Explore the best rated trails in Caledonia, WI, whether you're looking for an easy walking trail or a bike trail like the Seven Waters Bike Trail (Route of the Badger) and New Berlin Recreation Trail . With more than 70 trails covering 826 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.
Be aware. Signage not good 1st part of south end (where we began).
Trail Link map + GPS very helpful. Since signs are more in keeping w/ biking, than nose on phone, a suggestion: At decision points pls post signs, rather than down the road when you’ve luckily made a correct turn. Once through that the South end chains thru parks, many charming bridges over The Root River. North end signage was elusive too. We park near Zoo, biked along shore line, cut West to pick up trail just west of Main Street bridge and enjoyed 90% of the ride back toward North/car. A leisurely and scenic ride except for the navigation guessing game at beginning and end.
We rode this trail along with the Stone Bridge Trail. The asphalt needs some repair but still a nice trail.
Officially part of the Milwaukee County Oak Leaf Trail system, this connector joins the Oak Leaf loop at Brown Deer Park and meets the Ozaukee Interurban Trail seamlessly at County Line Road. Combined with the Oak Leaf’s Lakefront, River Line and Zip Line segments, they provide straight, smooth pavement on railbed between downtown Milwaukee and Cedarburg, and beyond.
On a perfect weekday morning in early October I experienced by bicycle the South Shore portion of the Oak Leaf Trail.
I parked in the Grant Park Beach parking lot in South Milwaukee and headed north to Cupertino Park and then back, a distance of about twelve miles. Even though it was such a short ride it took me over two hours since I had to frequently stop for the awesome photo ops. The views of the lake and the Milwaukee skyline are sensational!
The trail is obviously beloved by the community. Not only were there plenty of other bicyclists, but there were a tremendous amount of friendly pedestrians walking their dogs or getting their steps in, especially in Bay View Park.
The South Shore portion of the trail has so much to offer: woods, tree lined streets with charming homes, wildflowers, squirrels, geese, shoreline, lots of curves, five parks, yachts, and plenty of benches to take in the marvelous views of Lake Michigan and the downtown skyline. Besides the lake views, I especially enjoyed the curvy trail covered in golden leaves through the woods of Grant Park.
TWO WORDS OF WARNING:
1) There are hills.
2) There are cracked and uplifted portions of trail through the woods of Grant Park due to tree roots. They will effectively work like speed bumps and slow you down a bit.
However, all in all, this is an enjoyable ride and certainly worthy of your time and five stars!
This trail was actually a former C&NW railway that served Lake Geneva and terminated in Williams Bay. Service to Williams Bay started in 1888 and ended in 1965. Service to Lake Geneva ended in 1975. Thanks to Maxine Thoorsell for starting the conversion of turning this former railway into a nature trail. It is an easy grass covered walk and the trail is 1.7 miles in length. You can also access the trail at the boat launch to the west...behind the barn. A separate trail that is part of this former railway extends from Williams Bay Northeast up to Hwy 50 in the Kishwaukeetoe Conservancy
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.
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
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 !!
Great trail for walk surface and natural sites.
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.
15 mph bike speed limit is like "No dunking" signs at a basketball court.
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