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Chesterton, IN Inline Skating Trails and Maps

1026 Reviews

Looking for the best Inline Skating trails around Chesterton?

Find the top rated inline skating trails in Chesterton, whether you're looking for an easy short inline skating trail or a long inline skating trail, you'll find what you're looking for. Click on a inline skating trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type
57 Results
Activities
Length
Surfaces
Type

Bloomingdale Trail (The 606)
2.7 mi
State: IL
Asphalt, Concrete

Cal-Sag Trail
16.2 mi
State: IL
Asphalt

Centennial Trail (IL)
13 mi
State: IL
Asphalt

Chicago Lakefront Trail
19 mi
State: IL
Asphalt, Concrete

Erie Lackawanna Trail
17.6 mi
State: IN
Asphalt

Erie Trail
11.1 mi
State: IN
Asphalt

Hickory Creek Bikeway
3.7 mi
State: IL
Asphalt

Illinois Prairie Path
58.52 mi
State: IL
Asphalt, Concrete, Crushed Stone

Indiana-Michigan River Valley Trail
17.5 mi
State: MI
Asphalt, Concrete

Iron Horse Heritage Trail
2.4 mi
State: IN
Asphalt

John Husar I&M Canal Trail
8.9 mi
State: IL
Asphalt

Lake George Trail
3.1 mi
State: IN
Asphalt

Major Taylor Trail
7.6 mi
State: IL
Asphalt

Monterey Erie Trail
0.6 mi
State: IN
Asphalt

North Branch Trail
25.5 mi
State: IL
Asphalt

North Shore Channel Trail
8.3 mi
State: IL
Asphalt, Concrete, Dirt

Northerly Island Trail
1 mi
State: IL
Asphalt, Concrete

Northside Trail
3 mi
State: IN
Concrete

Oak Savannah Trail
10.2 mi
State: IN
Asphalt

Old Plank Road Trail (IL)
21.6 mi
State: IL
Asphalt
Accordion

Panhandle Pathway
22.5 mi
State: IN
Asphalt

Pennsy Greenway
14.5 mi
State: IL, IN
Asphalt

Prairie Duneland Trail
10.3 mi
State: IN
Asphalt

Riverside Trail (IN)
3.4 mi
State: IN
Asphalt

Route 30 Bikeway

7.6 mi
State: IL
Asphalt

Salt Creek Trail (IL)
28.6 mi
State: IL
Asphalt, Cinder, Woodchips

Skokie Valley Trail (Cook County)
2 mi
State: IL
Asphalt

Thorn Creek Trail
17.2 mi
State: IL
Asphalt

Tinley Creek Trail (North)
24 mi
State: IL
Asphalt

Tinley Creek Trail (South)
3.6 mi
State: IL
Asphalt

Valley Line Trail
1.1 mi
State: IL
Asphalt

Veterans Memorial Trail (IL)
2.7 mi
State: IL
Asphalt

Veterans Memorial Trail (IN)
1.9 mi
State: IN
Asphalt

Burnham Greenway
5.3 mi
State: IL
Asphalt

Coal Line Trail
1.5 mi
State: IN
Concrete

Dunes Kankakee Trail
1.8 mi
State: IN
Asphalt

East Bank Trail
1.7 mi
State: IN
Asphalt, Concrete

Green Bay Trail
6.5 mi
State: IL
Asphalt, Concrete, Crushed Stone

LaSalle Trail
3.5 mi
State: IN
Asphalt

Little Calumet River Levee Trail

13 mi
State: IN
Asphalt

Mishawaka Riverwalk
2.6 mi
State: IN
Asphalt, Brick, Concrete

Monon Trail (Lake County)
4.4 mi
State: IN
Asphalt

Orland Park Bikeway
6.7 mi
State: IL
Asphalt, Boardwalk, Concrete, Gravel

Techny Trail
3 mi
State: IL
Asphalt, Concrete

Union Pacific Recreation Path
1.2 mi
State: IL
Asphalt

Wauponsee Glacial Trail
22.3 mi
State: IL
Asphalt, Crushed Stone

Chessie Trail
1.45 mi
State: IN
Asphalt, Concrete

El Paseo
0.1 mi
State: IL
Asphalt

Granger Paths
5 mi
State: IN
Concrete

Vale Park West Pathway
0.7 mi
State: IN
Concrete

Fairview Walking Trail
0.7 mi
State: IN
Asphalt

Lake Max Trail
1.63 mi
State: IN
Asphalt, Concrete

Lincoln Memorial Trail
1.8 mi
State: IN
Asphalt, Concrete

Palos Heights Bike Trail
2 mi
State: IL
Asphalt

Preservation Path
2.1 mi
State: IL
Asphalt

Turkey Creek Trail
0.8 mi
State: IN
Asphalt

West Bank Walkway
0.6 mi
State: IN
Concrete
Trail Image Trail Name States Length Surface Rating
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...
 IL 2.7 mi Asphalt, Concrete
The Cal-Sag Trail (also known as the Calumet-Sag Trail) runs for 16.2 miles and connects several communities and additional trails, as well as providing access to scenic forest preserves and secluded...
 IL 16.2 mi Asphalt
Illinois’ Centennial Trail runs 13-miles through parts of three suburban counties from Willow Springs Road to Romeo Road/135th Street southwest of Chicago. About the Route The trail occupies a...
 IL 13 mi Asphalt
The Chicago Lakefront Trail is aptly named; it spans 19 miles along the shore of Lake Michigan, going right through downtown Chicago to pass many cultural and tourist attractions throughout the...
 IL 19 mi Asphalt, Concrete
