Find the top rated cross country skiing trails in Oconomowoc, whether you're looking for an easy short cross country skiing trail or a long cross country skiing trail, you'll find what you're looking for. Click on a cross country skiing trail below to find trail descriptions, trail maps, photos, and reviews.
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It took some doing to find the trailhead of the actual “trail” part of the ride. Dewitt Road in Oostburg was the start of the paved trail. Parking was available along a nearby neighborhood road. No parking lot. From there you can ride south with only one little part on the road around a factory just past Cedar Grove. There is a nice shelter with a porta potty at the Cedar Grove depot. Unfortunately we had to turn around short of Belgium so have to leave the rest for another day.
Scenic, very pleasant ride today. Farmland, lots of bridges, packed gravel so no surprises. Parked at the Elkhorn trailhead and biked to Burlington and back. Note: the DNR site says there's a bridge out, as of 9/27/26 - there are no bridges out. Really nice ride and great way to spend a 70 degree and sunny day in late September.
If you are looking for a quiet, flat, and peaceful ride, then this is trail for you. The route takes you deep into the woods, out in the open prairie or farmland, and through a few small towns. The trail is mostly a crushed gravel road with a grass median. The sides of the trail and the median were nicely mowed. The were no mile markers and there were a couple of long stretches with no road crossings. Since my ride was in the fall with temperatures in the 50's, there were no mosquitoes.
The four areas with fallen trees noted by the previous review were all cleared.
There was underground utility work being done on the west side of the trail over the entire length of the it from Highway 60 to Fond du Lac. The use of small cranes with track systems for the utility work had literally made an impression on the trail surface. Most areas were patched up reasonably well, but the section between Waupun and Burnett was poorly patched resulting in an unacceptable bumpy ride.
I also encountered one too many wrist-jarring chipmunk holes that were randomly dispersed throughout most of the ride.
There were enough bathroom facilities, but there were absolutely no water sources, so bring a good supply of drinking water.
As part of the 8-trail Fond du Lac Loop, the Brooke Trail was the most adventurous. The 12-foot wide asphalt trail hugs the side of Brooke Street at first. The asphalt surface is older with some sections burdened with cracks causing a bumpy ride. The trail takes the adventurous rider through a mix of not only industrial and newer development, but also through a poorer section of town as well. The entire loop is well-marked. Although the map shows the trail ending at Dixie Road, it actually continues west on Dixie Road, then south on Hickory Street where it ends at Pioneer Road. The "Loop" then continues east along the Pioneer trail.
This trail is one of 8 trails that are part of the Fond du Lac Loop. The Harbor View trail is flat, smooth and beautiful. This trail, along with the Lakeside Park trail that it connects to, are the most scenic portion of the "Loop" and the most rewarding to ride.
I rode the trail from Sheboygan to Fond du Lac and this was a hilly ride from start to finish. The route between Greenbush and Sheboygan did have a few sections that were flat, but the route between Greenbush and Fond du Lac resembled a roller coaster. I would race down one hill, so I could minimize the effort needed to get up the next.
The asphalt surface overall was in good condition and the sides were nicely mowed. The trail surface between Greenbush and Fond du Lac was especially smooth.
The scenery to the south of the trail was a mix of farm field, prairie, woods, and rural back yards. The scenery to the north was always highway 23 and there was no escape from the noise either. Take caution approaching street crossings and bring a good supply of water.
The trail starts unassumingly in a residential neighborhood to the north and winds its way through Carthage College before bursting out of a canopy of trees into a spectacular, unobstructive view of Lake Michigan. The trail hugs the coast and meanders through a series of gorgeous parks. Just when your senses have almost reached their limit, you find yourself riding along Harbor Park filled with an assortment of sculptures, museums, and marinas. The Park is electric!
This was the most enjoyable ride I have ever taken. I will be back!
There are two cautionary notes, however.
1. The city roads between Poerio Park West and upper Alford Park are in horrible condition. Maybe avoid this northern section altogether.
2. The trail that goes south from the 50th Street bridge as you enter the Harbor is actually a staircase. I missed it the first time, but realized it on my return. There is a very steep embankment with a thin bike path next to the stairs, if you want to risk it.
The 10-foot wide asphalt surface is still in good shape. The trail hugs the road at the north end, but eventually disappears behind suburban backyards under a wonderful canopy of trees. There are a few pesky road crossings, but not bad. The trail is short, but flat and easy to ride. This is a great connector to the Kenosha County Bike Trail or the Kenosha Pike Bike Trail.
9/12/26 Rode the newly opened interconnecting portion linking Watertown to Oconomowoc, Wisconsin. We started at the westerly trailhead of the Lake Country Trail in Oconomowoc, then rode west across the new portion all the way to the Watertown westerly Jefferson County Interurban Trailhead. This trail has one bench along the route and no facilities except at the trailhead in Watertown, which are very nice, and no parking points along the route except at the west and east trailheads. The route itself is nicely pave, wide and maintained; however straight as an arrow and the scenery is essentially all agriculture, which for the area is to be expected. Our round trip mileage was 27 miles on our odometers. One note for anyone bridging the gap between the easterly end of the Jefferson trail and the westerly trailhead of the Lake Country Trail; there's approximately a 1/2 mile road portion bridging the two locations which could be marked better. The other improvement might be mile markers, or a least road identification signs at crossings along the way. At the end of the ride though it was a pleasant trip, and an addition to the many trails we've traveled across Wisconsin.
This recently completed trail now runs all the way between Watertown and Oconomowoc! Eleven plus miles of really nice asphalt, passing thru farm fields and crossing the Rock River -- it is a treat. I rode a full round trip twice in the last weeks, and it was great. Check out the great Mexican dishes at Taqueria Maria's in Watertown, just a mile or two past the Watertown trailhead. Try it out!
But we had a nice road ride from just N of the power plant (good bathroom at the park) to the southern end of Kohler-Andrea S. P. Shady, mostly good road shoulders, about half marked for bike lane or fog line and 3’ paved shoulder. Some turns not marked with bike route signage so watch your GPS. Maybe 4 or 5 vehicles per mile. Only actual trail is 50 yards at SP entry. Beyond SP no shoulders so tuned back, got about 14 miles
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