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 842 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.
Started in McHenry and went south. Did 33 miles round trip. McHenry to Crystal Lake lots of ruts and bumpy. Just north of Crystal Lake becomes a new, very smooth trail, but is extremely hilly with lots of turns. After going through a small section of downtown Crystal Lake becomes not as hilly to Algonquin.
Can confirm that many lazy and inconsiderate dog owners leave their dog's poops right on the trail, so keep an eye out for landmnes. Also beware that many people do not have their dogs on leashes, so have protection on you and stay vigilant. Beautiful farmland scenery starting from the Vandenboom trailhead heading west. Very flat, and occasional holes in trail possibly from critters. Nice that each road you reach from the trailhead is just about 1 mile so it's easy to gauge the distance you've walked.
I rode today from twining park to the town of Shultz. About 7 miles. The trail was in good shape. It was soft which made the ride a little more work. They just had a lot of rain though. I will come back and ride a different section soon. 3/25/25
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 ¿
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.
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!
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!
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.
New trail, is very smooth. Crossing streets is safe. Slight uphill grade west to east which makes return trip west easy!
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.
Ran parts of this trail recently. Easy paved trail through wooded area. Some shade in early morning hours.
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