Greendale, WI Horseback Riding Trails and Maps

563 Reviews

Looking for the best Horseback Riding trails around Greendale?

Find the top rated horseback riding trails in Greendale, 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
9 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

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

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 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
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

Now, More Than Ever, Trails Matter!

During COVID-19, trails are being counted on as places where people can find solace and respite and we need your support to keep trails open and provide these critical FREE resources! Please continue to practice physical distancing and check the status of your trail before heading out!

Trails by activity

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...

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...

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...

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

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...

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...

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...

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...

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...

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...

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...

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....

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...

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...

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...

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....

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...

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...

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...

Recent Trail Reviews

Lake to Lake Bike Trail (WI)

would do it again!

August, 2020 by jstelzel

Left from Long Lake. Perfect for what I was looking for. Varied scenery, lots of gorgeous meadows, some forest, then swamp-like lands as you get closer to Mauthe Lake. Milder hills compared to what you’d find road biking in the area. Some shade (we left around 10:30am) but depending on time of day and position of sun you could have more shade. I didn’t need bug spray but recommend bringing just incase. Trail wasn’t busy at all. Very enjoyable ride.

Sheboygan Interurban Trail

Nice ride!

July, 2020 by emmettbrown

We rode from Belgium to Oostburg. I didn't realize that the Sheboygan Interurban was all paved. Even though I read the trail description I was still expecting gravel when we crossed Hwy. K. The trail seems well maintained and is in good condition. This section of the trail from Hwy K to Oostburg is mostly rural and follows a railroad track. A really beautiful ride. It has a suburban feel when you go through Cedar Grove. There is one road you have to take through an industrial section of Cedar Grove. On the north side of Cedar Grove at Hwy 32 & Commerce St. is a nice trail head with tables and shade and that also has a clean porta-pottie.

When you reach Oostburg the dedicated trail ends and you ride the streets. The first road north through Oostburg is a quiet residential street and it takes you to the trail head at the Oostburg train depot. There are really clean bathrooms inside and tables too. No tables outside but across the tracks to the west is Kups Coffee and Ice Cream. This is where we turned to head back to Belgium.

Lake to Lake Bike Trail (WI)

Very beautiful quick ride. Mauthe lake was flooded so it started out a very feet soaking ride... but it makes an experience!

July, 2020 by kellyprice

Very beautiful quick ride. Mauthe lake was flooded so it started out a very feet soaking ride... but it makes an experience!

Accordion

Eisenbahn State Trail

Enjoy the Ride!

July, 2020 by lbbike

I rode this trail in its entirety a few days ago. The portion through West Bend is paved, but the remainder is crushed limestone. A few portions of the trail have some plant growth, but it did not interfere with my ride. Only one small area on the gravel portion felt loose; the remainder of the trail was fine. I would recommend to plan your trip with needed supplies (sunblock, hydration, food, cell phone, and bike repair gear) as some portions of the trail are quite isolated for many miles. Overall, I did enjoy my ride and will likely be back!

Kenosha Pike Bike Trail

Lived in Kenosha for 3 years and would go on this trail weekly. It's incredible on the lake

July, 2020 by sl.johnson

Lived in Kenosha for 3 years and would go on this trail weekly. It's incredible on the lake

Sheboygan Interurban Trail

Nice Route

July, 2020 by jlmueller

Started from Kohler-Andrae SP. Not a fan of on road biking, but nice quiet roads. Nice little coffee ice cream shop “Kups” in Oostburg. Next door at the Oostburg red building are public restrooms. Paved bike trail from Oostburg south.

Moraine Hills State Park Trail

3 short loops each abt 3 to 4 miles long. Short rolling hills. Adulta will be fine, children in training wheels or bike without gears moght be a challenge. Dam area have canoe rental.

July, 2020 by wphan

3 short loops each abt 3 to 4 miles long. Short rolling hills. Adulta will be fine, children in training wheels or bike without gears moght be a challenge. Dam area have canoe rental.

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!

Des Plaines River Trail

Awesome trail. I took my fat tire bike for a 40 mile bike ride. This is great for dogs too since there's the des plaines river. Plenty of shade

July, 2020 by sillysilvia03

Awesome trail. I took my fat tire bike for a 40 mile bike ride. This is great for dogs too since there's the des plaines river. Plenty of shade

Moraine Hills State Park Trail

Went last weekend and enjoyed it. Tons of hills. One time I had to walk the bike up the hill. Other times had to drop 4-5 gears very quickly to get up the hill. Definitely want to go back in the fall.Beautiful view by the damn.

July, 2020 by heidiwagner1036

Went last weekend and enjoyed it. Tons of hills. One time I had to walk the bike up the hill. Other times had to drop 4-5 gears very quickly to get up the hill. Definitely want to go back in the fall.Beautiful view by the damn.

Des Plaines River Trail

captain Daniel Wright Woods Green Trail

July, 2020 by kllyprkns

This magnificent water view is located at Captain Daniel Wright Woods Green Trail.

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!

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

Log in with Apple

OR

Register for free!

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

Register with Google

Register with Apple

OR