Looking for the best trails around Greendale?

Explore the best rated trails in Greendale, WI. Whether you're looking for an easy walking trail or a bike trail like the New Berlin Recreation Trail and Brown Deer Recreational Trail. With more than 59 trails covering 759 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

Middlefork Savanna Trail

Beautiful Prairie Trail

November, 2022 by erossen22

A great place for walkers, hikers, bikers, and families. It’s been wonderfully restored and brings nice surprises during each season.

Lake to Lake Bike Trail (WI)

A very well maintained Trail with services and many parking lots. We experienced a lot of foot and bike traffic especially as we got close to the campgrounds.

October, 2022 by hardenmedia

A very well maintained Trail with services and many parking lots. We experienced a lot of foot and bike traffic especially as we got close to the campgrounds.

Glacial Drumlin State Trail

East to West starting in Glendale and ending in Madison

October, 2022 by martinaxe

I started out my ride from my home about 9 miles north of downtown Milwaukee where I caught "the Hank" and made my way west to the Glacial Drumlin Trail. I started out at 3:00 am, so it didn't really get light out until I got to about Wales. After that, I was on non-paved trail (my personal fav) for the rest of the ride to Madison. The trail is really very nice and mostly flat with a lot of varying landscapes. Since it's October, there were a ton of migrating birds and pretty good fall colors all along the trail, and I didn't see another human riding until I was about 5 hours into my trip near Lake Mills. The only thing keeping me from giving this trail 5 stars are the bridges, which are mostly bad. They do have a rubber strip running down the middle of them which helps, but they are still mostly bouncy and you have to deal with a 3-6" rise at the start of each of them. The west end of the trail was closed near Cottage Grove, and I had to take a detour on streets, which was fine. This is a highly recommended ride, especially during fall.

Accordion

Hebron Trail

Nice trail for getting in a quick bike ride

October, 2022 by ktgranzow1

I had ridden the northern end of the Prairie trail & saw the sign forg the Hebron trail so decided one day to check it out. Rode from the Prairie Trail junction to the “trail end” at Lange Road & back again. About an hour round trip but that included stopping to take photos. It’s a well groomed trail, plenty wide for comfortable passing of others. West of Keystone Road crossing is pretty much straight & flat but scenery still varies.

Des Plaines River Trail

south end not great

September, 2022 by william58

I started from the south entry point and only made it a few miles in before deciding to just take the roads back south. It hadn't rained for a few days and the bridge underpasses were still full of pooled water and soft mud. I don't even know if I'd ride through them on a mountain bike unless I was really looking to get nasty.

Oak Leaf Trail

Extension to Bender Park Open but not yet ready for Use

September, 2022 by buehler868

The Milwaukee County Parks, Oak Leaf Trail webpage says the extension of the South Shore Line segment is open to Bender Park. It is not yet show on the TrailLink map. On my September 2022 trip up to the Oak Leaf Trail, to do the original South Shore Line and the Oak Creek Line, I decided to see what the new extension was like. Yes, it is open with routing signs in place and a creek bridge constructed. But the surface is made up of 1-inch sized crushed stone which is typically used as a base layer under asphalt pavement. Even though I have a gravel bike, from Drexel Ave I only made it down to Pennsylvania Ave and gave up the going further. It’s just too rough. I made the trip back using highways. I searched on the internet, and it seems that the funding grants describe a 2023 completion. I hope what is the case is the asphalt paving will be done in 2023.

Oak Leaf Trail

Riding the Southeast Quadrant

September, 2022 by buehler868

On my third trip up to the Oak Leaf Trail I did what I call the Southeast Quadrant. I parked at Greenlawn Park and did the trail and spurs down to the Racine County line and up to Cupertino Park near the Lake Michigan Ferry. What I liked about this trip was the variety in the trail. Segments consisted of rails to trails (with powerlines), trail in parks, separate trails on arterial streets, the parkway roads, and rural highways. The long, southerly segment in the forest on the bluffs along Lake Michigan was the prettiest segment of my three trips on the Oak Leaf Trail. The north segment along Lake Michigan was closer to the water and gave a nice view of downtown Milwaukee.
One concern is the trail is being extended to Bender Park, which is popular but what about funding of maintenance of the trail that already exists? This section had some of the asphalt showing its age with the periodic shrinkage cracks giving that frequent bothersome bump. One hidden path bridge at the bottom of a hill had plywood covering over rotted deck boards, which at speed was very rough. But none of these maintenance issues should stop any one from coming to use the Oak Leaf Trail. I do recommend stopping at the coffee/ice cream store the trail parkway passes at Chicago Ave.
I am sure the rail to trail segment from Greenlawn Park was the former North Shore Interurban Line (to Chicago) that my folks took on their honeymoon to Milwaukee in 1944.

Ozaukee Interurban Trail (Route of the Badger)

Great trail; all paved. Lots of things to do along the way; many different stopping places available!

September, 2022 by jmglz

Great trail; all paved. Lots of things to do along the way; many different stopping places available!

Eisenbahn State Trail (Route of the Badger)

Love this trail! Can find several restaurants to eat at, play miniature golf, get a great cup of coffee all on the trail! Great trail!

September, 2022 by jmglz

Love this trail! Can find several restaurants to eat at, play miniature golf, get a great cup of coffee all on the trail! Great trail!

Lake to Lake Bike Trail (WI)

Love this trail! Beautiful ride; worth the trip to ride.

September, 2022 by jmglz

Love this trail! Beautiful ride; worth the trip to ride.

Lake Michigan Pathway

A very pleasant ride

September, 2022 by yospiff1

I started from a local community center near the south end, (asking permission to park my car there first). Also gave them a small donation when I returned. Most of this trail hugs the coastline, though the last few miles is along city streets. At the northwestern end of the trail, I found it joined up with a local rail trail, which runs from 3 Mile Road to Layard Ave. paralleling Douglas Ave., though it is not on Traillink. So I took that a few miles south and rode some city streets until I rejoined the Lake Michigan Pathway. In several places, the trail is not obvious or well marked, so keep your traillink app open to see where you are if you aren't sure. I recall one spot that looked like an alley past an industrial area, but it went down to the marina and the trail. Once past that, there are signs periodically to point you the right way.

Skokie Valley Trail (Lake County)

trail closed

September, 2022 by rickt597

The trail is closed at mile 6. There is little, if any signage for the detour. Take Old Elm Rd east to pick up the North shore trail to bypass the closure.

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