Caledonia, WI Horseback Riding Trails and Maps

802 Reviews

Looking for the best Horseback Riding trails around Caledonia?

Find the top rated horseback riding trails in Caledonia, 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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Type
10 Results
Activities
Length
Surfaces
Type

Bugline Trail

15.6 mi
State: WI
Asphalt

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

Hebron Trail

6.7 mi
State: IL
Crushed Stone, Gravel

Millennium Trail

30.7 mi
State: IL
Asphalt, Concrete, Crushed Stone

Muskego Recreation Trail

6.7 mi
State: WI
Crushed Stone, Dirt

North Branch Trail

21.3 mi
State: IL
Asphalt

Pelishek-Tiffany Nature Trail

6 mi
State: WI
Dirt, Grass

Prairie Trail (IL)

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

White River State Trail

19 mi
State: WI
Concrete, Crushed Stone, Gravel
Trail Image Trail Name States Length Surface Rating
Broad blue skies strung with white cloud wisps; gem-green fields harboring cattails and butterflies; canopied glens giving way to cavernous quarries. It's all part of the ride on the Bugline...
WI 15.6 mi Asphalt
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 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 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 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 6.7 mi Crushed Stone, Dirt
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 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
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 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!

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Trails by activity

Muskego Recreation Trail

WI - 6.7 miles

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...

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...

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...

Accordion

Bugline Trail

WI - 15.6 miles

Broad blue skies strung with white cloud wisps; gem-green fields harboring cattails and butterflies; canopied glens giving way to cavernous quarries. It's all part of the ride on the Bugline...

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...

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...

Pelishek-Tiffany Nature Trail

WI - 6 miles

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...

Bugline Trail

WI - 15.6 miles

Broad blue skies strung with white cloud wisps; gem-green fields harboring cattails and butterflies; canopied glens giving way to cavernous quarries. It's all part of the ride on the Bugline...

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...

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...

Accordion

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...

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...

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...

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...

Muskego Recreation Trail

WI - 6.7 miles

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...

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....

Pelishek-Tiffany Nature Trail

WI - 6 miles

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...

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....

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...

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...

Muskego Recreation Trail

WI - 6.7 miles

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...

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...

Bugline Trail

WI - 15.6 miles

Broad blue skies strung with white cloud wisps; gem-green fields harboring cattails and butterflies; canopied glens giving way to cavernous quarries. It's all part of the ride on the Bugline...

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...

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...

Recent Trail Reviews

Glacial Drumlin State Trail

Lake Mills to Deerfield

September, 2021 by juliecat320

Beautiful trail between Lake Mills and Deerfield. Ice cream in Deerfield! No ruts - hard packed crushed limestone. I rode my road bike with out problem. Just wish they had ice

Seven Waters Bike Trail

Nice trail for a day ride

September, 2021 by stvatandem

We started at the Congress St Trailhead in Burlington and rode north to where the trail crosses Heg Park Rd. and turned around (needed to get back by lunchtime). The trail is primarily dirt, which was fine for our gravel tandem. While the trail crosses RT-36 (no signals, just a painted crosswalk), the traffic was light enough for us to get by. The median is wide enough to safely stop in if traffic is busy. The turn from the parking area at Saller Woods is a bit sandy and can lead to wipe-outs. It really needs to be wider and less sharply curved. The section of the trail from N Browns Lake Dr through Case Eagle Park out to Buck Rd (in Waterford) is paved and is a delight to ride on. North of Beck Dr (RT-20) it's back to dirt. Overall a nice ride for the morning.

Beerline Trail

Good Ride but short

September, 2021 by dpoquette

I rode the entire trail. It was well maintained, labeled and fun to ride. At Capitol drive you can still see remnants of when it used to be a railroad yard to store the rollingstock for the beer industry. There is a lot of really nice art work along the trail and best of all, you can end the ride at Lakefront Brewery for a cold beer!!

My only gripe is that there are a couple of spots in which you have to ride the road for a block or two because companies have purchased the rights along the original railroad corridor.

I'm really looking forward to the expansion going north.

Accordion

Long Prairie Trail

Nice ride

September, 2021 by chirx66

I rode the entire length ( except for The Stone bridge Trail Portion at the end). I agree with other riders that the asphalt is bumpy and repairs are needed in some sections. However, the trail is flat, tree covered and pretty much an easy ride. The trail head in Capron ( at least I think that’s Capron) has parking, facilities, and a picnic table which was nice. I would recommend everyone to ride this trailleast once

Glacial Drumlin State Trail

Ok but not a lot of features

September, 2021 by gmeister50

I started at the trail head in Cottage Grove. Paid my $5 and took off east. The path is mostly crushed lime stone and nice riding. It has slight grades but no hills. The trail is mostly straight and flat which is why I say it lacks features. Yes I know it is a converted train tracks. Lots of farms and fields with flowers. (features?) Also tree lined. It goes by many small towns along the way but they looked deserted. Didn't see many people.
I think riding the IPP and Fox River trail is better.

Palatine Trail

Nice trail with minor stops in between !!

August, 2021 by rajbms

I was looking for parking on Dundee rd to get into this trail, then realized I had to park in the Deer Grove trail and then cross Dundee and get into the trail. It’s was really nice and smooth ride until Hicks rd. After that there were multiple minor stops. But overall it was good to ride this trail. Really liked the atmosphere and the clean and well maintained path. Overall good experience!!!

Deer Grove Trail

Good not so crowded trail.

August, 2021 by rajbms

Explored the east side of this trail and was really good and well maintained. Good for road bikes as well. West side looked somewhat deserted and the roads to parking was not that great. East side is really good.

North Branch Trail

great loop trail

August, 2021 by ielpmike

It’s always nice to be able to go in a loop rather than a straight line and back. This is a really nice trail with a lot of variety of scenery and good curves. There are places where it’s really noisy because of the proximity to major highways and there are a few busy intersections to cross. The trail is in good shape but is getting close to needing repair. Overall this is a great trail and I would give it a 4 of 5.

Glacial River Trail

north branch Glacial River Trail

August, 2021 by mem9622

We absolutely loved this trail. We started near the airport in Watertown Wisconsin and took the back roads all the way to the end of the marked trail. There’s a small 2 mile segment that’s a long state route 16 but it’s a dedicated trail on the side of that road. Loud traffic but just a small section so not that bad of a deal. Everything else is beautiful country roads very little traffic absolutely wonderful rolling Hhills and farmland. It took us three hours round-trip very leisurely pace of 9 mph Be sure to eat at the Main Street diner in Watertown

Green Bay Trail

Unsafe In Certain Spots

August, 2021 by dlarsen2468

I was in the Glencoe portion of the Green Bay Trail today and witnessed a bicyclist get hit by a car. Park Avenue is a blindspot for both bicyclists and motorists. Thank you for your consideration.

Oak Leaf Trail

Popped My Tire

July, 2021 by jlm3junk

The Menominee Parkway section is horrible! So many potholes! I popped my tire and had to get an Uber back. My first ever experience with an Uber, which was much better than my bicycling experience!

Robert McClory Bike Path

Not terrible

July, 2021 by mrsmiley625

Pros: fast way to get north-south or vice versa, mostly clean gravel.
Cons:Many streets to cross, if you don't keep your head on a swivel and you stop, you have a great chance of being mugged.

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