Oconomowoc, WI Horseback Riding Trails and Maps

526 Reviews

Looking for the best Horseback Riding trails around Oconomowoc?

Find the top rated horseback riding trails in Oconomowoc, 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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9 Results
Activities
Length
Surfaces
Type

Bugline Trail

15.6 mi
State: WI
Asphalt

Hebron Trail

6.7 mi
State: IL
Crushed Stone, Gravel

Mascoutin Valley State Trail

21 mi
State: WI
Crushed Stone, Grass, Gravel

Muskego Recreation Trail

6.7 mi
State: WI
Crushed Stone, Dirt

Prairie Trail (IL)

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

Rock River Parkway Trail

2.4 mi
State: WI
Asphalt, Concrete

White River State Trail

19 mi
State: WI
Concrete, Crushed Stone, Gravel

Wild Goose State Trail

34.4 mi
State: WI
Asphalt, Crushed Stone, Dirt, Grass
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 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 Mascoutin Valley State Trail is divided into two segments along a former corridor of the Chicago and North Western Railway. The eastern section runs 10 miles between Fond du Lac and Rosendale. The...
WI 21 mi Crushed Stone, Grass, Gravel
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 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 Rock River Parkway Trail in Janesville runs between Rockport Park and S. Jackson Street bridge on the north side of the river. Here, at the trail's eastern terminus, you can easily link to Spring...
WI 2.4 mi Asphalt, Concrete
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
The Wild Goose State Trail is a premier rail-trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. If you are looking for a peaceful and beautiful place to visit, this trail has it...
WI 34.4 mi Asphalt, Crushed Stone, Dirt, Grass

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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...

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...

Wild Goose State Trail

WI - 34.4 miles

The Wild Goose State Trail is a premier rail-trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. If you are looking for a peaceful and beautiful place to visit, this trail has it...

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

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...

Rock River Parkway Trail

WI - 2.4 miles

The Rock River Parkway Trail in Janesville runs between Rockport Park and S. Jackson Street bridge on the north side of the river. Here, at the trail's eastern terminus, you can easily link to Spring...

Rock River Parkway Trail

WI - 2.4 miles

The Rock River Parkway Trail in Janesville runs between Rockport Park and S. Jackson Street bridge on the north side of the river. Here, at the trail's eastern terminus, you can easily link to Spring...

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....

Mascoutin Valley State Trail

WI - 21 miles

The Mascoutin Valley State Trail is divided into two segments along a former corridor of the Chicago and North Western Railway. The eastern section runs 10 miles between Fond du Lac and Rosendale. The...

Accordion

Wild Goose State Trail

WI - 34.4 miles

The Wild Goose State Trail is a premier rail-trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. If you are looking for a peaceful and beautiful place to visit, this trail has it...

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...

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...

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...

Rock River Parkway Trail

WI - 2.4 miles

The Rock River Parkway Trail in Janesville runs between Rockport Park and S. Jackson Street bridge on the north side of the river. Here, at the trail's eastern terminus, you can easily link to Spring...

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...

Wild Goose State Trail

WI - 34.4 miles

The Wild Goose State Trail is a premier rail-trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. If you are looking for a peaceful and beautiful place to visit, this trail has it...

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...

Accordion

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...

Mascoutin Valley State Trail

WI - 21 miles

The Mascoutin Valley State Trail is divided into two segments along a former corridor of the Chicago and North Western Railway. The eastern section runs 10 miles between Fond du Lac and Rosendale. The...

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...

Recent Trail Reviews

Bugline Trail

The Bugline is a sweet little trail NE of Milwaukee

July, 2020 by matthewge

Here a great R2T for those in SE Wisconsin! The Bugline Trail, just NW of Milwaukee. Oddly named, but a sweet trail. I started in Merton, rode to Menomonee Falls and back. 26 miles round trip, all paved. A great mix of woods, open areas, and some developed areas. There are several little towns along the trail (Merton, Sussex, Lannon, Menomonee Falls) where you can pick up snacks if needed.