The Erie Lackawanna Trail runs for 17.6 miles and connects Crown Point and Hammond, two former rail junctions whose early fortunes were tied to the tracks carrying people and goods to and from...
 IN 17.6 mi Asphalt
The Erie Trail (otherwise known as the North Judson Erie Trail) occupies the railbanked right-of-way of the former JK Line Railroad, running over eleven miles from downtown North Judson southeast to...
 IN 11.1 mi Asphalt
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...
 IL 3.7 mi Asphalt
The Illinois Prairie Path (IPP) was one of the nation’s first rail-trail conversions. The 58-mile trail consists of five connected trail segments with three main branches that converge at 300 S...
 IL 58.52 mi Asphalt, Concrete, Crushed Stone
The Indiana Michigan River Valley Trail connects the towns of Niles, MI, and Mishawaka, IN via. 17 miles of paved multi-use trails. The trail passes different sites like Notre Dame University as well...
 MI 17.5 mi Asphalt, Concrete
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...
 IN 2.4 mi Asphalt
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...
 IL 8.9 mi Asphalt
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...
 IN 3.1 mi Asphalt
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...
 IL 7.6 mi Asphalt
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...
 IN 0.6 mi Asphalt
The North Branch Trail follows the North Branch of the Chicago River for 25.5 miles through Cook County. The trail was originally a dirt path often used for horseback riding; though it’s now paved, an...
 IL 25.5 mi Asphalt
The North Shore Channel Trail extends 8.3 miles from the junction of Green Bay Road and McCormick Boulevard in northern Evanston to the junction of Lawrence Avenue and Francisco Avenue in...
 IL 8.3 mi Asphalt, Concrete, Dirt
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...
 IL 1 mi Asphalt, Concrete
The Indiana Michigan River Valley Trail connects the towns of Niles, MI and Mishawaka, IN via. 17 miles of paved multi-use trails, some of which have their own unique identity. The trail also passes...
 IN 3 mi Concrete
First-time visitors to the Oak Savannah Trail might be surprised at the profusion of natural areas they’ll encounter as they travel the 10.3 miles between Hobart and Griffith in northern Indiana’s...
 IN 10.2 mi Asphalt
Running between the suburbs of Chicago Heights and Joliet, the Old Plank Road Trail runs for 21.6 miles and offers views of oak trees and sugar maples, prairie grasses, and wildflowers that peek up...
 IL 21.6 mi Asphalt
Accordion
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...
 IN 22.5 mi Asphalt
The Pennsy Greenway stretches between Calumet City, Illinois, and Schererville, Indiana. The trail begins at the southern end of the Burnham Greenway on the eastern edge of the Forest Preserve...
 IL, IN 14.5 mi Asphalt
Prairies and dunes are just two of the natural features trail users will experience on the Prairie Duneland Trail, located just a few miles south of the Lake Michigan shoreline and the Indiana Dunes...
 IN 10.3 mi Asphalt
The Indiana Michigan River Valley Trail connects the towns of Niles, MI and Mishawaka, IN via. 17 miles of paved multi-use trails, some of which have their own unique identity. The trail also passes...
 IN 3.4 mi Asphalt
Leave the cars at home: the Route 30 Bike Path gives users an alternative way to travel from the Village of Frankfort in the east, through Mokena to New Lenox in the west, a distance of over 7.5...
 IL 7.6 mi Asphalt
Closure Notice: Starting 05/01/2023 through 12/31/2026, there will be intermittent trail closures under the Tri-State Tollway (I-294) bridge, spanning from Ogden Ave to 31st St due to ongoing...
 IL 28.6 mi Asphalt, Cinder, Woodchips
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....
 IL 2 mi Asphalt
The Thorn Creek Trail offers a paved route traversing woodlands abundant with wildlife through several communities on the southern outskirts of Chicago.  The trail travels from Brownwell Woods in...
 IL 17.2 mi Asphalt
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,...
 IL 24 mi Asphalt
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...
 IL 3.6 mi Asphalt
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...
 IL 1.1 mi Asphalt
