Winnetka, IL Horseback Riding Trails and Maps

1024 Reviews

Looking for the best Horseback Riding trails around Winnetka?

Find the top rated horseback riding trails in Winnetka, 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
Surfaces
Type
15 Results
Activities
Length
Surfaces
Type

Busse Woods Trail

11.2 mi
State: IL
Asphalt

Danada and Herrick Lake Regional Trail

5.8 mi
State: IL
Crushed Stone

Des Plaines River Trail

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

Fox River Trail (IL)

44.6 mi
State: IL
Asphalt, Concrete, Crushed Stone

Great Western Trail (DuPage County)

12 mi
State: IL
Crushed Stone

Great Western Trail (IL)

17 mi
State: IL
Asphalt, Crushed Stone

Hebron Trail

6.7 mi
State: IL
Crushed Stone, Gravel

Illinois Prairie Path

58.4 mi
State: IL
Asphalt, Concrete, Crushed Stone

Millennium Trail

30.7 mi
State: IL
Asphalt, Concrete, Crushed Stone

North Branch Trail

21.3 mi
State: IL
Asphalt

Prairie Trail (IL)

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

Timber Ridge Trail

1 mi
State: IL
Gravel

Waterfall Glen

9.5 mi
State: IL
Crushed Stone, Grass

Wauponsee Glacial Trail

22.3 mi
State: IL
Asphalt, Crushed Stone

White River State Trail

19 mi
State: WI
Concrete, Crushed Stone, Gravel
Trail Image Trail Name States Length Surface Rating
The Busse Woods Trail system is located within Ned Brown Forest Preserve, a 3,700-acre property in the northwestern suburbs of Chicago. There are 11.2 miles of paved trails for cyclists, equestrians...
IL 11.2 mi Asphalt
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 56.2 mi Asphalt, Crushed Stone, Dirt, Gravel
The the Fox River Trail (FRT) was built on stretches of three former railroads: Chicago, Aurora & Elgin;  Aurora, Elgin, & Fox River Electric; and Chicago & North Western. Today, it hosts a multitude...
IL 44.6 mi Asphalt, Concrete, Crushed Stone
The eastern segment of the Great Western Trail in Illinois follows 12 miles of an abandoned railway corridor through DuPage County, between Villa Park and West Chicago. There are plans to extend the...
IL 12 mi Crushed Stone
The western segment of the Great Western Trail in Illinois follows 17 miles of a former railway corridor through DeKalb and Kane counties, between LeRoy Oakes Forest Preserve and the town of Sycamore....
IL 17 mi Asphalt, 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. It consists of five connected trail segments with three main branches that converge at Volunteer Park (West...
IL 58.4 mi Asphalt, Concrete, Crushed Stone
The Millennium Trail currently spans just over 30 miles in two disconnected segments, but there are plans to extend it to 35 miles and connect it to the Des Plaines River Trail. The trail goes through...
IL 30.7 mi Asphalt, Concrete, Crushed Stone
The North Branch Trail follows the North Branch of the Chicago River over 20 miles through Cook County. The trail was originally a dirt path often used for horseback riding; though it’s now paved, an...
IL 21.3 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 26.5 mi Asphalt, Crushed Stone, Dirt, Gravel
The Timber Ridge trail is located on the eastern side of the Timber Ridge Forest Preserve in west Chicago. The preserve offers several trails, fishing, picnicking, and is home to Kline Creek Farms,...
IL 1 mi Gravel
The trail system in Waterfall Glen Forest Preserve makes a loop around the entire park. The preserve is geologically significant, featuring glacier-carved rock ridges, ravines and wetland potholes,...
IL 9.5 mi Crushed Stone, Grass
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
The White River State Trail is 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 that connects the...
WI 19 mi Concrete, Crushed Stone, Gravel

Now, More Than Ever, Trails Matter!

During COVID-19, trails are being counted on as places where people can find solace and respite and we need your support to keep trails open and provide these critical FREE resources! Please continue to practice physical distancing and check the status of your trail before heading out!

