South Milwaukee, WI Horseback Riding Trails and Maps

584 Reviews

Looking for the best Horseback Riding trails around South Milwaukee?

Find the top rated horseback riding trails in South Milwaukee, 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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7 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
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 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

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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...

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...

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...

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

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...

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....

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...

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...

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...

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...

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...

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...

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...

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....

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

Glacial Drumlin State Trail

Lake Mills to Deerfield

September, 2021 by juliecat320

Beautiful trail between Lake Mills and Deerfield. Ice cream in Deerfield! No ruts - hard packed crushed limestone. I rode my road bike with out problem. Just wish they had ice

Seven Waters Bike Trail

Nice trail for a day ride

September, 2021 by stvatandem

We started at the Congress St Trailhead in Burlington and rode north to where the trail crosses Heg Park Rd. and turned around (needed to get back by lunchtime). The trail is primarily dirt, which was fine for our gravel tandem. While the trail crosses RT-36 (no signals, just a painted crosswalk), the traffic was light enough for us to get by. The median is wide enough to safely stop in if traffic is busy. The turn from the parking area at Saller Woods is a bit sandy and can lead to wipe-outs. It really needs to be wider and less sharply curved. The section of the trail from N Browns Lake Dr through Case Eagle Park out to Buck Rd (in Waterford) is paved and is a delight to ride on. North of Beck Dr (RT-20) it's back to dirt. Overall a nice ride for the morning.

Beerline Trail

Good Ride but short

September, 2021 by dpoquette

I rode the entire trail. It was well maintained, labeled and fun to ride. At Capitol drive you can still see remnants of when it used to be a railroad yard to store the rollingstock for the beer industry. There is a lot of really nice art work along the trail and best of all, you can end the ride at Lakefront Brewery for a cold beer!!

My only gripe is that there are a couple of spots in which you have to ride the road for a block or two because companies have purchased the rights along the original railroad corridor.

I'm really looking forward to the expansion going north.

Accordion

Glacial Drumlin State Trail

Ok but not a lot of features

September, 2021 by gmeister50

I started at the trail head in Cottage Grove. Paid my $5 and took off east. The path is mostly crushed lime stone and nice riding. It has slight grades but no hills. The trail is mostly straight and flat which is why I say it lacks features. Yes I know it is a converted train tracks. Lots of farms and fields with flowers. (features?) Also tree lined. It goes by many small towns along the way but they looked deserted. Didn't see many people.
I think riding the IPP and Fox River trail is better.

Glacial River Trail

north branch Glacial River Trail

August, 2021 by mem9622

We absolutely loved this trail. We started near the airport in Watertown Wisconsin and took the back roads all the way to the end of the marked trail. There’s a small 2 mile segment that’s a long state route 16 but it’s a dedicated trail on the side of that road. Loud traffic but just a small section so not that bad of a deal. Everything else is beautiful country roads very little traffic absolutely wonderful rolling Hhills and farmland. It took us three hours round-trip very leisurely pace of 9 mph Be sure to eat at the Main Street diner in Watertown

Oak Leaf Trail

Popped My Tire

July, 2021 by jlm3junk

The Menominee Parkway section is horrible! So many potholes! I popped my tire and had to get an Uber back. My first ever experience with an Uber, which was much better than my bicycling experience!

Robert McClory Bike Path

Not terrible

July, 2021 by mrsmiley625

Pros: fast way to get north-south or vice versa, mostly clean gravel.
Cons:Many streets to cross, if you don't keep your head on a swivel and you stop, you have a great chance of being mugged.

Eisenbahn State Trail

pretty good

July, 2021 by thomas.m.durbin

good for walking, great for biking.

Sheboygan Interurban Trail

Ozaukee County to Oostburg

July, 2021 by drprovanch

This trail is very scenic as we biked north from the Ozaukee trail. We immediately could tell the difference as this trail had a more wooded or nature feel. We stopped and turned back at the trail’s end just short of Oostburg rather than following the quiet roads the short distance into the village. We wish the trail continued further into Sheboygan County without the reliance on county highways. It’s a great start!

Ozaukee Interurban Trail

Port Washington north

July, 2021 by drprovanch

We did the northern leg the second day, parking at the DOT park & ride lot at the I43 northern exit. The scenery is mostly farmland with flat terrain. There are areas with potholes which may be marked with painted circles. It is a great exercise trail as the lack of curves and people walking the trail allowed us to bike faster than normal. We continued further on the Sheboygan County trail at the north end before returning to Port Washington.

Ozaukee Interurban Trail

Mequon to Port Washington

July, 2021 by drprovanch

This is a very nice trail, well maintained and well marked when you’re biking quiet streets in the various communities. We stopped in Port Washington at a lakeside park for a break before returning to Mequon.

Robert McClory Bike Path

As we expected

July, 2021 by rastro1

Two of us rode the McClory southbound on July 2, 2021. We experienced few of the negatives described in other reviewers, especially the ones from years ago. Near the northern extreme of the trail, we experienced two spots with a little broken glass, but literally a couple of feet each and they were past. There were some gritty-looking areas surrounding the trail, mostly in Waukegan, but no people or areas anywhere that felt truly dangerous. The trail crosses a lot of streets and that slowed us down, especially since we had been riding several hours. The path was well kept throughout; it was easy to ride and we never had to reduce speed because of the surface. It's also not excessively dusty; no need to wipe down our bikes at the end of the day. We still prefer paved trails, but there's no doubt: combining this trail with the southern Kenosha County trail is an easy way to get from Wisconsin toward Chicago. The paved part, from about Waukegan through Highland Park, is a little faster and almost entirely flat. At Lake Cook Road near the Braeside Metra station, it connects with the Green Bay Trail to continue toward the city.

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