Although just shy of three miles, the Veterans Memorial Trail provides a wooded, paved trail experience for residents in the Chicago suburbs of Romeoville, Lemont, and Woodridge. Those seeking a...
 IL 2.7 mi Asphalt
When complete, the Veterans Memorial Trail will stretch close to 12 miles, connecting a series of memorials honoring US veterans from every era. At present, 1.9 miles are complete and usable, located...
 IN 1.9 mi Asphalt
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...
 IL 5.3 mi Asphalt
The Coal Line Trail runs along the abandoned Notre Dame & Western Railroad coal line, which used to deliver coal to the Notre Dame Power Plant. Developing in stages, the route primarily uses the old...
 IN 1.5 mi Concrete
The Dunes Kankakee Trail is a 1.8-mile walking and bike path that carries trail users throughout Indiana Dunes National Park.  Starting at the trail's southern endpoint just outside the park at the...
 IN 1.8 mi Asphalt
The Indiana Michigan River Valley Trail connects the towns of Niles, MI and Mishawaka, IN via. 17 miles of paved multi-use trails, some of which have their own unique identity. The trail also passes...
 IN 1.7 mi Asphalt, Concrete
The 6.5-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...
 IL 6.5 mi Asphalt, Concrete, Crushed Stone
The Indiana Michigan River Valley Trail connects the towns of Niles, MI and Mishawaka, IN via. 17 miles of paved multi-use trails, some of which have their own unique identity. The trail also passes...
 IN 3.5 mi Asphalt
The Little Calumet River Levee Trail zig-zags east-west between Gary and Munster in Lake County, bringing residents to the river and its wetlands, and offering ample opportunities for birding and...
 IN 13 mi Asphalt
The Mishawaka Riverwalk is a multiuse loop trail that winds along both banks of the St. Joseph River for 2.6 miles in the City of Mishawaka. Pedestrian bridges provide connections between the...
 IN 2.6 mi Asphalt, Brick, Concrete
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...
 IN 4.4 mi Asphalt
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...
 IL 6.7 mi Asphalt, Boardwalk, Concrete, Gravel
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....
 IL 3 mi Asphalt, Concrete
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...
 IL 1.2 mi Asphalt
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...
 IL 22.3 mi Asphalt, Crushed Stone
Although its current length is just over a mile, the small-but-mighty Chessie Trail will connect several parks in the northwestern Indiana city of La Porte. At its northern end, the paved pathway...
 IN 1.45 mi Asphalt, Concrete
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...
 IL 0.1 mi Asphalt
The community of Granger is tucked into the north end of Indiana, bordering Michigan. The community itself, through the Friends of Granger Paths recognized the need for safe, separate areas for...
 IN 5 mi Concrete
The Vale Park West Pathway is a multiuse trail in the Chicago suburb of Valparaiso. At 0.7 mile long, the trail passes through a mix of woodland and prairie, as well as over a creek on a 220-foot...
 IN 0.7 mi Concrete
Following a former rail corridor for less than a mile through Lake Station, the Fairview Walking Trail is a flat and paved multiuse path. The rail-trail runs through a small linear park in a...
 IN 0.7 mi Asphalt
The Lake Max Trail follows a former rail corridor south through Culver and provides new community connections. Eight- to ten-feet-wide with a surface of concrete and asphalt, the multi-use trail is...
 IN 1.63 mi Asphalt, Concrete
The Lincoln Memorial Trail is a 1.8-mile multiuse path in the community of Westville, which is located just 15 minutes from Lake Michigan in Indiana's La Porte County.  The southwest trailhead on...
 IN 1.8 mi Asphalt, Concrete
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...
 IL 2 mi Asphalt
The Preservation Path is a two-mile paved trail in the community of Matteson, Illinois. The path begins on Vollmer Road and terminates at the Old Plank Road Trail. The trail is paved with center...
 IL 2.1 mi Asphalt
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...
 IN 0.8 mi Asphalt
The Indiana Michigan River Valley Trail connects the towns of Niles, MI and Mishawaka, IN via. 17 miles of paved multi-use trails, some of which have their own unique identity. The trail also passes...
 IN 0.6 mi Concrete

