Looking for the best trails around Chesterton?

Explore the best rated trails in Chesterton, IN, whether you're looking for an easy walking trail or a bike trail like the Illinois & Michigan Canal State Trail and Spring Creek Greenway Trail . With more than 72 trails covering 4461 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Recent Trail Reviews

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.

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!

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.

Accordion

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.

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.

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.

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.

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.

Mishawaka Riverwalk

Okay

June, 2025 by clonetrooper5373

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

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.

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.

Centennial Trail (IL)

First time on this trail

June, 2025 by diane connelly

I rode on this trail for the first time yesterday. It is well maintained, pretty shady, and has well placed maps. I will definately go again. I gave it 4 stars instead of 5 because there aren't any water sources at either end or along the trail. There are toilets (vault and a porta potty) at the ends, so that's a plus. At the Willow Springs end, about 2 blocks from the trail end, there's a Speedway gas station with snacks and beverages. You can see it from the trail. So if you go, make sure to bring plenty of water!

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