Oconomowoc, WI Horseback Riding Trails and Maps

809 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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11 Results
Activities
Length
Surfaces
Type

Bugline Trail

17.42 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

Prairie Trail (IL)

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

Rock River Parkway Trail

2.4 mi
State: WI
Asphalt, Concrete

White River State Trail

19.7 mi
State: WI
Concrete, Crushed Stone, Gravel

Muskego Recreation Trail

7.5 mi
State: WI
Crushed Stone, Dirt, Gravel

Old Plank Road Trail (WI)

37.6 mi
State: WI
Asphalt

Pelishek-Tiffany Nature Trail

6 mi
State: WI
Dirt, Grass

Wild Goose State Trail

34.5 mi
State: WI
Asphalt, Crushed Stone, Dirt, Grass

CamRock Trail

2.4 mi
State: WI
Crushed Stone
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 17.42-mile...
WI 17.42 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 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 26.4 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 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 section...
WI 19.7 mi Concrete, Crushed Stone, 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 7.5 mi Crushed Stone, Dirt, Gravel
The Old Plank Road Trail parallels State Route 23—a road originally built out of wooden planks in the 1800s—from the western edge of Sheboygan to the Village of Greenbush. The trail was one of the...
WI 37.6 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
Closure Notice: The Wild Goose State Trail is currently closed between Prospect Rd. and Teal Rd. Please check with Wisconsin DNR for more current information. The Wild Goose State Trail is a...
WI 34.5 mi Asphalt, Crushed Stone, Dirt, Grass
The CamRock Trail travels 2.4 miles through its namesake CamRock Park in Cambridge, Wisconsin. CamRock Park, managed by Dane County Parks, offers a number of ammenities to trail users including...
WI 2.4 mi Crushed Stone

Recent Trail Reviews

Bugline Trail

Nice paved trail except for all the road crossings at the south end

July, 2026 by y1htak2

We started in downtown Menomonee Falls. We parked in Mill Pond Park on Roosevelt, then rode our bike over to Water Street where the trail begins. That probably wasn’t the best place to start because we had to cross the two scary intersections; Highway 175 with a crossing light and Main street on a long diagonal with no crossing light.

This is a very nice trail with wooded areas that pass through residential areas and some business areas. The northern end has some fields. On the southern end you have to stop to cross at a lot of roads all the way to and through Sussex. Luckily the car drivers are very courteous and stop to let you cross. It was nice to see kids of all ages on the trail. It’s pretty flat until you get past the Fireman’s Park soccer fields in Merton. Then you have some pretty steep hills.

Mascoutin Valley State Trail

A nice country trail in 2 segments but hard to find trailheads and parking

July, 2026 by y1htak2

Made up of 2 nice country trails with mostly decent crushed limestone surface separated into 2 parts by highway 23 which is an unsafe, busy, fast highway with a pretty wide gravel shoulder. There are no toilet facilities. Some biting flies if you stop but we didn’t get any ticks.

We first attempted to ride the Ripon to Berlin segment. In Ripon you can park slightly past the start of the trail off Locust where there is a nice parking area and pavilion. We only got about 6 miles or so before we had to stop for a very large downed tree. We could have stopped at Vines and Rushes Winery but it was a little early for us.

At the Berlin side of the trail there was a sign in a grassy area for parking across the street from where the grassy trail begins at Berlin Feed. Didn't look like that end of the trail got much use. It wasn’t worth getting tandem bike out of van to ride just a few miles so didn’t ride that part.

Then we rode our bike from Rosendale to Fond du Lac. We parked along the side of Zamzow (neighborhood) Park on Willow Creek Rd just off North St. We rode the short segment to Hwy 26 and then turned around and rode to Fond du Lac where trail ends on VVV with trail head parking.

Wild Goose State Trail

Beautiful shaded part of the trail in Fond du lac county. Four tree areas blocking path southwest of Oakfield.

July, 2026 by barb.frank0709

Beautiful shaded part of the trail in Fond du lac county. Four tree areas blocking path southwest of Oakfield.

Accordion

Lake Geneva Bike Path

Agree with other Reviews

July, 2026 by jboepple

Poorly marked. Several sections are in need of repair. Several unexpected "end of trail" dead ends. Very disappointed. Wish a safe route was created to hook up with the White River State Trail, which is only a few miles away, but to access it you need to traverse country roads posted at 55 MPH and with little to no shoulder.

Military Ridge State Trail

Rider Beware

June, 2026 by nhx9h7gjw7

Love this trail but rode today between Riley and Brigham County Park and found the trail to be in extremely rough shape on either side of Mt. Horeb. Lots of ruts, giant holes and loose sand. Slow your roll and pay attention to utility flags and sticks identifying some of the bigger holes. Stay safe!

Wild Goose State Trail

beautiful trail

June, 2026 by 47gkpg2wy5

Beautiful country trail. A lot of tree cover and not very many other people. Worth the ride.

Glacial River Trail

a lot of road riding

June, 2026 by 47gkpg2wy5

We took this trail from the Wild Goose trail but had no idea we would be on so many roads. As you got closer to Watertown, you are also on the road. We personally try to avoid roads as much as possible so we didn’t like this part. We only went to Watertown from the North so I am not sure what the rest of the trail is like. The actual bike paths are great.

Seven Waters Bike Trail

flat

June, 2026 by sterp8

I think it was a nice trail. We started out in Rochester and went north Very flat so there is constant pedaling. Good signage. No bathrooms until Meyer Park or Heg park and pray they are open.

White River State Trail

Update!

June, 2026 by b7ggzfh8h9

As of June 15th, the trail is now open between Burlington and Lyon.

White River State Trail

Between Spring Valley road trailhead and Lyon the trail was closed due to 2 bridges being washed out

May, 2026 by fredklausegger

Between Spring Valley road trailhead and Lyon the trail was closed due to 2 bridges being washed out

Muskego Recreation Trail

Beautiful trail with varying gravel conditions

May, 2026 by nkanute

great gravel cycling! Everyone complaining must be riding some skinny tires or should stick to the oak leaf- this was a very fun ride (I run 40mm semi slick tires and had no issues)

Kenosha County Bike Trail

Lots of shade and well maintained

April, 2026 by gypsycyn

A short but pleasant ride, with lots of shade, smaller wildlife, rest benches, even a couple pet stops with water dishes for the fur babies.

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