Waukegan, IL Horseback Riding Trails and Maps

1540 Reviews

Looking for the best Horseback Riding trails around Waukegan?

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

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Activities
Length
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14 Results
Activities
Length
Surfaces
Type

Danada and Herrick Lake Regional Trail

5.8 mi
State: IL
Crushed Stone

Des Plaines River Trail

56.1 mi
State: IL
Asphalt, Crushed Stone, Dirt, Gravel

Great Western Trail (DeKalb, Kane)

18 mi
State: IL
Asphalt, Crushed Stone

Great Western Trail (DuPage)

12.7 mi
State: IL
Crushed Stone

Hebron Trail

6.7 mi
State: IL
Crushed Stone, Gravel

Illinois Prairie Path

58.52 mi
State: IL
Asphalt, Concrete, Crushed Stone

Millennium Trail (IL)

30.7 mi
State: IL
Asphalt, Concrete, Crushed Stone

North Branch Trail

25.5 mi
State: IL
Asphalt

Prairie Trail (IL)

26.4 mi
State: IL
Asphalt, Crushed Stone, Dirt, Gravel

Waterfall Glen

9.5 mi
State: IL
Crushed Stone, Grass

West Branch DuPage River Trail

26 mi
State: IL
Gravel

White River State Trail

19.7 mi
State: WI
Concrete, Crushed Stone, Gravel

Muskego Recreation Trail

7.5 mi
State: WI
Crushed Stone, Dirt, Gravel

Pelishek-Tiffany Nature Trail

6 mi
State: WI
Dirt, Grass
Trail Image Trail Name States Length Surface Rating
This regional trail connects two of DuPage County's forest preserves—Herrick Lake and Danada—on a crushed stone pathway nearly 6 miles long. Together, the preserves cover more than 1,600 acres of...
IL 5.8 mi Crushed Stone
The Des Plaines River Trail runs alongside the Des Plaines River for just over 56 miles, protecting watershed habitat and forestland through much of Lake and Cook Counties. The trail is a natural...
IL 56.1 mi Asphalt, Crushed Stone, Dirt, Gravel
The western segment of the Great Western Trail in Illinois follows 18 miles of a former railway corridor through DeKalb and Kane counties, between Sycamore Forest Preserve in the City of Sycamore and...
IL 18 mi Asphalt, Crushed Stone
The eastern segment of the Great Western Trail in Illinois follows almost 13 miles of an abandoned railway corridor through DuPage County, between Villa Park and West Chicago. About the...
IL 12.7 mi Crushed Stone
The Hebron Trail rolls across the northern Illinois prairie through the former corridor of the Kenosha and Rockford Railroad, known as the Kenosha Division Line at the time of its demise in 1939....
IL 6.7 mi Crushed Stone, Gravel
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 Millennium Trail spans just over 30 miles in two disconnected segments. The trail goes through forest, farmland, and the suburban neighborhoods of Lake County with a range of surfaces, including...
IL 30.7 mi Asphalt, Concrete, Crushed Stone
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 Prairie Trail runs the length of McHenry County and is managed by the McHenry County Conservation District. The rail trail spans just over 26 miles from the Wisconsin border and the farms and...
IL 26.4 mi Asphalt, Crushed Stone, Dirt, Gravel
The trail system in Waterfall Glen Forest Preserve makes a loop around the entire park and totals 9.5 miles. About the Route The Waterfall Glen Forest Preserve is geologically significant,...
IL 9.5 mi Crushed Stone, Grass
The West Branch DuPage River Trail is a 26-mile regional trail that stretches between the North Central DuPage Regional Trail at its northern end and the DuPage River Trail at its southern end. The...
IL 26 mi Gravel
The White River State Trail is a 19.7-mile trail composed of two separate segments: a 12-mile stretch that runs between Elkhorn and just west of Burlington in Walworth County, and a 7-mile section...
WI 19.7 mi Concrete, Crushed Stone, Gravel
The Muskego Recreation Trail follows a corridor originally used by the Milwaukee Electric Railway & Light, an interurban railroad in southeastern Wisconsin. The corridor was later acquired by...
WI 7.5 mi Crushed Stone, Dirt, Gravel
The Pelishek-Tiffany Nature Trail runs for 6 miles along an abandoned railroad corridor, between the towns of Allens Grove and Clinton. The trail is open to snowmobiles, cyclists, horseback riders and...
WI 6 mi Dirt, Grass

Recent Trail Reviews

Prairie Farms Trail

Bumpy Ride

October, 2026 by kriekkoff_tl

It appeared that a load of crushed stone was recently added to the trail. A grader was used to level and spread out the stone, but ruts were left by the truck tires and the grader making the ride a little too bumpy unless you hugged the side of the trail where the grader did not reach. I enjoyed the route which meandered through cornfields, woods and prairie. The ride was peaceful, but there was no shade and I had to swat a few mosquitos when I stopped. There was an 8-car asphalt parking lot with porta potty near the north end of the trail that was not listed in TrailLink.

Ice House Trail

Nice Short Trail

October, 2026 by kriekkoff_tl

The 12-foot-wide asphalt surface had some tree root-raised areas, but manageable. The middle section of the route was a nicely paved road dedicated to wastewater treatment plant traffic. The southwestern section of the trail was nestled nicely behind backyards. The sides of the trail were mowed and the trail corridor itself was not only spacious, but nicely captured beneath a canopy of trees. The trail was a little out of the way, but I highly recommend it if you happen to be in the area.

