Pleasant Prairie Trails and Maps

1159 Reviews



Looking for the best trails around Pleasant Prairie?

Explore the best rated trails in Pleasant Prairie, WI, whether you're looking for an easy walking trail or a bike trail like the New Berlin Recreation Trail and Seven Waters Bike Trail (Route of the Badger) . With more than 91 trails covering 963 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Recent Trail Reviews

Busse Woods Trail

Busse Forest Nature Preserve

November, 2023 by thejake91739

Busse Forest Nature Preserve is a slice of tranquility completely surrounded by the chaos of highways and the hectic, hurry up conditions of suburbia. It's like a mini Central Park, but in the burbs of Chicago. If I was fortunate to have something like this near my home in my metropolis of southern California I'd be hiking, biking, or fishing it every day!

Since I as staying at the Hampton Inn in Schaumberg, I simply rode my bike down the Schaumberg Bikeway alongside Woodfield Road for about a half mile to access the park.

It was shortly after sunrise on a chilly weekday morning in early October as I entered the serenity of the preserve and its forests, lakes, and large grassy areas. I was joined by dog walkers, joggers, fishermen, bicyclists, a rollerblader, and hundreds of geese.

The treelined paths were carpeted with golden leaves, and many large flocks of geese called many of the grassy areas home. I was fortunate enough to see and hear a massive bull elk making its wailing, bugle-like call in an attempt to entice two cows he was near to get cozy with him.

All in all, Busse Woods Trail is a delightful system of curvy trails, dense woods, large swaths of lawn, and beautiful lakes. What a precious gem for the communities of the burbs and this lucky visitor from SoCal!

Oak Leaf Trail (Route of the Badger)

South Shore Line

November, 2023 by thejake91739

On a perfect weekday morning in early October I experienced by bicycle the South Shore portion of the Oak Leaf Trail.
I parked in the Grant Park Beach parking lot in South Milwaukee and headed north to Cupertino Park and then back, a distance of about twelve miles. Even though it was such a short ride it took me over two hours since I had to frequently stop for the awesome photo ops. The views of the lake and the Milwaukee skyline are sensational!
The trail is obviously beloved by the community. Not only were there plenty of other bicyclists, but there were a tremendous amount of friendly pedestrians walking their dogs or getting their steps in, especially in Bay View Park.
The South Shore portion of the trail has so much to offer: woods, tree lined streets with charming homes, wildflowers, squirrels, geese, shoreline, lots of curves, five parks, yachts, and plenty of benches to take in the marvelous views of Lake Michigan and the downtown skyline. Besides the lake views, I especially enjoyed the curvy trail covered in golden leaves through the woods of Grant Park.

TWO WORDS OF WARNING:
1) There are hills.
2) There are cracked and uplifted portions of trail through the woods of Grant Park due to tree roots. They will effectively work like speed bumps and slow you down a bit.

However, all in all, this is an enjoyable ride and certainly worthy of your time and five stars!

Duck Lake Nature Area Trail

Easy walk on a grassy former railroad bed

October, 2023 by markwboettcher

This trail was actually a former C&NW railway that served Lake Geneva and terminated in Williams Bay. Service to Williams Bay started in 1888 and ended in 1965. Service to Lake Geneva ended in 1975. Thanks to Maxine Thoorsell for starting the conversion of turning this former railway into a nature trail. It is an easy grass covered walk and the trail is 1.7 miles in length. You can also access the trail at the boat launch to the west...behind the barn. A separate trail that is part of this former railway extends from Williams Bay Northeast up to Hwy 50 in the Kishwaukeetoe Conservancy

Accordion

Great Western Trail (IL)

it’s fun

September, 2023 by charliebearisgoat

It is a great trail and super fun to bike on

Bugline Trail (Route of the Badger)

Excellent trail ride

September, 2023 by jcook1950_tl

trail is in perfect condition and while there were a fair number of users, it was never crowded or congested on this saturday morning. It was a joy to ride roundtrip from menomonee falls to north lake. The only steep hill is in merton just east of dorn road. The small towns of sussex and lannon have some taverns that look interesting. Menomonee park above the north part of the trail just west of lannon road is worth a visit.

Deer Grove Trail

not a fan

September, 2023 by 97ca5crqis

Once a great hiking preserve no not so much. It is evident that funding just isn’t there for a quality site like other county trails. They still have a chain link fence blocking off an area damaged years ago which looks like an excuse to no maintain and save money. As it’s been under repair for a good 10 years. Deer grove was my backyard growing up and it was an amazing preserve it’s sad to say that it is no more

Glacial Drumlin State Trail (Route of the Badger)

awesome trail

September, 2023 by k9htwmcdmg

One of the best trails in Milwaukee area. Very scenic , beautifully paved . Stop in Dousman at Bicycle Doctor store. Great staff and a lot to look at !!

Oak Leaf Trail (Route of the Badger)

Great trail for walk surface and natural sites.

September, 2023 by lisa.radomski4

Great trail for walk surface and natural sites.

North Central DuPage Regional Trail

Beware- Not 100% Asphalt

September, 2023 by desibianca

Misleading description- was anticipating an entire asphalt ride - instead found sections to be gravel. ¿

Long Prairie Trail

Nice area, but only part of trail is rideable

August, 2023 by sarahccaltvedt

After reading other recent reviews, we first rode the Stone Bridge Trail from Roland Olson Forest Preserve to Rockton and then headed back east to the Long Prairie Trail. Once we were on the Long Prairie, the surface changed to asphalt and was reasonably ok - some big bumps and cracks were marked - until we got to Caledonia. After that the surface got worse, and we turned around when we'd gone a mile or so farther. It was a nice ride with plenty of shade, and we managed to get in about 25 miles total. Still, it's a real shame that we can't ride from the east end of the trail anymore.

North Branch Trail

15 mph bike speed limit is like "No dunking" signs at a basketball court.

August, 2023 by xegroeg_tl

15 mph bike speed limit is like "No dunking" signs at a basketball court.

Chicago Lakefront Trail

If you have time for this trail then this is a must do, NOT for kids

August, 2023 by kimlogan

We love this trail. We live in the western suburbs of Chicago so this is a trail that we do often. If you live in the area or will be traveling through, it is best to find a parking spot for your car and then get going on your bike. You can do off street parking in Chicago near the lake which is pay by hour or you can park in the numerous parking garages in the area. We get our parking spots for a major discount through spot hero. When we do this trail we like to start at the Maggie Daley park so we get a spot in one of the parking garages right there.
We start at the Maggie Daley lot near the ice skating circle and head north. There are countless beaches, restaurants, food trucks, etc. on this trail. We like to stop at the Lincoln Park Zoo because it is a beautiful free zoo. We walk our bikes through the zoo with no problem or issues.
This trail is a VERY FAST trail for good bike riders. There are TONS of people that are walking, biking, roller blading, and running on this divided trail. There are lanes that are clearly marked for bike riders but that doesn't mean that people follow the signs and the rules. If you decide to do this trail on a weekend plan for there to be a ton of people. I would not suggest that children younger than pre-teen ride individually on this trail. I would worry about children riding into the path of very fast riders and I worry about other people getting irritated with children that may fall or stop unexpectedly on this trail.
The sites that you will see on this trail are simply amazing! You can do this trail over and over again and stop at different places each time. We ride all the way to the end on the north side of town. We also go south to about the 31st beach. This takes you behind Soldier Field and the Shedd Aquarium which is a neat vantage point. We could ride this trail every weekend if we could!

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