Looking for the best trails around Caledonia?

Explore the best rated trails in Caledonia, WI. Whether you're looking for an easy walking trail or a bike trail like the New Berlin Recreation Trail and Seven Waters Bike Trail (Route of the Badger) . With more than 69 trails covering 831 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

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.

Deer Grove Trail

not a fan

September, 2023 by 97ca5crqis

Once a great hiking preserve no not so much. It is evident that funding just isn’t there for a quality site like other county trails. They still have a chain link fence blocking off an area damaged years ago which looks like an excuse to no maintain and save money. As it’s been under repair for a good 10 years. Deer grove was my backyard growing up and it was an amazing preserve it’s sad to say that it is no more

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.

North Branch Trail

15 mph bike speed limit is like "No dunking" signs at a basketball court.

August, 2023 by xegroeg_tl

15 mph bike speed limit is like "No dunking" signs at a basketball court.

North Branch Trail

Recently has become hostile to road cyclists

August, 2023 by drf6gg44wn

This bike path was once was a great safe car-free detour for road cyclists traveling north from Chicago, bypassing busy Ridge/Sheridan Rd.

With the addition of 15 mph speed limit signs and people yelling "slow down" and shaking their fists constantly to anyone in lycra, it's become clear cyclists are no longer welcome on the "trail".

It's so unfortunate that people behind a bike path would work actively to discourage cyclists from using it.

If you're a seasoned cyclist looking to get training in I suggest avoiding unless it's late fall, winter, or early spring.

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!

Des Plaines River Trail

loved it in spite of the gravel

August, 2023 by kjclow

Biked this trail twice over the weekend. Started both from Independence Park. First day went north to the Wisconsin state line, almost. Second day went south to Libertyville. Fun rides with no one on the northern loop on a Friday afternoon. Sunday on the southern loop was more crowded. The two negatives are the complete lack of restrooms down to libertyville. If there are any they are not marked from the trail. The other negative was riding crushed rock on a road bike. Was not prepared for that and hit a few soft spots that tried to suck me down. I prevailed and managed around 68 miles for the two rides.

Des Plaines River Trail

Des Plaines River Trail (Cook County) from Tuohy Ave to Lake-Cook Rd

August, 2023 by jcook1950_tl

As noted by other reviews, this segment of trail is rugged. However, if prepared for the conditions it can be viewed as an adventure. The trail is under construction from Devon Ave to Tuohy Ave (south of Devon down to North Ave I knew it might be impassable due to recent rains) but from Tuohy going north to Golf Rd the trail was decently dry (rode several days after moderate rainfall) as it went through the forest preserves. An undeveloped rail crossing creates a trail gap between Golf and Central Ave so there is an unmarked alternate route along East River Rd with narrow shoulders and bad paving that leads into Beck Lake preserve to pick up the trail again. North of Beck Lake the trail is fairly good up through River Trail Nature Center (worth visiting)/Allison Woods. An unsignaled crossing of busy Milwaukee Ave (Rte 21) is then needed and the trail starts again on Winkleman (frontage) road between the Crowne Plaza and Hilton hotels. Between Milwaukee Ave and all the way to Lake-Cook Rd it is very challenging even when fairly dry but with good natural scenery and bird/animal sightings.

Fox River Trail (IL)

fox river trail…

July, 2023 by tjmodd

My husband and I rode this trail round trip (82 miles) with our road bikes. We had breakfast at “Oak and Bean” before the journey (highly recommend; breakfast sandwiches on homemade bagels & homemade bread; custom coffees). and headed north from there. We benefited by downloading the route from the Rails to Trails App as FVT has other trails that branch off from it. We took a few wrong turns but we were able to navigate back to the trail because we had the map from R2T. There are a few spots where the trail is connected by streets going through neighborhoods. Over all this is an excellent trail. Some areas are rough due to cracks in the cement or raised areas due to roots, but it’s not terrible. I recommend this trail . I will ride it again. It’s worth my drive from Grand Rapids MI. Also. Try the “Coffee Garden onMain”. It’s a great restaurant newly opened. You’ll have to bike a few extra miles past Algonquin, but it’s worth it. It’s right off the trail to the right when you hit. A busy intersection.

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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