Glacial Drumlin State Trail

Beautiful sunny October ride

October, 2026 by redpine2001

Completed my final leg of this trail by riding from London to Cottage Grove today. Trail conditions were very good, however the bridges can use some maintenance. All have matting across them to assist in preventing flats, however watch your approach, there can be some serious bumps getting onto & off the bridges. Having ridden the entire trail now, eastern portion several times; it’s just my opinion that the western portion would be my recommendation. East of Douseman the trail is paved, however much of it is in need of maintenance to remedy cracks.

Accordion

White River State Trail

Pleasant Surprise

September, 2026 by dsjr2

Scenic, very pleasant ride today. Farmland, lots of bridges, packed gravel so no surprises. Parked at the Elkhorn trailhead and biked to Burlington and back. Note: the DNR site says there's a bridge out, as of 9/27/26 - there are no bridges out. Really nice ride and great way to spend a 70 degree and sunny day in late September.

Fox River Trail (IL)

Wonderful Trail

September, 2026 by nevogamer_tl

We rode the Fox River Trail over two days in September 2026. We did a short ride from St Charles to South Elgin and back one the first day, followed by a ride to Aurora and then on to part of the Illinois Prairie Path before returning to St Charles. The trail was in excellent shape and, for the most part, was well marked. We thought the scenery was better going south, with lots of water fowl, flowers and points of interest to enjoy. This trail lived up to its expectations.

Robert McClory Bike Path

September 2026 Ride

September, 2026 by dpott

I just rode from my Chicago home to Racine on the North Shore Channel, Green Bay, R McClory and Kenosha County trails. The McClory is newly paved and well signed from the Great Lakes Naval Station north to the state line. There are no facilities other than the occasional bench, and there are long stretches without any shade. Otherwise it is a terrific ride!

Kenosha Pike Bike Trail

Spectacular Lake Views

September, 2026 by kriekkoff_tl

The trail starts unassumingly in a residential neighborhood to the north and winds its way through Carthage College before bursting out of a canopy of trees into a spectacular, unobstructive view of Lake Michigan. The trail hugs the coast and meanders through a series of gorgeous parks. Just when your senses have almost reached their limit, you find yourself riding along Harbor Park filled with an assortment of sculptures, museums, and marinas. The Park is electric!
This was the most enjoyable ride I have ever taken. I will be back!
There are two cautionary notes, however.
1. The city roads between Poerio Park West and upper Alford Park are in horrible condition. Maybe avoid this northern section altogether.
2. The trail that goes south from the 50th Street bridge as you enter the Harbor is actually a staircase. I missed it the first time, but realized it on my return. There is a very steep embankment with a thin bike path next to the stairs, if you want to risk it.

North Shore Trail (WI)

Short, flat and easy to ride

September, 2026 by kriekkoff_tl

The 10-foot wide asphalt surface is still in good shape. The trail hugs the road at the north end, but eventually disappears behind suburban backyards under a wonderful canopy of trees. There are a few pesky road crossings, but not bad. The trail is short, but flat and easy to ride. This is a great connector to the Kenosha County Bike Trail or the Kenosha Pike Bike Trail.

Millennium Trail (IL)

Hill Billy - Part 2

September, 2026 by kriekkoff_tl

I almost forgot to include this in my previous review:
If you do not like hills, DO NOT do either section of this trail.

Millennium Trail (IL)

Hill Billy

September, 2026 by kriekkoff_tl

Both the North and South sections used asphalt and crushed stone surfaces. Care must be taken when riding on the crushed stone. The trail is nearly 12 foot wide and it is neatly groomed, however, the stone is just loose enough to keep bicycle speeds down. The rider who tests their speed traveling downhill and around the blind curves will surely tumble. The age of the asphalt in both sections varies from "newer" to "desperately in need of repair." The southern section actually has a warning sign just south of Fairfield Park.
The last two miles of the northern section in Round Lake Beach is loaded with perpendicular cracks in the asphalt causing a jarring ride even at slow speeds.
One must be cautious at the street crossings although some of the busier roads have traffic lights with designated pedestrian cross walks. The signage was ok, but could have been better.

Robert McClory Bike Path

New Asphalt!

September, 2026 by kriekkoff_tl

Except for the 2 miles of crushed stone from Sheridan Road in Highland Park to County Line Road in Ravinia, the entire trail surface it asphalt!
The first 11 miles of the trail from the Wisconsin border is newer asphalt; no cracks or bumps to worry about. Just a smooth ride. The northern section of the bike path, however, is plagued with several street crossings, all of which must be approached with caution. There is little to no shade on the northern section.
The southern section of the bike path has a lot more points of interest including various sculptures along the trail, Metra train stations, the Ravinia Festival grounds and interesting cities to explore. The southern section offers much more shade, but also has a few street crossings as well.
The trail does give way to the road in both sections, but the signage is good for the most part. There are new mile markers on the west side of the trail every 1/2 mile.

Muskego Recreation Trail

Nice East-West Corridor

September, 2026 by kriekkoff_tl

The surface of this 8-foot wide trail seems to be crushed stone over an older asphalt base. It is a little tougher to ride than the typical crushed gravel surface. There are some "soft" spots throughout the length of the route, but still manageable. The trail is relatively flat with an occasional grade change. The scenery is mostly suburban backyard with a touch of industrial to the west. There is very little shade to protect you from the sun, but the openness is refreshing. Although most street crossings have minimal traffic, please take caution when approaching them. This is one of my "go to" rides.

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Accordion

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