Find the top rated snowmobiling trails in Whitefish Bay, whether you're looking for an easy short snowmobiling trail or a long snowmobiling trail, you'll find what you're looking for. Click on a snowmobiling trail below to find trail descriptions, trail maps, photos, and reviews.




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Completed my final leg of this trail by riding from London to Cottage Grove today. Trail conditions were very good, however the bridges can use some maintenance. All have matting across them to assist in preventing flats, however watch your approach, there can be some serious bumps getting onto & off the bridges. Having ridden the entire trail now, eastern portion several times; it’s just my opinion that the western portion would be my recommendation. East of Douseman the trail is paved, however much of it is in need of maintenance to remedy cracks.
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.
The trail had a solid base with some loose gravel. I kept my speed down especially going down hills or around blind curves to keep from wiping out. There were hills to conquer, but the trail meandered through forest, prairie and around Mauthe Lake.
There was an undulating boardwalk to the north that was delightfully unexpected. The small town of Dundee had a couple of cool restaurants. Sorry, no crocodiles. :)
I happened to be in the neighborhood, so I biked the trail. I liked it!
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.
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.
I just rode from my Chicago home to Racine on the North Shore Channel, Green Bay, R McClory and Kenosha County trails. The McClory is newly paved and well signed from the Great Lakes Naval Station north to the state line. There are no facilities other than the occasional bench, and there are long stretches without any shade. Otherwise it is a terrific ride!
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!
I almost forgot to include this in my previous review:
If you do not like hills, DO NOT do either section of this trail.
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