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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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 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 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 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 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...
As its name implies, the beautiful Prairie Duneland Trail offers snapshots of the flora and fauna—from hardwood forest to remnant prairie grasslands—that once dominated this region. In spite of the...
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...
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,...
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 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...
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 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...
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...
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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 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...
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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 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 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 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,...
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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 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 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 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...
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,...
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 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 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 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...
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 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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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 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 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...
As its name implies, the beautiful Prairie Duneland Trail offers snapshots of the flora and fauna—from hardwood forest to remnant prairie grasslands—that once dominated this region. In spite of 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....
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...
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 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 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 Illinois & Michigan Canal provided the final link in the water route from the east coast to the Gulf of Mexico by connecting Lake Michigan to the Mississippi River via the Illinois River. Today,...
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...
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,...
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 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,...
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 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 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 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 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 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 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 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 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....
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 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 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,...
As its name implies, the beautiful Prairie Duneland Trail offers snapshots of the flora and fauna—from hardwood forest to remnant prairie grasslands—that once dominated this region. In spite of 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...
My wife and I found this trail for the first time today. It was a beautiful, scenic 20+mile stretch which was immaculate and well kept. The asphalt had zero cracks and looked brand new. Bridges over the Tippecanoe River and Indian creek were very nice. Got to meet some of the volunteers - Friends of the Panhandle Pathway. Very Nice people!. Drove 2 hours from Dyer Indiana to get there. It was definitely worth the drive.
What a mess, needs some gravel, no signs pointing to where to go.
Last fall, the FPD extended this trail to Forest Glen Park, near the Metra stop and across from the Chicago Canine Rescue. It is a wonderful addition and saves me the trouble of taking 1.5 miles of city streets to the trailhead at Devon & Caldwell. Others have covered this trail extensively. I just wanted to add that the total distance from Devon & Caldwell to the southern gate of the Chicago Botanic Gardens is just over 17 miles (not 20 miles as it says on Google maps and the FPD map). The 20 miles includes the entire circuit around Skokie Lagoon. You obviously wouldn't be riding around the entire Skokie Lagoon circuit in order to get to the Chicago Botanic Gardens. Once inside the southern gate, it is approximately 1 mile to the main building at the Gardens. All together, it is about 19.5 miles from Forest Glen to the main building at the Gardens.
The Lincolnwood connection to the Sauganash Trail mentioned in another review is now in place. The trail is now around 5 miles long, but has busy road crossings at Devon, Touhy, Lincoln and Howard. Also the photos on this page are of the Lake County section of the SV Trail. It will still be awhile before the two are connected.
The directions to the difficult to find Southern trailhead is go to 600 W off of Hwy 24 and go North. 600 W is 4.5 miles West of the Hwy 29 exit on to Hwy 24/35. Once on 600 W go 0.25 miles to 50 N at the Pisgah Christian Church and go East another 0.25 miles to the trailhead. The trail starts 0.8 miles South of this trailhead at a dead end. From the dead end the trail heads North around 22 miles to another dead end at 11th Street in Winnemac. There are trees along the trail for about quarter of the way and it follows Hwy 35. The trail is flat and paved asphalt. The trail is very picturesque
as it travels through the small towns between Logansport and Winnemac. If you are looking for a getaway from Indianapolis, it is about an hours drive to Logansport. You won't be disappointed.
Just spent an hour trying to find parking to get on trail in Lombard. Street parking limited to 1 hour and public parking limited to Lombard residents. Very frustrating. Web site should have been more helpful as should trailheads
Essentially, worse than an unpaved road as we biked thru standing water with tadpoles swimming about.
My friend and I love doing the I&M canal as it is mostly shade and flat. The path is crushed stone and covered with trees. The path comes close to the river once in a while, but don't come to this path expecting a nice river view. This is a remote path with few rural towns in between. I recommend the part between Morris and Channahon as this part seems to be kept up regularly. Also check for path closures on the I&M before you go. We have had to re-plan our trip a few times finding out the part we wanted to go on was closed. Currently west of Seneca is not kept up with over run grass on the path and around it, we just found that out.
My husband, son and myself rode this trail May 24, 2017. We started at the Lake Avenue, Wilmette trailhead. We quickly ran out of both path and trail signs when we got to Cumnor Road at the end of a section traversing Townley Field in Winnetka. We used Google Maps on our phone to find the trail again by turning left on Cumnor, right on Melrose, left on Abbotsford, left on Ivy Lane, and looked for the trail on our right. North of there we had no troubles following the trail.
We passed several playgrounds and parks, some rustic areas and others which had been re-planted with native flora, as well as easy access to several North Shore downtown areas.
When we reached the crossing at Lake-Cook Rd we turned left (west) and rode past the Turnbull Woods and McDonald Woods Forest Preserves to reach the Chicago Botanic Gardens. Entrance is free and the Gardens are extensive. There is a charming cafe at which we refreshed and relaxed before returning to our starting point in Wilmette.
This is a trail to which you can return again and again, and take many fun side trips.
I've only ridden this trail once, near Channahon (which has great parking at the State Park), and it was very good and interesting. Not paved, but still easy to bike or walk. In the area in which I rode, you have the I and M Canal on one side and the Des Plaines River on the other. As you ride, you go past historical sites of the canal which are a great bonus. Also, you can fish in the DuPage River at Channahon.
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