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 (WI) and Peebles Trail . With more than 67 trails covering 761 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.
As noted by the previous reviewer in June, 2023, this trail is now complete from its trailhead in Watertown to its junction with County Road F, south of Ixonia. It has been paved and open since October, 2022. Please update map. The map's satellite view actually shows the asphalt surface.
Picked up the trail by Holiday Inn and went North. Nice run with limited traffic… good paved path to put in a few miles
This section of trail was really pretty and easy to ride. My husband and I had lots fun exploring this trail! We also enjoyed crossing the covered bridge in Decatur.
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.
Rode from Mt. Horeb to Ridgeway and back. Beautiful countryside and the trail is great. All well kept. Can’t wait to go back!
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.
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