Trails by activity

Fox River Trail (IL)

IL - 44.6 miles

The the Fox River Trail (FRT) was built on stretches of three former railroads: Chicago, Aurora & Elgin;  Aurora, Elgin, & Fox River Electric; and Chicago & North Western. Today, it hosts a multitude...

Millennium Trail

IL - 30.7 miles

The Millennium Trail currently spans just over 30 miles in two disconnected segments, but there are plans to extend it to 35 miles and connect it to the Des Plaines River Trail. The trail goes through...

Busse Woods Trail

IL - 11.2 miles

The Busse Woods Trail system is located within Ned Brown Forest Preserve, a 3,700-acre property in the northwestern suburbs of Chicago. There are 11.2 miles of paved trails for cyclists, equestrians...

White River State Trail

WI - 19 miles

The White River State Trail is 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 that connects the...

Accordion

North Branch Trail

IL - 21.3 miles

The North Branch Trail follows the North Branch of the Chicago River over 20 miles through Cook County. The trail was originally a dirt path often used for horseback riding; though it’s now paved, an...

Great Western Trail (IL)

IL - 17 miles

The western segment of the Great Western Trail in Illinois follows 17 miles of a former railway corridor through DeKalb and Kane counties, between LeRoy Oakes Forest Preserve and the town of Sycamore....

Great Western Trail (DuPage County)

IL - 12 miles

The eastern segment of the Great Western Trail in Illinois follows 12 miles of an abandoned railway corridor through DuPage County, between Villa Park and West Chicago. There are plans to extend the...

Wauponsee Glacial Trail

IL - 22.3 miles

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...

Danada and Herrick Lake Regional Trail

IL - 5.8 miles

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...

Des Plaines River Trail

IL - 56.2 miles

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...

Timber Ridge Trail

IL - 1 miles

The Timber Ridge trail is located on the eastern side of the Timber Ridge Forest Preserve in west Chicago. The preserve offers several trails, fishing, picnicking, and is home to Kline Creek Farms,...

Prairie Trail (IL)

IL - 26.5 miles

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...

Illinois Prairie Path

IL - 58.4 miles

The Illinois Prairie Path (IPP) was one of the nation’s first rail-trail conversions. It consists of five connected trail segments with three main branches that converge at Volunteer Park (West...

Prairie Trail (IL)

IL - 26.5 miles

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...

Des Plaines River Trail

IL - 56.2 miles

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...

Fox River Trail (IL)

IL - 44.6 miles

The the Fox River Trail (FRT) was built on stretches of three former railroads: Chicago, Aurora & Elgin;  Aurora, Elgin, & Fox River Electric; and Chicago & North Western. Today, it hosts a multitude...

Wauponsee Glacial Trail

IL - 22.3 miles

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...

Accordion

White River State Trail

WI - 19 miles

The White River State Trail is 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 that connects the...

North Branch Trail

IL - 21.3 miles

The North Branch Trail follows the North Branch of the Chicago River over 20 miles through Cook County. The trail was originally a dirt path often used for horseback riding; though it’s now paved, an...

Hebron Trail

IL - 6.7 miles

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....

Great Western Trail (DuPage County)

IL - 12 miles

The eastern segment of the Great Western Trail in Illinois follows 12 miles of an abandoned railway corridor through DuPage County, between Villa Park and West Chicago. There are plans to extend the...

Great Western Trail (IL)

IL - 17 miles

The western segment of the Great Western Trail in Illinois follows 17 miles of a former railway corridor through DeKalb and Kane counties, between LeRoy Oakes Forest Preserve and the town of Sycamore....

Waterfall Glen

IL - 9.5 miles

The trail system in Waterfall Glen Forest Preserve makes a loop around the entire park. The preserve is geologically significant, featuring glacier-carved rock ridges, ravines and wetland potholes,...

Busse Woods Trail

IL - 11.2 miles

The Busse Woods Trail system is located within Ned Brown Forest Preserve, a 3,700-acre property in the northwestern suburbs of Chicago. There are 11.2 miles of paved trails for cyclists, equestrians...