Recent Trail Reviews

North Shore Channel Trail

Could easily be improved; will it happen?

July, 2025 by n9jhh4vwpk

The pavement of the Chicago section between Foster north to Lincoln is in very rough shape, and has only deteriorated since I started using the trail regularly last September (2024). Another priority could/should be the addition of some bridge overpasses (more underpasses are probably not feasible) so that trail users could avoid having to cross several busy (and only getting busier) intersections from Devon all the way up and into Evanston. It has some really enjoyable sections, though, and some stretches in Lincolnwood/Skokie have been recently repaved.

read more …

Panhandle Pathway

now 23 miles

June, 2025 by bradtollefson

they've extended the trail north in winamac from 11th to 17th Street. adding a half mile to the trail.

read more …

Illinois Prairie Path

Great ride

June, 2025 by ricter87

Rode part of the Prairie Part starting in Warrenville a couple of days after substantial rain in June 2025. The trail had some very minor puddles but was in great shape. When in Warrenville don’t miss the great bike shop where I got some excellent advice about which way to go on the trail. Highly recommend this route. Thanks to the bike shop guys!

read more …
Accordion

Northerly Island Trail

it’s cool,

June, 2025 by mrjocasio

It’s not the ideal path, but to see the city from a different perspective, it’s cool. Little confusing to maneuver, but it’s cool. Nice beach on one side. I like it. I recommend it, but can be confusing.

read more …

Des Plaines River Trail

very confusing

June, 2025 by mrjocasio

I did this trail on bike 2 years ago and I hated it, signage is terrible, at one point after Golf road, you literally come to an end and have to carry your bike over train tracks and active train tracks. No signs of any sort. You go through a campground that confuses you even more. I won’t do it again. To ridiculous.

read more …

North Shore Channel Trail

not the best

June, 2025 by mrjocasio

Like other reviews, I agree too many red lights that take forever to change, the smell of the garbage plant near by stinks, it’s an ok trail to walk but bike ride, no. You’ll be done in 20 minutes. From Devon to Greenbay road. I give it 2 stars for riding 4 for walking.

read more …

Chicago Lakefront Trail

my favorite place in the world

June, 2025 by mrjocasio

I do this trail at least 3 times a week, it’s a beautiful trail. You can get lost if you don’t know it. Stick to the trail close to drive. I know it all too well so I don’t get lost. But the scenery coming around the corner of Fullerton is just spectacular, the view north from the museum campus is amazing. I love this trail and it’s my comfort zone.

read more …

Erie Lackawanna Trail

Trail is closed at Rt. 30 heading North from Erie Lackwana trailhead.

June, 2025 by tduffmcg3623

Trail is closed at Rt. 30 heading North from Erie Lackwana trailhead.

read more …

LaSalle Trail

Good Tail

June, 2025 by clonetrooper5373

It has a nice round trip, with mostly smooth pavement except by Roseland park, so maybe skip that section.

read more …

Mishawaka Riverwalk

Okay

June, 2025 by clonetrooper5373

It's an okay trail with a nice round trip, and some enjoyable sights.

read more …

Coal Line Trail

Very Nice

June, 2025 by clonetrooper5373

Nice and open to nature with a brief urban stint with not too many road crossings.

I would recommend this trail to anyone looking.

read more …

Northside Trail

Okay

June, 2025 by clonetrooper5373

It's mostly an urban trail, with not too much nature.

Geese were allover the place and so was their poop.

Good round trip though.

read more …
View more reviewsView fewer reviews

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