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 71 trails covering 4449 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

Bloomingdale Trail (The 606)

There and back is 5.4 miles

April, 2024 by breadbrowder

Beautiful but beware of pollen.

Spring Creek Greenway Trail

great running trail

March, 2024 by ielpmike

This is a really great trail to run on. It is very soft, especially the stretch just east of Gougar. There is a lot of really beautiful scenery. I ran the entire trail today and it was exactly 7 miles. This is not a good place to ride a bike unless you enjoy riding a soft soggy trail. There are horses on this trail so be sure to keep dogs on a leash. Just as side note, there are two dogs that run around loose from a local house. But they are totally friendly. They have run up to me twice now. They’re just tail wagers. and sniffers.

Cal-Sag Trail

New CalSag Closure 127th St. Bridge

February, 2024 by tom h

Announced last week is the closure of the 127th St. bridge which is located just east of CalSag Road. This will take place from March to December, 2024. Or in other words, the whole biking season for 2024. The repair of the intersection at 127th and CalSag road was completed in late 2023.

Accordion

Chesapeake and Ohio Greenway

great trail

February, 2024 by peggymj

I rode this on 2/26/24 a beautiful 70 degree day This trail runs from merrillville all the way to the Oak Savannah Prairie Park and connects to the Oak Savannah Trail - north to Griffith and south to Schererville and Crown Point

Green Bay Trail

Nicely Maintained but Poor Signage

February, 2024 by reg16

The Green Bay trail is nicely maintained but as others have mentioned the signs for how to keep the trail when going through residential areas is confusing. We found ourselves at one point randomly biking through Highland Park.

Tinley Creek Trail (North)

BEAUTIFUL

November, 2023 by scottlarry7722_tl

OMG AMAZING PLACE TO WALK

Granger Paths

side walks to everywhere

October, 2023 by jrm2024

This is a great bike path to connect the community and keep children out of street.

Wauponsee Glacial Trail

Very Clean, Quiet, Flat & Easy ride for all

October, 2023 by kimlogan

We wanted to start at the very beginning of the trail. We parked in the parking lot of the Jehovah Witness Kingdom Hall with no problems. To get to the trail from there you will have to ride on the street about 2 blocks so be careful of cars. The first three miles of the trail are asphalt paved but there are numerous locations that have either buckled or have tree roots that are pushing up; so this has caused there to be some pretty intense bumps along the way. No worries about this…just try to avoid them because after about mile 2.5 they completely go away. Not sure exactly what mile mark but the asphalt changes to a smooth and easy to ride limestone path. There are a few bridges that you ride across so those are decent photo ops. There is not a whole lot to

Illinois & Michigan Canal State Trail

Janet

September, 2023 by janet koch

Don't bother. Trail is still closed and the canal has been drained. The wildlife is gone and the trail not maintained. This is why I gave it a one star rating. There isn't a zero rating which it deserves.

Illinois & Michigan Canal State Trail

its okay

September, 2023 by joannamaciej

I basically drove from romeoville to morris halfway from morris i started to feel like this trail was not safe when you get out from the woods park west and the bridge is gone in morris so just avoid the trail going to seneca

Panhandle Pathway

A quiet ride

September, 2023 by robert.richter89

The Panhandle Pathway is flat, secluded, has a few trailheads for easy access and there are two towns where you can easily grab something to eat (Royal Center and Winimac). The scenery might be a bit monotonous but in this case I found it serene rather than a detriment. Mileage is printed in tenth of a mile increments on the nearly perfect asphalt surface.

I rode the entire 21.5 mile length starting in Winimac heading towards Kenneth. It was an overcast weekday so I only saw one other cyclist on my entire out and back. There are many small road crossings but most of them had no traffic so I don't count that as a negative. I stopped for lunch in Royal Center which was a quick turn off from the trail.

If you are looking for a trial with varied scenery or challenging hills the Panhandle Pathway does not offer it. If you are looking for a quiet, relaxing ride through bucolic farmland the Panhandle Pathway delivers.

Wauponsee Glacial Trail

Wauponsee Glacial Trail Ride

September, 2023 by dynomight

My husband and I rode this trail on 9/4/2023 and enjoyed our ride. Trail is crushed limestone and is in decent condition. The trail is more sun than shade so take that into account when riding. There are places along the way to stop if needing a restroom or water.

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