Millennium Trail

IL - 30.7 miles

The Millennium Trail currently spans just over 30 miles in two disconnected segments, but there are plans to extend it to 35 miles and connect it to the Des Plaines River Trail. The trail goes through...

Illinois Prairie Path

IL - 58.4 miles

The Illinois Prairie Path (IPP) was one of the nation’s first rail-trail conversions. It consists of five connected trail segments with three main branches that converge at Volunteer Park (West...

Danada and Herrick Lake Regional Trail

IL - 5.8 miles

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...

Timber Ridge Trail

IL - 1 miles

The Timber Ridge trail is located on the eastern side of the Timber Ridge Forest Preserve in west Chicago. The preserve offers several trails, fishing, picnicking, and is home to Kline Creek Farms,...

Busse Woods Trail

IL - 11.2 miles

The Busse Woods Trail system is located within Ned Brown Forest Preserve, a 3,700-acre property in the northwestern suburbs of Chicago. There are 11.2 miles of paved trails for cyclists, equestrians...

Great Western Trail (DuPage County)

IL - 12 miles

The eastern segment of the Great Western Trail in Illinois follows 12 miles of an abandoned railway corridor through DuPage County, between Villa Park and West Chicago. There are plans to extend the...

Waterfall Glen

IL - 9.5 miles

The trail system in Waterfall Glen Forest Preserve makes a loop around the entire park. The preserve is geologically significant, featuring glacier-carved rock ridges, ravines and wetland potholes,...

Illinois Prairie Path

IL - 58.4 miles

The Illinois Prairie Path (IPP) was one of the nation’s first rail-trail conversions. It consists of five connected trail segments with three main branches that converge at Volunteer Park (West...

Accordion

Danada and Herrick Lake Regional Trail

IL - 5.8 miles

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...

Timber Ridge Trail

IL - 1 miles

The Timber Ridge trail is located on the eastern side of the Timber Ridge Forest Preserve in west Chicago. The preserve offers several trails, fishing, picnicking, and is home to Kline Creek Farms,...

Fox River Trail (IL)

IL - 44.6 miles

The the Fox River Trail (FRT) was built on stretches of three former railroads: Chicago, Aurora & Elgin;  Aurora, Elgin, & Fox River Electric; and Chicago & North Western. Today, it hosts a multitude...

Prairie Trail (IL)

IL - 26.5 miles

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...

Hebron Trail

IL - 6.7 miles

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....

Millennium Trail

IL - 30.7 miles

The Millennium Trail currently spans just over 30 miles in two disconnected segments, but there are plans to extend it to 35 miles and connect it to the Des Plaines River Trail. The trail goes through...

North Branch Trail

IL - 21.3 miles

The North Branch Trail follows the North Branch of the Chicago River over 20 miles through Cook County. The trail was originally a dirt path often used for horseback riding; though it’s now paved, an...

Wauponsee Glacial Trail

IL - 22.3 miles

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...

Des Plaines River Trail

IL - 56.2 miles

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...

White River State Trail

WI - 19 miles

The White River State Trail is 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 that connects the...

Great Western Trail (IL)

IL - 17 miles

The western segment of the Great Western Trail in Illinois follows 17 miles of a former railway corridor through DeKalb and Kane counties, between LeRoy Oakes Forest Preserve and the town of Sycamore....

Recent Trail Reviews

Hebron Trail

perfect day

June, 2020 by nypeman

Rode from Hebron to Richmond and back. Signage could be better when you hit the railroad tracks but other than that small area the trail is well maintained. And a lovely phase 3 quarantine reopening outing!

