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 Kenosha County Bike Trail and Kenosha Pike Bike Trail . With more than 75 trails covering 852 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

Root River Pathway

Challenging and adventurous

August, 2026 by kriekkoff_tl

The route was part road and part asphalt trail with a short section of crushed stone to keep it interesting. The asphalt trail surface was in better condition than some sections of the road. The signage, which could have been better, tested my navigational chops. In the end, though, I enjoyed the adventure. The route takes you right into downtown Racine. Beware the sidewalk section along 12th street. The center gap between concrete sections is wide enough to trap a smaller tire and bring the cyclist to an abrupt stop.

Peace Trail

Great Potential

August, 2026 by kriekkoff_tl

I had high hopes for this trail. I biked from Janesville to the end of the trail in the town of Beloit. The trail has great potential, but the trail maintenance for the first 4 miles out of Janesville has been severely neglected. The ride was unacceptably bumpy due to the several and continuous cracks in the asphalt. The trail south of the water treatment plant had been resurfaced and is in very good condition. The trail leaves the serenity of the shaded canopy of trees to the road in a couple locations. I don't mind the adventure, but one of the roads was busy and at high speeds. The signage could also have been better. The end of the trail in the town of Beloit offers a good cardio workout going up a steep grade. Your efforts are rewarded with modern restrooms and drinking water at the Welty Environmental Center.

Kiwanis Bike Trail

Janesville's Best Bike Trail

August, 2026 by kriekkoff_tl

Except for a section by one of the drainage tunnels where the asphalt is severely damaged, the trail surface is in good condition. I started my ride in Veterans Park and biked through a canopy of trees overlooking the scenic Rock River. The trail ends in the very cute Janesville Town Square. Although relatively short, this was my favorite trail in and around the city of Janesville.

Accordion

Long Prairie Trail

fun w/e-mountain bike

August, 2026 by km7phbf4j8

i’ve done this trail but it’s probably been 1214 years ago. Decided to take my E mountain bike and I’m sure glad I did some of. It’s pretty rough with rocks but overall it was fun. Nice long ride.

White River State Trail

Flat and Peaceful

August, 2026 by kriekkoff_tl

I rode the trail from Rosewood to Elkhorn. Most of the trail was flat and peaceful. Some of the crushed stone was washed away between Lyons and Burlington. Most of the trail surface was solid, but there were a few soft pockets where the stone accumulated from the wash out. Getting from the east section to the west section was tricky with no signage, but I was able to navigate the route using my i-phone GPS. If you like a flat, peaceful ride, then this is the trail for you.

Pelishek-Tiffany Nature Trail

All grass. Best for walkers not bikes.

August, 2026 by scb324

All grass. Best for walkers not bikes.

Brooke Street Trail

A lot of city riding

August, 2026 by y1htak2

We accessed this trail from the Lakeside Park trail. We were a little unsure of where to go until we got the areas which were well marked. It’s mainly city roads but there is a wide bike path off the road most of the time. Lots of neat old buildings.

This connected us to the Pioneer Trail which has 2 interesting roundabouts at the beginning of the trail. More city riding but you can stay off the street on the sidewalk.

Then we connected up with the Camelot trail. This trail starts out in the suburbs, you go past a pond and through a park. More peaceful ride.

Then you ride on a bridge over Hwy 45 / Fond du Lac Ave to get to the south end of the Prairie Trail which is by the Fond du Lac Waterworks Water Tower in a residential neighborhood.

We did this trail as part of the Fond du Lac loop trail system by going in a counterclockwise direction and following the Fond du Lac Loop signs.

We started on the north end of the Prairie trail at the Park N’ Ride/ Prairie Trail Lot on Winnebago Drive just off Hwy 151.

We took a right at the fork to bike the Peebles trail which ran into the Harbor view trail. We then took a detour through Lakeside Park on the Lakeside park trail. Then ended up going through the city on the Brooke street trail which ran into the Pioneer trail, another city trail. Which in its turn ran into the Camelot trail which took us over a bridge to the other end of the Prairie trail. A very nice loop. The trails are color coded and pretty well marked.

Harbor View Trail

Liked riding along the Marina, then on Lakeside Park Trail

August, 2026 by y1htak2

We accessed from Peebles trail. Paved.

