Westchester Horseback Riding Trails and Maps

869 Reviews

Looking for the best Horseback Riding trails around Westchester?

Find the top rated horseback riding trails in Westchester, 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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  • Length
Activities
Length
Surfaces
Type
14 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
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

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Trails by activity

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...

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...

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...

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...

Accordion

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...

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...

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...

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....

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...

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...

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...

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,...

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...

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...

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....

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....

Accordion

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...

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...

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...

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,...

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...

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...

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...

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...

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...

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...

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,...

Accordion

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...

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...

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...

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....

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...

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...

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...

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,...

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

Hickory Creek Bikeway

Great starter trail

August, 2018 by ss10dittem

Nice scenic path covering 2 creeks and a small bridge. Connects to a longer path if wanting an extended ride. Definitely a few hills but nothing to taxing, especially with the tons of bench's they have directly next to the path you can take a break whenever you like. A bunch of shaded path makes it both beautiful and a great choice on a hotter day.

Des Plaines River Trail

Walk to Big Bend Lake

August, 2018 by stclaircarl

Started at Dam No 4 Woods and walked to Golf Rd and Big Bend Lake , saw plenty of animals deer, squirrels , chipmunks and beautiful scenery along the trail. Nice peaceful walk plenty to see , nice surface to walk on not muddy saw 1 deer by the 294 underpass and south of Oakton St saw 2 deer in the woods about 20 feet away from me, what a beautiful sight to see a doe and her fawn took pictures of this. It was a beautiful walk and I had a lot of fun.

Thorn Creek Trail

Great trail with varied views.

July, 2018 by abn2nds

Decided to do this trail instead of the Old Plank Trail. Much better than the long straight trail. Many winding turns, the loop through the Preserve at the end is a nice turn around spot. Signage could be a little better though.

Accordion

Prairie Duneland Trail

Great trail!

July, 2018 by lhuhn48837

Road the trail today and had a great experience. If part of it was once bumpy, it has been repaired. Most of the trail is new and all of it is terrific to ride. Beautiful scenery, bathrooms along the way, easy to park and get on. We rode all 10 miles and will come back again and again.

Fox River Trail (IL)

When will repairs be completed ?

July, 2018 by abraxus48

First off, this is my go-to trail and I love it. However, there are 2 areas of the trail that have been closed too long and I wonder who is responsible for making repairs.

The first is on the south side of Elgin along Raymond St where the path used to run along Poplar Creek and go under a bridge. That portion of the trail has been closed for several years now and nothing appears to be happening with regard to repairs.

Bikers are forced to proceed south on Raymond then right on Riverview Drive and go 2-3 blocks to rejoin the trail. There are no directional signs for users to follow.

The second area is near the South Elgin dam where brush and fallen branches have closed the trail making it necessary to cut across a grassy field adjacent to an industrial area in order to rejoin the trail. Again, no signs are in place to aid bikers to find their way around.

Again I ask who is responsible for repairing these areas?

Millennium Trail

My favorite so far!

July, 2018 by thundercamel

I love this trail for biking! Great forest and savanna scenery. Thankfully most of it is not parallel to roads, and none of it is old train tracks, which I find more boring. Really feels like you're moving across country under your own power.

Des Plaines River Trail

North End 5 stars,,South End not so much

July, 2018 by esobolewski01

We live near the southern section of this trail, so we have rode that portion multiple times. It is a night and day difference with the northern portion. The southern end is just not very pleasant. Trail is in poor shape, poor signage and due that section of river, the area is prone to flooding. Viaducts are usually impassable, flora is mostly invasive species, lot of trash , etc etc.

The north end however (maintained by Lake Co. as opposed to Cook Co.) is just great. Well groomed, tons of signage, usable viaducts, clean, etc. This section meanders through forest, open prairie , some farmland. The scenery is beautiful, especially mid summer with the plants in full bloom.

Highly recommend sticking to north of Cook Co. We plan on finishing the entire trail a section at a time until we hit Wisconsin!

Lincolnwood Valley Line Trail

Walking on Valley Line Trail

July, 2018 by stclaircarl

Walked the trail from Bryn Mawr to Touhy and had a excellent time. very happy to see the Touhy overpass being built and the call boxes that can summon medical help if needed are excellent to have if a person does not have a cell phone to call 911 once my bicycle is repaired I will be riding this trail from Bryn Mawr to Dempster.

Valley Line Trail

Walking on Valley Line Trail

July, 2018 by stclaircarl

Great trail to walk on once my bicycle is repaired I will be riding this trail all the way up to Skokie , nice that Sauganash Park is by the trail for use of the drinking fountain or restrooms.

Old Plank Road Trail

Review for inline skating

July, 2018 by gitahouse

The reviews are ALL about biking. This trail is sort of inline friendly but it has a lot of flotsam, sticks, debris from trees, and there are lots of repairs made with that sticky tar substance, that the skate wheels are not too good on. Some parts are pretty rough asphalt and some are fairly smooth. Bigger wheels are probably better, though they also make you faster. The street crossings are semi cut curbs with lots of bumps and broken cement to make your wheels stick, unless you're good at navigating these obstacles or good at jumping. This gets worse the further east you go on the trail. *There's a few places where the trail runs downhill (going W at Wolf Rd for one) and then spills directly into a busy street. You'd better practice your stopping skills. I think they should send a sweeper down this path at least a few times a month. I bike this trail and it's really good for that. I've skated it as well, but that was over 10 years ago when I was more confident. One bad fall with a twisted rotator cuff made me more wary since (a jogger wouldn't make way and my avoidance of her made me lose it). People walking 3 abreast and those with dogs on long leashes are also good to avoid.

Erie Lackawanna Trail

nice, but...

July, 2018 by ltlarrow

Ditto on the comments about bumpy sections. The trail could use some better signage where it deviates, and could use mile markers. Also, I suggest if you start in the north, park behind the Wendy's next to the Indiana Welcome Center along I-80. Besides the south end, that's the only restroom you will find on the trail. And watch out crossing roads...seldom will drivers stop for you.

Lincolnwood Valley Line Trail

Walked from Bryn Mawr to Touhy

July, 2018 by stclaircarl

Excellent trail to walk on, once I get my bicycle repaired I will be riding this trail Great idea to have the callboxes that way if someone needs medical help they can be taken care of.

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