Explore the best rated trails in Watertown, WI, whether you're looking for an easy walking trail or a bike trail like the Levee Trail (Portage) and Peebles Trail . With more than 67 trails covering 758 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.
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.
Crushed stone was upgraded to asphalt by the end of 2022. Much smoother ride from end to end. Still absent a direct link into Lakeside Park.
I’ve ridden this trail several times. It’s well kept and beautiful!
I’ve ridden this trail several times. It’s well kept. Most of it is shady and fairly flat.
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
Rode the trail today from Beloit to Janesville and back. Of course, the trees were gorgeous! The path is paved the whole way. Much of the trail is along the river.
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
I forgot!! If you wanna ride the trail in its entirety.. the gap is about 8 miles
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.
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.
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