Caledonia, WI Horseback Riding Trails and Maps

953 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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9 Results
Activities
Length
Surfaces
Type

Bugline Trail (Route of the Badger)

17.42 mi
State: WI
Asphalt

Des Plaines River Trail

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

Hebron Trail

6.7 mi
State: IL
Crushed Stone, Gravel

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

White River State Trail (Route of the Badger)

19.7 mi
State: WI
Concrete, Crushed Stone, Gravel

Pelishek-Tiffany Nature Trail

6 mi
State: WI
Dirt, Grass

Muskego Recreation Trail (Route of the Badger)

6.7 mi
State: WI
Crushed Stone, Dirt, Gravel
Trail Image Trail Name States Length Surface Rating
Overview 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...
WI 17.42 mi Asphalt
Overview 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...
IL 56.1 mi Asphalt, Crushed Stone, Dirt, Gravel
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
Overview 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...
IL 25.5 mi Asphalt
Overview 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...
IL 26.4 mi Asphalt, Crushed Stone, Dirt, Gravel
Overview 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...
WI 19.7 mi Concrete, Crushed Stone, 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
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, Gravel

Recent Trail Reviews

Oak Leaf Trail (Route of the Badger)

Great trail!

September, 2024 by nadia.rasberry01

Well maintained trail, no garbage or anything on the path! Was great for walking with a stroller there was one roughest patch we hit but that was it. Amazing views and a nice breeze from the water. Very active trail, pretty busy area.

Ozaukee Interurban Trail (Route of the Badger)

This has to be one of the top 2 or 3 bike routes in the greater Milwaukee area.

September, 2024 by zero2epiphany

I have ridden this from Brown Deer to just a bit past Port Washington and still need to do the whole thing. On the Soutern side where it starts its no different than say, Zipline or the Brown Deer connector. But once you start getting close to Cederburg, it starts to shine, with a dip in scenery when you transition through Grafton. Then the trail SHINES BRIGHT right into Port Washington. This and Bugline are probably my favorite rides in the greater Milwaukee area.

New Berlin Recreation Trail

Great for strollers!

September, 2024 by nadia.rasberry01

This trail is beautiful, it’s very smooth and works great for if you have a kiddo in a stroller! Lots of wildlife, we saw birds, bunny’s, squirrels, chipmunks, and 2 foxes!

Accordion

Ozaukee Interurban Trail (Route of the Badger)

Ok..

September, 2024 by the_masseuse

Decent enough trail.. kinda rough with all the cracks. The name of the trail wasn’t lying, very urban indeed. Not much for views and quite a bit of road crossings. Seemed like a light incline the whole time. Hardly anyone waves or smiles back. In town trail is marked well.

Robert McClory Bike Path

street crossings

September, 2024 by given.sandra

We just rode this trail yesterday. Started at the south section of the Kenosha County trail. The limestone is well maintained and we didn’t see any trash or broken glass as others stated. It’s a great path but we didn’t like the numerous crossings. Folks don’t stop even when you push the yield light button. The north part of the trail goes thru sketching areas but we felt safe. Best part was when you get to the Great Lakes Naval station as the path is paved n beautiful. I doubt we’ll redo this one but do recomend for others who don’t mind the crossings.

Glacial Drumlin State Trail (Route of the Badger)

Beautiful trail ride!

September, 2024 by tedijw

Perfect biking day in September on an awesome trail. Started in Wales and biked to Sullivan and made return trip for total of 23 miles. First portion of trail was paved and remaining portion was well-maintained crushed gravel. Highly recommend this trail and will do again.

Kenosha County Bike Trail (Route of the Badger)

nice trail

September, 2024 by given.sandra

Nice trail that is maintained well.

Eisenbahn State Trail (Route of the Badger)

Hidden Gem

August, 2024 by given.sandra

Loved this trail. Finished it on the 28th. Nicely maintained n beautiful scenery. Recommend highly.

Glacial Drumlin State Trail (Route of the Badger)

best trail

August, 2024 by given.sandra

We absolutely love this trail. Many areas are shaded. Waukesha section is totally paved. It’s a gem!

Brown Deer Recreational Trail

great connector trail

August, 2024 by given.sandra

Nicely paved short trail that connects to Ozaukee trail. Brown Deer is a great place to park.

Des Plaines River Trail

Lake County is Awesome

August, 2024 by given.sandra

We completed this trail and absolutely loved the Lake County side. It’s about 32 miles long and nice, peaceful, ride. Once you enter Cook County, it’s very rough, tough and rocky ride. Extremely uncomfortable ride. Will not do that section again but will do Lake County side.

White River State Trail (Route of the Badger)

Lots of shade along the whole trail and the scenery is nice. Also, there's not a lot of people, so it's usually a really peaceful ride.

August, 2024 by rashielx

Lots of shade along the whole trail and the scenery is nice. Also, there's not a lot of people, so it's usually a really peaceful ride.

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