Caledonia, WI Horseback Riding Trails and Maps

658 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.

  • Relevance
  • Name
  • Length
  • Most Popular
Activities
Length
Surfaces
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

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
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

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 30,000 of trail maps
  • Share your trail photos
  • Save your own favourite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

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...

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...

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...

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...

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...

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...

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...

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...

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...

Accordion

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...

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....

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...

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...

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...

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...

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...

Accordion

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...

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....

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...

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...

Recent Trail Reviews

Hank Aaron State Trail

Riding the Tandem in Milwaukee

July, 2019 by utpaduke

Mel & I drove from Raleigh to Milwaukee to see the Braves play the Brewers for a Mon-Wed series. We brought the Tandem bike. On Mon-Tues we rode out 6.2 miles from the west trail end-point to the Three Bridges Park and back. For convenience, We parked @ the Target parking lot. Along this section, The trail is mostly flat, well-paved, and very clean. It passes behind some industrial complexes, the State Fair complex, and some residential subdivisions. The street crossings requiring more care, were few, as the major street intersections utilized trail overpasses! As baseball fans, we felt honored to ride the HANK AARON TRAIL! If I come back with my single trail bike, I would love to ride the entire trail, and also the Oak Leaf Trail which joins up right where we began our ride!

Fox River Trail (IL)

Fox River Trail

July, 2019 by farrells3

We’ve only done Oswego to Geneva so far but I’m already so impressed. Beautiful well maintained trail. While it’s a great trail for getting a workout in you’ll be torn between it and stopping to take in the amazing scenery.

Seven Waters Bike Trail

Above average trail

July, 2019 by ericevan

I recently rode this trail from south of Burlington to Wind Lake round trip. I'll be honest, I thought it would be more scenic than it was, but it didn't disappoint either. The portion through Burlington goes fast as there's plenty to see in the town, including nice views along the river. In between, there are long-winded stretches that don't excite. Think crushed limestone path, lots of sun, and nothing else. Case Eagle Park and Saller Woods were nice, but not a large segment of path either. Heading north you've got a few places to stop for amenities like Rochester, Waterford and Wind Lake, where I chose to stop. I know the trail extends up close to Franklin but I chose to turn around near Muskego Lake. This provided me with a 30+ mile round trip ride. Along the way and I can't recall where it was, is a VFW (or similar entity) that houses a tank, helicopter and a couple of jets. They're right on the path and worth stopping to admire. Cheers.

Accordion

Fox River Trail (IL)

My 'Home' trail

July, 2019 by ericevan

I've been riding the FRT from Oswego to South Elgin for over 25 yrs. And there isn't a bad part. Traveling along a scenic river while riding from town to town will please all bikers of any age. The FRT is a string of majestic sites like a huge windmill, island parks, sculptures, Riverboats, picturesque river views, a slew of bike shops, plenty of parks and places to stop. The path runs on both sides of the river and for many stretches on both. The trail itself is always in impeccable condition and varies in traffic from bikers, joggers and walkers. This is one of the best trails in Illinois, if not the best.

Eisenbahn State Trail

diesel50

July, 2019 by diesel50

Nice trail and well maintained

The trail is paved and used by many in West Bend. As you travel north, the trail is limestone and has loose top gravel that will slow your pace from hard packed limestone. A scenic and tranquil ride from Kewaskum to Eden. I've ridden it several times and will come back.

Des Plaines River Trail

Des Plaines River Trail

June, 2019 by stclaircarl6

great trail to walk on if it is not muddy have walked from Devon to Algonquin road and had no problems

Muskego Recreation Trail

Rough ride. Wish the trails would be fixed now that the new power lines are up. Might wait till next year to ride this trail again.

June, 2019 by abessa4

Rough ride. Wish the trails would be fixed now that the new power lines are up. Might wait till next year to ride this trail again.

Hank Aaron State Trail

Western section of trail is now open.

June, 2019 by brthompson

For the past few years the section of the trail has been closed while the Zoo Interchange was reconstructed. It is now open (and paved) all the way to the Oak Leaf Trail at Blue Mound and the Underwood Parkway.
A nice ride with only 2 hills.

City of Franklin Hike and Bike Trail

Tore up

May, 2019 by vulpine_77

This is all ripped up now, they are replacing the power lines. Still rideable but not relaxing

Hank Aaron State Trail

Under Construction/More

April, 2019 by dancesinggirl6

The areas around the trail especially in the three bridges park are quite bare currently.

I really wish that there were permanent "available/not locked" bathrooms along the trail itself besides at the urban ecology center and the seasonal port-o-potties during baseball season...Would be nice also if there was a light fixture on the bridge itself that is the exit of the three bridges park.

Otherwise this long trail that goes in different directions is pretty awesome. I've seen skunks and even frogs a few times last summer...

Middlefork Savanna Trail

Nature’s Haven

April, 2019 by jsenra4440

Took a early spring hike and path is wide and very easy to navigate. An occasional bench to sit, watch and reflect. Birds were everywhere. Some sightings were red headed woodpeckers, flicker woodpeckers, blue birds, blue jays, sand hill cranes, killdeer,,brown creeper, numerous red wing black birds and robins and many more birds I can’t name. Enjoyed taking the grassy trails that took us closer to water. A delightful place to visit!

Fox River Trail (IL)

Algonquin to Elgin, September 2018

October, 2018 by rdwyer416

If you start in Algonquin I suggest parking in the park at the corner of Rt. 62 and Main St. I parked near the clock tower and had to ask a passing cyclist where to catch the trail. Once on the trail, the portion from Algonquin to Elgin is one of the best marked trails I've been on. It is very well maintained and passes through historic areas and scenic beauty. There were many walkers and joggers as well as cyclists. Also, there are plenty of quality rest areas along the way.

Find Nearby City trails

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

OR

Register for free!

Join TrailLink (a non-profit) to view more than 30,000 miles of trail maps and more!

Register with Google

OR