Starts out on Harbor View Drive where you are supposed to use the bike lane in the street instead of the sidewalk. Then can go through a park if you want. Not sure of the parks name. There is a nice view of lighthouse and lots of boats.

Then took a detour through Lake side Park on the Lakeside Park trail which has nice bathrooms. Lakeside Park trail was very nice. There were some nice bridges over the streams, a covered bridge, an operating small train for riding around the park, and a barn.

We then got on a street going past the city yards where there was mulch, etc. I think it was the start of the Brooke Street Trail. Basically we followed other bikers.

We did this trail as part of the Fond du Lac loop trail system by going in a counterclockwise direction and following the Fond du Lac Loop signs.
We started on the north end of the Prairie trail at the Park N’ Ride/ Prairie Trail Lot on Winnebago Drive just off Hwy 151.
We took a right at the fork to bike the Peebles trail which ran into the Harbor view trail. We then took a detour through Lakeside Park on the Lakeside park trail. Then ended up going through the city on the Brooke street trail which ran into the Pioneer trail, another city trail. Which in its turn ran into the Camelot trail which took us over a bridge to the other end of the Prairie trail. A very nice loop. The trails are color coded and pretty well marked.

Peebles Trail

Peaceful short trail with mostly greenery on both sides

August, 2026 by y1htak2

We parked at the Park and Ride at Hwy 151 and Winnebago Drive which is the north end of the Prairie trail. We took the right fork to get on the Peebles trail. A short trail but peaceful. Trees and greenery on both sides of trail. Saw 3 deer. Connects you to the Harbor view Trail.

We did this trail as part of the Fond du Lac loop trail system by going in a counterclockwise direction and following the Fond du Lac Loop signs.

We started on the north end of the Prairie trail at the Park N’ Ride/ Prairie Trail Lot on Winnebago Drive just off Hwy 151.

We took a right at the fork to bike the Peebles trail which ran into the Harbor view trail. We then took a detour through Lakeside Park on the Lakeside park trail. Then ended up going through the city on the Brooke street trail which ran into the Pioneer trail, another city trail. Which in its turn ran into the Camelot trail which took us over a bridge to the other end of the Prairie trail. A very nice loop. The trails are color coded and pretty well marked.

Prairie Trail (WI)

Nice end to Fond du Lac Loop if you go counter clockwise

August, 2026 by y1htak2

We parked at the Park and Ride at Hwy 151 and Winnebago Drive which is the start of the north end of the trail. No bathrooms but there is a gas station/ restaurant on Winnebago drive which has a bathroom. This trail mostly runs along 151 but is buffered in areas by a pretty wide berm which sometimes had trees and other greenery on it. Other short areas separate you from Hwy 51 with a short concrete wall. Nicely paved. It’s pretty nice for a trail that runs along a highway. Better than Friendship trail.

There is a bench and drinking fountain at the south end by the Fond du Lac Waterworks water tower. We had fun turning on the bubbler and watching shoot about 8 feet in the air.

We did this trail as part of the Fond du Lac loop trail system by going in a counterclockwise direction and following the Fond du Lac Loop signs.
We started on the north end of the Prairie trail at the Park N’ Ride/ Prairie Trail Lot on Winnebago Drive just off Hwy 151.
We took a right at the fork to bike the Peebles trail which ran into the Harbor view trail. We then took a detour through Lakeside Park on the Lakeside park trail. Then ended up going through the city on the Brooke street trail which ran into the Pioneer trail, another city trail. Which in its turn ran into the Camelot trail which took us over a bridge to the other end of the Prairie trail. A very nice loop. The trails are color coded and pretty well marked.

Powerline Trail (WI)

Powerline trail is great!

August, 2026 by ljkjmk

Crossing roads can be tricky but most drivers are willing to let you pass.

City of Franklin Hike and Bike Trail

Busy Traffic

August, 2026 by kriekkoff_tl

Although the meticulously maintained 8-foot wide asphalt trail is short, one must cross W Forest Home Avenue twice. The traffic was fast and constant. I was lucky enough to attract a courteous driver who stopped for me, so I could make it across safely. Not a good trail for the young ones. The rating of the trail would have been 5 stars, but the traffic crossings brought it down a notch.

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