As it passes thru Lannon, WI -- which provided the limestone that built much of Milwaukee -- you will see lots of quarry lakes, including one that is just shockingly blue!

If you are in the area, give it a try!

KR Trail

great path!

July, 2020 by savannahwillkomm

I take this path from old spring street in mount pleasant (pike river trail) through pets park to the Kenosha Racine trail. The paved paths through the fields from hwy 11- KR are beautiful! The paths that run parallel to Green Bay road is very nice. I love this whole trail!

Capital City State Trail

July 4, 2020 ride

July, 2020 by carmenmpalladino

Beautiful ride felt real safe after riding in south Florida. Just enough elevation change for fun and not work. Enjoy

Accordion

Wild Goose State Trail

underwhelming

June, 2020 by ucrubr

Road the entire trail from fox du lac to Juneau. Plus a side 3 or so miles at the Horicon. It was so much the same. Not much changed all the way. Few people on it so it was a bit boring. Not much to visit along the way and Juneau didn’t have much either. I didn’t hate it but I wouldn’t do it again. Lots of bumps and the trail was ok otherwise. Just meh.

Wild Goose State Trail

Ruts

June, 2020 by alanelle

There are a few deep ruts caused by equipment used to push over dead trees that need repairs. Some are difficult to see until you are on top of them.

Glacial Drumlin State Trail

beautiful trail...

June, 2020 by tradrrr

A gravel/crushed limestone trail with some shade in parts. I rode it from London east 20 miles today after it poured yesterday and the trail was bone dry. I’d recommend having 28s on your bike as smaller tires can work but it’d be a little more difficult. There was a small stretch on streets but it was well marked and little traffic. I loved the bridges over the water and the small tunnel you pass through (keep your hands on the bars as it’s bumpy in there). There was a smallOverall a great trail.

Long Prairie Trail

Nice trail, not crowded at all

June, 2020 by wphan

Did the entire trail plus stone bridge trail and back with the family(spouse, teenage and pre teen boy). Both trails were nice and not crowded at all. Great trail for family with young kids (hardly any super fast cyclists). Trail get bumpy a bit outside poplar grove. Good mixture of shade and sun.strongly suggest continue on to stone bridge trail.
Had burrito from the Mexican restaurant at the gazebo by the trail in poplar grove.( no dine in during pandemic) supernice staff even brought out food out to gazebo! Will definitely come back.

Glacial River Trail

I've upped my review to 5 stars

June, 2020 by wilsonae

This has easily become my favorite frequent trail ride in the Rock County area. I've now completed the trail from Janesville to Johnson Creek and it is gorgeous and not busy and I don't even notice the traffic anymore. Excellent trail for road bikes. Quick tip: my favorite place to get on the trial is north of Janesville near the Janesville Animal Medical Center at 5021 N Wright Rd in Milton. You skip the road ride on HWY Y, which is the only section I don't care for. And then it is just miles and miles of well maintained trail and beautiful country scenery. Enjoy!

Badger State Trail

Great Trail

June, 2020 by evawysocki1993

This was a easy to ride trail .

Capital City State Trail

Went 6/19/20. Enjoyed the ride a lot. I prefer the country area towards fitchburg, but it was nice to ride downtown as well. If you can only do one ride while in the Madison area, I think this one is best.

June, 2020 by duleysabrinal

Went 6/19/20. Enjoyed the ride a lot. I prefer the country area towards fitchburg, but it was nice to ride downtown as well. If you can only do one ride while in the Madison area, I think this one is best.

Pike River Pathway

Couldn't get too far because of construction projects ¿¿

June, 2020 by draeg002

Couldn't get too far because of construction projects ¿¿

White River State Trail

definition of “scenery”

June, 2020 by hosmaneke63

The natural features of a landscape. So the reviewer who didn’t see scenery apparently walked trail with eyes closed¿¿

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