get on. We rode all 10 miles and will come back again and again.
We live near the southern section of this trail, so we have rode that portion multiple times. It is a night and day difference with the northern portion. The southern end is just not very pleasant. Trail is in poor shape, poor signage and due that section of river, the area is prone to flooding. Viaducts are usually impassable, flora is mostly invasive species, lot of trash , etc etc.
The north end however (maintained by Lake Co. as opposed to Cook Co.) is just great. Well groomed, tons of signage, usable viaducts, clean, etc. This section meanders through forest, open prairie , some farmland. The scenery is beautiful, especially mid summer with the plants in full bloom.
Highly recommend sticking to north of Cook Co. We plan on finishing the entire trail a section at a time until we hit Wisconsin!
I live in southwest Lake County, Indiana, so this trail is a little far for me, but well worth it. I've ridden it twice in two different sections, and it is an outstanding trail that cuts right through rural north central Indiana. It is completely paved, there are enough benches along its length as well, and, at least during the week, seems completely devoid of people. There are also a few small parking lots along the way. Check this trail out for sure.
Nice Trail It was alittle hard to find trailhead in Winamac drove right past it, but they were constructing what looked like a new one with facilities a block away.....be sure to update the directions Trail does run along side of hwy 35 Had a nice lunch at Jacks
Walked the trail from Bryn Mawr to Touhy and had a excellent time. very happy to see the Touhy overpass being built and the call boxes that can summon medical help if needed are excellent to have if a person does not have a cell phone to call 911 once my bicycle is repaired I will be riding this trail from Bryn Mawr to Dempster.
Great trail to walk on once my bicycle is repaired I will be riding this trail all the way up to Skokie , nice that Sauganash Park is by the trail for use of the drinking fountain or restrooms.
The reviews are ALL about biking. This trail is sort of inline friendly but it has a lot of flotsam, sticks, debris from trees, and there are lots of repairs made with that sticky tar substance, that the skate wheels are not too good on. Some parts are pretty rough asphalt and some are fairly smooth. Bigger wheels are probably better, though they also make you faster. The street crossings are semi cut curbs with lots of bumps and broken cement to make your wheels stick, unless you're good at navigating these obstacles or good at jumping. This gets worse the further east you go on the trail. *There's a few places where the trail runs downhill (going W at Wolf Rd for one) and then spills directly into a busy street. You'd better practice your stopping skills. I think they should send a sweeper down this path at least a few times a month. I bike this trail and it's really good for that. I've skated it as well, but that was over 10 years ago when I was more confident. One bad fall with a twisted rotator cuff made me more wary since (a jogger wouldn't make way and my avoidance of her made me lose it). People walking 3 abreast and those with dogs on long leashes are also good to avoid.
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