Pewaukee Horseback Riding Trails and Maps

488 Reviews

Looking for the best Horseback Riding trails around Pewaukee?

Find the top rated horseback riding trails in Pewaukee, 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

15.6 mi
State: WI
Asphalt

Des Plaines River Trail

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

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

Old Plank Road Trail (WI)

17 mi
State: WI
Asphalt

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 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 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 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 17 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 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...

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...

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...

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...

Accordion

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...

Old Plank Road Trail (WI)

WI - 17 miles

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...

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...

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...

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...

Old Plank Road Trail (WI)

WI - 17 miles

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...

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...

Accordion

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...

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...

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....

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...

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...

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...

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...

Old Plank Road Trail (WI)

WI - 17 miles

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...

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

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...

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...

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...

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....

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...

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...

Recent Trail Reviews

Oak Leaf Trail

no extension to Bender park

August, 2018 by crswit

First let me start by saying the Oak Leaf trail is an excellent trail that circles Milwaukee county. I have been using this trail ever since it use to be called the '76' trail. Unfortunately, I haven't been on the south end in years. I recently decided to go south(starting at Greenfield park) with the intent to get to the newer of Milwaukee Counties parks, Bender park. When I got to Drexel at which point I would normally go straight east toward Grant Park I found I was able to continue South. Not having checked the trail map prior to my adventure I made the assumption that the ability to go further South of Drexel would somehow meander its way to Bender park. Unfortunately I was mistaken. Needless to say I managed to get to Bender park by going East on Ryan Rd./Hwy 100. I eventually got back on the Oak Leaf trail down near Grant park after heading North from Bender park through South Milwaukee on 5th Ave. Let me once again reiterate how awesome the Oak leaf trail is and how I should have checked the map prior to my excursion. As an avid biker I can only hope that at some point there will be an extension/offshoot of the Oak leaf trail that will allow bikers to safely get to that corner of Milwaukee county via trails.

Bugline Trail

beautiful...

August, 2018 by tradrrr

In town for a tri and rode the trail this morning. It’s really nice and well marked. I forgot I had ridden it once before years ago until I came across the quarry with the most beautiful blue water.

White River State Trail

Nice country trail

August, 2018 by mail4denisk

I had a very nice bike ride on the trail from Elkhorn to the west end of Burlington. Started at the well-marked parking lot just east of Elkhorn, the trail is relatively flat and hard-packed gravel. It passes through farm fields and rich tunnels of greenery. I enjoyed lots of colorful wildflowers and birds along the way. Even glimpsed a beaver that visited the trail near the White River bridge. The creeks and river are well marked, and there are plenty of benches to rest along the way. Took a little side trip off trail in Lyons and visited its veterans memorial at the flag pole, listing its local war heroes dating back to the Spanish-American War. There's a nice coffee shop in Springfield. I rested in its shady yard, but it's only open on weekends. Heading back from the Burlington trail head, I noticed the trail gradually goes uphill, or at least it seemed that way, as I completed the 24-mile round trip on a hot summer day.

Accordion

Des Plaines River Trail

Walk to Big Bend Lake

August, 2018 by stclaircarl

Started at Dam No 4 Woods and walked to Golf Rd and Big Bend Lake , saw plenty of animals deer, squirrels , chipmunks and beautiful scenery along the trail. Nice peaceful walk plenty to see , nice surface to walk on not muddy saw 1 deer by the 294 underpass and south of Oakton St saw 2 deer in the woods about 20 feet away from me, what a beautiful sight to see a doe and her fawn took pictures of this. It was a beautiful walk and I had a lot of fun.

Millennium Trail

My favorite so far!

July, 2018 by thundercamel

I love this trail for biking! Great forest and savanna scenery. Thankfully most of it is not parallel to roads, and none of it is old train tracks, which I find more boring. Really feels like you're moving across country under your own power.

Des Plaines River Trail

North End 5 stars,,South End not so much

July, 2018 by esobolewski01

We live near the southern section of this trail, so we have rode that portion multiple times. It is a night and day difference with the northern portion. The southern end is just not very pleasant. Trail is in poor shape, poor signage and due that section of river, the area is prone to flooding. Viaducts are usually impassable, flora is mostly invasive species, lot of trash , etc etc.

The north end however (maintained by Lake Co. as opposed to Cook Co.) is just great. Well groomed, tons of signage, usable viaducts, clean, etc. This section meanders through forest, open prairie , some farmland. The scenery is beautiful, especially mid summer with the plants in full bloom.

Highly recommend sticking to north of Cook Co. We plan on finishing the entire trail a section at a time until we hit Wisconsin!

Des Plaines River Trail

from Touhy Ave to Bender Road

July, 2018 by stclaircarl

Had a great time walking this section of trail saw 2 deer at Touhy and by the 294 underpass walked up into Des Plaines by Bender Road.

Oak Leaf Trail

Closed Bathrooms

July, 2018 by brittany.thompson18

Not alot of open bathrooms near The Landing stretch. Oh yes they are marked on the map but locked 95% of the time. Very nice trail otherwise. Get some permanent port a johns please!!!!

Bugline Trail

Nice trail

July, 2018 by jo turner

Nice trail. Paved. Green tunnels. Pleasant even on a hot July mid-day. Lots of busy road crossings. 99% cars stopped for crossing, but never sure about that other 1%. DH and I ride a tandem recumbent trike with a wide turn radium and many corners were not wide enough for us in one pass.

Eisenbahn State Trail

loved this trail

July, 2018 by hargreaves48

My friend and I bike the whole trail. It was hot out but had a great breeze. There are lots of bridges, great scenery, mostly gravel, but paved on the west bend end. There are bugs so spray and you’ll be fine. Fun trail. If us, 2 old ladies and do it, you can too. We are over 70!

Des Plaines River Trail

beware of the water

July, 2018 by epc.lots

Great trail full of changing landscapes, the only pity is that many times it's impossible to ride it because it's flooded.

Apart from that, a well worth trail.

Des Plaines River Trail

First ride with my son

June, 2018 by sumptonjackson29

Me and my son started just east of the Des Plaines library and we stopped just south of the airport and I must say that I absolutely love this trail. Eventually I will make that trip to gurnee. Just an absolute beautiful trail

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