Looking for the best trails around Oconomowoc?

Explore the best rated trails in Oconomowoc, WI, whether you're looking for an easy walking trail or a bike trail like the Peebles Trail and Brooke Street Trail . With more than 75 trails covering 837 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

Wild Goose State Trail

Lovely Trail

November, 2024 by the_masseuse

It’s pretty scenic, especially with the leaf colors. Also pretty busy! There’s parking on both ends. A lot of the trail is grass, not even gravel. The spot where it’s asphalt is very minimal. It’s awesome you can stop and ride through Horicon Marsh! Lots of kitties on this trail ¿

Badger State Trail

Serenity

October, 2024 by ggroth99

Coming from Chicago, we have only ridden this trail as a day trip and ridden from Orangeville, IL (Jane Addams Trail) to Monroe (Twining Park) and back. This stretch is on a slight incline most of the way from Orangeville to Monroe, so the ride back is a lot easier. Trail is well maintained, and mostly shaded by trees. Trail in Monroe proper was a little dicey due to no protection from the elements, a bit of a steep hill, and a lot of runoff from rain by 8th street. Crossing at 8th street is "interesting". Pit toilet in Orangeville, with a BP gas station right across the road, flush toilet in Twining Park. Went riding on 10/26, and saw a grand total of 5 other people the entire ride (2 bikers, 2 walkers, 1 jogger). Only trail I've been on where there were complete moments of silence, combined with some of the scenery, just absolutely breathtaking.

Jefferson County Interurban Trail

stunning and peaceful

October, 2024 by wilsonae

Just kept riding. Gorgeous fall day. Started at northern trailhead. Passed a few walkers and one other biker the whole way to the end. As noted it has been extended well past 2.2 miles. Lovely scenery and immaculate trail surface with lots of peaceful farms. My new fave!

Accordion

Long Prairie Trail

Disappointed

October, 2024 by deetiffanylb

Like all rails to trails, a good connector for locals but for bike touring, tedious. Boring, straight, only a few peeks of rolling farm land to catch your eye, when it wasn't on the trail - immediately in front of you. Sections of the trail are in jaw-jarring condition. Beware: with leaf litter you can not see the periodic holes, non existent bridge transitions, broken asphalt...you get idea. Sad that some entity can not repair these hazards. We def would not continue west, beyond Poplar Grove. Our bodies can't take it!

Glacial Drumlin State Trail (Route of the Badger)

Great trail, but there's a temporary closure

October, 2024 by sarahccaltvedt

We rode about 23 miles round-trip from the Waukesha trailhead on Oct. 12. The asphalt is in pretty good condition, with just a few bumps. However, when we got to the big curve around what used to be a field east of Dousman, we discovered that the field is now a massive construction site, and the trail is closed indefinitely, with no posted detour. We don't take our tandem on roads, so we turned around at that point. I assume that the trail is open west of the construction site, but don't know exactly where.

We didn't ride on the western portion of the trail that day, but it's one of our favorites, especially the part where you bike across the lake.

Powerline Trail (WI)

New trail, is very smooth. Crossing streets is safe. Slight uphill grade west to east which makes return trip west easy!

October, 2024 by lagerke

New trail, is very smooth. Crossing streets is safe. Slight uphill grade west to east which makes return trip west easy!

Glacial Drumlin State Trail (Route of the Badger)

There are several areas in which there are tire ruts and the trail is too narrow. Diffently not worth the daily fee of $5.00.

September, 2024 by dq82

There are several areas in which there are tire ruts and the trail is too narrow. Diffently not worth the daily fee of $5.00.

Hank Aaron State Trail (Route of the Badger)

Nice easy trail

September, 2024 by joenad55

Ran parts of this trail recently. Easy paved trail through wooded area. Some shade in early morning hours.

Prairie Trail (IL)

Water fountain removed

September, 2024 by elissasteglich

The water fountain noted on the map at Hillside Rd no longer exists. Looks like it was taken out.

Oak Leaf Trail (Route of the Badger)

Great trail!

September, 2024 by nadia.rasberry01

Well maintained trail, no garbage or anything on the path! Was great for walking with a stroller there was one roughest patch we hit but that was it. Amazing views and a nice breeze from the water. Very active trail, pretty busy area.

Ozaukee Interurban Trail (Route of the Badger)

This has to be one of the top 2 or 3 bike routes in the greater Milwaukee area.

September, 2024 by zero2epiphany

I have ridden this from Brown Deer to just a bit past Port Washington and still need to do the whole thing. On the Soutern side where it starts its no different than say, Zipline or the Brown Deer connector. But once you start getting close to Cederburg, it starts to shine, with a dip in scenery when you transition through Grafton. Then the trail SHINES BRIGHT right into Port Washington. This and Bugline are probably my favorite rides in the greater Milwaukee area.

Badger State Trail

Nice Views

September, 2024 by the_masseuse

Trail is really nice and taken care of. There are a a few sand traps along it tho. It’s mostly shaded until you reach the asphalt. Decent parking along it. I very much dislike the detour on this trail..it’s super hilly. Really regret coming to see the tunnel while still open.

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