Looking for the best trails around Highland Park?

Explore the best rated trails in Highland Park, IL. Whether you're looking for an easy walking trail or a bike trail like the Illinois & Michigan Canal State Trail and Tall Grass Greenway Trail. With more than 121 trails covering 4977 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

East Northbrook Trail

Great connector trail

December, 2022 by billymac72

This trail begins off of Voltz near Sunset Ridge and goes about a mile and a half or so across Sunset up to Dundee Rd. If riding through Northbrook, it's a very handy way to avoid Skokie Blvd and make your way up to the North Trail entrance off of Dundee across from Botanic Gardens. It's mostly just a nice, secluded, wooded, but paved strand behind some residential neighborhoods and runs parallel to Skokie. When riding, please be a little more mindful of residents walking, often with dogs and children. It doesn't get very crowded, and people generally aren't expecting bikers like on the major trails.

North Shore Channel Trail

north shore trail

November, 2022 by lrios28822

This trail continues for 10 miles , 20 miles round trip. I start the trail at Belmont ave by Clark Park and continue thru new connection over Addison Ave continue thru Horner Park . You can travel on Manor Ave to enter the trail at Lawrence Ave and connect to the trail on Argyle. I continue the. Trail thru Green Bay Road . I am able to ride the trail their and back usually in 90 to 100 minutes . Excellent trail not very busy , I have been riding five times a week for 3 months Lou

Middlefork Savanna Trail

Beautiful Prairie Trail

November, 2022 by erossen22

A great place for walkers, hikers, bikers, and families. It’s been wonderfully restored and brings nice surprises during each season.

Accordion

Old Plank Road Trail (IL)

Repaved from Harlem Ave. to Schoolhouse Rd.

October, 2022 by wheelzbat

This has been long overdue. From Harlem Ave. in Frankfort to Schoolhouse Rd. in New Lenox is getting resurfaced. As of 10/26/2022 Harlem to Wolf Rd. in Frankfort is complete. Now if they could resurface the rest too, it would be a 5 star trail.

Wauponsee Glacial Trail

Rode from Ballou to Manhattan, 2p mile round trip. TraIl is in excellent condition. Yrsil has a nice wind break on both sides of the trail for almost all of the ride. Will rode again.

October, 2022 by kimjim425

Rode from Ballou to Manhattan, 2p mile round trip. TraIl is in excellent condition. Yrsil has a nice wind break on both sides of the trail for almost all of the ride. Will rode again.

Centennial Trail (IL)

one of the best

October, 2022 by daniel.shaw813

They just replaced the first 4ish miles that start in Willow springs to the bridge, a serious game changer, the last three miles near lemont have bumps in the trails but that’s what happens when you build on a wetland near a river. freeze thaw expansion… the brewery at the end the best part

Hebron Trail

Nice trail for getting in a quick bike ride

October, 2022 by ktgranzow1

I had ridden the northern end of the Prairie trail & saw the sign forg the Hebron trail so decided one day to check it out. Rode from the Prairie Trail junction to the “trail end” at Lange Road & back again. About an hour round trip but that included stopping to take photos. It’s a well groomed trail, plenty wide for comfortable passing of others. West of Keystone Road crossing is pretty much straight & flat but scenery still varies.

DuPage River Trail

A Pleasant Trail thru Parks and on City Streets

October, 2022 by buehler868

This trail is a nice one if you are looking for something other than a super straight rails to trails corridor. I parked at the nearby and beautiful DuPage County St James Forest Preserve and took a connecting trail to the start of the officially named West Branch DuPage River Trail that heads south. Most of the route is in Forest Preserves, alongside the West Branch of the DuPage River.
Once you come upon the spectacular Naperville Riverwalk, north of downtown Naperville which does not allow bikes, you must use city streets. That provides a nice variety. South of downtown the trail is again in parks. One can travel all the way south into Will County, with more options for connecting trails.

Salt Creek Trail (IL)

Great Trail for Wayfinding

September, 2022 by buehler868

In the Chicago suburban area, the Salt Creek Trail, at 27 miles long, is a great trail for what I like to do, which is cycling wayfinding. It’s not a rail to trails so the trail stiches together a variety of different segments in different surroundings: paved paths in forest preserves, separate paths along highways, gravel paths, subdivision roads and even a wood chip path. There are many connecting paths, so don’t expect a sign for every turn and that’s where wayfinding comes in. Use your TrailLink downloaded map and find your way. I made a few wrong turns but that’s part of wayfinding. I parked at Edgewater Park and did out and back rides, first to the south and then to the north. A fine 54-mile ride on a beautiful fall day. I even found two updates that are needed to the TrailLink map, which I will send to Rails to Trails Conservancy.

Des Plaines River Trail

south end not great

September, 2022 by william58

I started from the south entry point and only made it a few miles in before deciding to just take the roads back south. It hadn't rained for a few days and the bridge underpasses were still full of pooled water and soft mud. I don't even know if I'd ride through them on a mountain bike unless I was really looking to get nasty.

Oak Leaf Trail

Extension to Bender Park Open but not yet ready for Use

September, 2022 by buehler868

The Milwaukee County Parks, Oak Leaf Trail webpage says the extension of the South Shore Line segment is open to Bender Park. It is not yet show on the TrailLink map. On my September 2022 trip up to the Oak Leaf Trail, to do the original South Shore Line and the Oak Creek Line, I decided to see what the new extension was like. Yes, it is open with routing signs in place and a creek bridge constructed. But the surface is made up of 1-inch sized crushed stone which is typically used as a base layer under asphalt pavement. Even though I have a gravel bike, from Drexel Ave I only made it down to Pennsylvania Ave and gave up the going further. It’s just too rough. I made the trip back using highways. I searched on the internet, and it seems that the funding grants describe a 2023 completion. I hope what is the case is the asphalt paving will be done in 2023.

Oak Leaf Trail

Riding the Southeast Quadrant

September, 2022 by buehler868

On my third trip up to the Oak Leaf Trail I did what I call the Southeast Quadrant. I parked at Greenlawn Park and did the trail and spurs down to the Racine County line and up to Cupertino Park near the Lake Michigan Ferry. What I liked about this trip was the variety in the trail. Segments consisted of rails to trails (with powerlines), trail in parks, separate trails on arterial streets, the parkway roads, and rural highways. The long, southerly segment in the forest on the bluffs along Lake Michigan was the prettiest segment of my three trips on the Oak Leaf Trail. The north segment along Lake Michigan was closer to the water and gave a nice view of downtown Milwaukee.
One concern is the trail is being extended to Bender Park, which is popular but what about funding of maintenance of the trail that already exists? This section had some of the asphalt showing its age with the periodic shrinkage cracks giving that frequent bothersome bump. One hidden path bridge at the bottom of a hill had plywood covering over rotted deck boards, which at speed was very rough. But none of these maintenance issues should stop any one from coming to use the Oak Leaf Trail. I do recommend stopping at the coffee/ice cream store the trail parkway passes at Chicago Ave.
I am sure the rail to trail segment from Greenlawn Park was the former North Shore Interurban Line (to Chicago) that my folks took on their honeymoon to Milwaukee in 1944.

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Accordion

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