Illinois & Michigan Canal State Trail

Always beautiful, but needs a little TLC this spring

June, 2020 by sarahccaltvedt

I'm writing this because we weren't able to find any information on current trail conditions. The I&M is one of our favorite trails in Northern Illinois. Today my husband and I rode between Channahon and Morris for the first time this season (now that they've finally re-opened the restrooms). We were pleased to see that it was not badly affected by recent flooding, but it definitely needs some maintenance. Between Au Sable and Morris there were three large holes which others had fortunately marked by putting large sticks in them. At Au Sable a tree limb is partially blocking the path at the west end of the park. Another rider said it had been there a week already. That section also hasn't been mowed yet, so the trail seems even narrower than usual. At Morris, we hoped to continue west. We knew there was a break in the trail and that you're supposed to be able to ride around the break on the street, but there was no signage or any other indication of how to do that, so we had to turn around when we came to a barrier. Also at Morris, be aware that the road bridge leading from town into Governor Stratton State Park on the east end is being replaced. You can either carry your bike down steps to the park or walk it around the barricades very carefully (at least on a Sunday when they're not working). East of Au Sable, the trail edges have been mowed, which is a good thing, because you need to watch for large wash-out holes on the canal edge. I know it's been a rough spring in terms of both weather and the pandemic, but I hope that the IDNR will be able to get the trail back in good shape again soon. It's a real treasure.

Old Plank Road Trail

Painful on a Road Bike

May, 2020 by childs80

I love the OPRT and have been riding it for 15+ years. Much of it is tree lined, and as a result, has some roots pushing up the pavement here and there. If your on a road bike around 15 mph, keep your eyes open, especially West of Cedar. They do a great job maintaining it, but you can’t keep every bump fixed. But other than that, this is an awesome beautiful trail.

Accordion

Green Bay Trail

Memorial Day Ride

May, 2020 by sagrosso2

The first part of the trail was really nice with paved paths. Sometimes it can be hard to follow the path but luckily I found other bikers to lead the way. Once you hit Glencoe it’s not paved so if it’s rained a lot recently chances are you’ll go through mud. It was cool following the Metra train line and passing Ravinia.

Busse Woods Trail

Bike riding

May, 2020 by friends4ever_079

I love this trail! I’ve been here 2 weekends in a row. One weekend with a 7 and 12 year old and the next weekend with my uncle. It’s a trail great for all ages. The kids loved going down the hill on the bridge and seeing the Elk. The trail is smooth, very scenic and beautiful.

Lake Michigan Pathway

Lake Michigan Pathway

May, 2020 by tangneygp

Very scenic. Cozy. If you’re looking for a melow ride, this is it.

Fox River Trail (IL)

Family Bike Ride

May, 2020 by hrickdourian

This was a great trail... We went as a Family, our youngest is 5 and oldest is 7. We all enjoyed it, make sure to spray deep woods off Ana you will be fine. Some flooded areas that you will have to climb around, a few minute on the rail road track won’t hurt anyone.

Great Western Trail (DuPage County)

I Like This Trail!

May, 2020 by garthliebhaber

There are less crossings than the Illinois a Prairie Path and less crowded so you can safely stretch your legs more. I also like the “wild-ness” of it, lots of blackbirds, prairie and wetlands. My only suggestions would be to go when it’s cool out and not too windy. Combined with the Prairie Path it makes a nice loop!

Wauponsee Glacial Trail

Could use some grade improvements and a lot fewer tire ruts, but overall a really good, easy trail.

May, 2020 by jebus27

Could use some grade improvements and a lot fewer tire ruts, but overall a really good, easy trail.

Great Western Trail (DuPage County)

I like it

May, 2020 by garthliebhaber

Nice faster trail with less crossings, best ridden early in the morning or during cool season. Also better done with the wind to your back! Plenty of blackbirds and other prairie wildlife.

John Husar I&M Canal Trail

Rough Ride

May, 2020 by bjohns3

Needs some TLC. This will be a nice trail once it is resurfaced and the extension completed.

Danada and Herrick Lake Regional Trail

Prairie Landscape

May, 2020 by garthliebhaber

I’m glad I rode this trail today but next time would avoid the hottest time of the day because aside from the westernmost part, much of the trail is in open sky. That said, the curves are nice and the open space. I finished on the eastern end and was happy I could ride Naperville Rd. north to Blanchard and then President Street to reconnect to the Illinois Prairie Path. So it made a nice loop.

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