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 74 trails covering 841 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

Military Ridge State Trail

Military ridge trail 9/8/23

September, 2023 by jglass52

The weather went from to hot to to cold. 68 degrees, cloudy, threatening rain. I rode a MB from Ridgeway to a little east of Blue Mounds around 10 miles then 10 miles back to Ridgeway. Would have gone further but the weather was questionable. The trail is a little up and down and found loose sand and gravel on the grades. Otherwise the trail was in great condition, downed trees were all cut back and moved off the trail. Lots of trail bridges in the Blue Mounds area. All of the towns had places for food and drinks. Barneveld had toilets and picnic tables for resting. I did find a picnic table 3 miles West of Barneveld, so I stopped and warmed up some soup.
I would like to return but start my ride at Verona and ride to Mt Horeb or Blue Mounds.
Wisconsin has fantastic trails and don't mind paying the $5 trail pass. I'm from Illinois

Mascoutin Valley State Trail

Meh Pt. 2

September, 2023 by the_masseuse

I forgot!! If you wanna ride the trail in its entirety.. the gap is about 8 miles

Mascoutin Valley State Trail

Meh..

September, 2023 by the_masseuse

A nice trail, well kept, just a little boring. I’m sure it’s time to shine is true fall with the leaves in full force. 0 bathrooms and tons of little black bugs atm.

Accordion

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.

Military Ridge State Trail

We started out across the street from Riley Tavern and went all the way to Blue Mounds. Beautiful trail, well groomed and loved going through Mt Horeb. When we finished we were able to go to the Tavern for refreshments. Beautiful day!!

September, 2023 by danandjulie924

We started out across the street from Riley Tavern and went all the way to Blue Mounds. Beautiful trail, well groomed and loved going through Mt Horeb. When we finished we were able to go to the Tavern for refreshments. Beautiful day!!

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.

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.

Military Ridge State Trail

Enjoyable trail with some variety. Trail is in decent shape, except nearly all bridges are extremely rough shape, and also had many nails popping out.

August, 2023 by jmbahe

Enjoyable trail with some variety. Trail is in decent shape, except nearly all bridges are extremely rough shape, and also had many nails popping out.

Seven Waters Bike Trail (Route of the Badger)

Meyer Park to N Browns Lake Dr - 14m Round Trip

August, 2023 by theinonen

I really enjoyed my ride today! Started at Meyer Park in Wind Lake. I parked facing the baseball fields; bathroom building on the left, trail followed the baseball field around to the right. The connection to the main trail wasn't far. This is the one place the sign said Seven Waters Bike Trail. I turned right to head toward Burlington. It was crushed limestone but very packed down. My hybrid handled it great and I feel like road tires would be fine. The tail end of the crushed limestone section became crushed asphalt like someone else mentioned in their review. It's not as packed down; thicker, but still totally fine with the hybrid tires. I don't know how this section would be with road tires but it was also not very long. Once you hit Bunker bar on Beck Dr, it's paved all the way to N Browns Lake Dr which is south of Case Eagle Park in Rochester (it's probably paved further; this was where I turned around). There's a small road stretch at Beck Dr and it was clearly marked "Bicycle Route." Case Eagle Park is a great rest stop and again, had good signage. It has bathrooms, dog park, kayak/canoe launch; the river is right there and pretty for a pit stop. People were walking in the rocky section of the river and even fishing. All the trail signs (minus the one at Meyer Park) said Racine County Bicycle Trail. It's flat for the most part. I'm not super in shape and have taken just a few flat bike rides this summer, and this roundtrip of 14m was pretty easy. It was a warm day with a breeze. I felt there were a lot of shady parts on the trail. It was a Saturday afternoon in August and I passed some people but for the most part, I was the only one around (it was not crowded by any means). I will most likely do this again. I liked the variety with the scenery, the bridges, and that you ride through towns and a park for bathroom stops if needed. I felt plenty safe. I agree the map on the trail was not readable; the bike trail portion is completely faded. I just used Google maps because it detects the trail. Meyer Park where I ended also has a playground, pitching cages, and it looks like you can rent the barn for parties. Nice place!

North Mendota Trail

connecting trails

July, 2023 by michael216

This part of the trail connects several smaller trails, as they are expanding as part of the county bike paths. You can start near the new Bishops Bay subdivision or at Governor Nelson state park. It’s an easy trail, with some beautiful parts near the state park.

Muskego Recreation Trail (Route of the Badger)

Ride at your own risk

July, 2023 by alladdphoto

It might be OK for a mountain bike but not for a street bike. It was very uneven and patches of loose gravel that makes you loose control of you bike. This trail needs a lot of reconditioning to make this an enjoyable experience.

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