Find the top rated cross country skiing trails in Middleton, 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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I started the Jane Addams Trail at the RT 26 Junction and finished at the Wisconsin State border for a total of 32 miles round trip. Most of the trail felt like double track that was in very good condition due to the median of the trail being somewhat high grass, This did not make the ride difficult as both tracks are plenty wide for a gravel or hybrid bike to navigate with no issues.
I found the Orangeville trailhead to offer the most services along the trail. I'm sure the terminus in Freeport offers options as well but I did not explore that part of the trail. I also rode the Sugar River trail in Wisconsin and it is a great plus that one can ride the Jane Addams trail to the Beaver State Trail to the Sugar River Trail and beyond.
I rode the entire Sugar River Trail starting in New Glarus and ending in Brodhead totaling around 44 miles round trip. I found the trail to be in very good condition, mostly flat and finely crushed gravel with no major imperfections. The trail is mostly shaded and provided a wide variety of scenery from farmlands to quiet streams. There are a few road crossings but I encountered very few cars my entire trip.
The highlight of the Sugar River Trail are it's endpoints, both Brodhead and especially New Glarus are wonderful towns filled with charm and many options to dine at. I especially recommend staying in New Glarus at it makes accessing the Sugar River Trail as easy as a short ride if you stay in town.
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!
The trail is almost entirely crushed stone, except for the 1/2 mile of asphalt in New Glarus and the 1 mile of road in Brodhead. In fact, the term "crushed stone" is quite generous, since the trail is mostly two tire tracks with a grass median. Bottom line, the trail surface was solid even after a light rainfall and the grass on both sides of the trail as well as the median were neatly mowed. There was a nice mix of marsh, forest and open prairie. There was a mile marker on the west or south side of the trail every mile. The ride was very peaceful and quiet, except for an auction I heard while taking a break at the Albany trailhead. It was a nice change of pace to the ambient serenity. There were a few road crossings, but the country roads were rarely traveled. Both Broadhead and New Glarus were excellent anchors for this trail. There was lots to explore in both cities!
(08/19/26) - Another beautiful day and a beautiful trail. Rode from Tutty's Crossing (Freeport) to state line (WI). Trail in great shape with no major defects to get in your way for a relaxing ride. The small town and countryside/farmland vibe is just outstanding. Especially if you're a small town kid like me. It's a true getaway from life kind of ride for a couple hours. Very little trail traffic and the scenery is gorgeous. As always, don't forget to treat yourself at Union Dairy after the 34 mile round trip. A great reward for a long ride.
The asphalt surface had perpendicular cracks running throughout most of the trail resulting in a bumpy ride and over half of the cracks were filled with grass. The grass-filled cracks were actually preferred, since they helped cushion the ride almost eliminating the bumps altogether. Riding on the Levee, which separated the Wisconsin River from the local Portage population, gave me a euphoric feeling as if I were on "Top of the World." There was an interesting lock on the west side of the trail with an equally interesting watch tower. The trail was short, however, with an abrupt ending at the east end of the trail.
I started my ride in Sauk City on an overcast day and biked to the end of the trail in Merrimac. After reading previous reviews, I had high expectations for this trail. The asphalt surface was in perfect condition from start to finish. The trail was a wonderful mix of city neighborhoods, forest, farmland and open prairie. The art work scattered along the trail was a bonus as well as riding along the border of the Ho-Chunk Nation. At the start of the trail in Sauk City, it looked like a new pedestrian bridge had been built over the Wisconsin River. The trail to the bridge was closed due to construction. Even though the day was overcast, my high expectations for this trail were met. I will be back again.
I parked in the Mary Rountree Evans Park parking lot where the two trail segments are separated. Although the asphalt was older with some cracks, the ride was still acceptable. The trail meanders through a nice canopy of trees through the west segment and the western section of the east segment. Midway through the east segment, the route changes from trail to sidewalk (or road). The route takes you past the Circus World Museum and the corresponding historic buildings where all the circus animals were kept. There was lots to see during the short ride. I was fortunate that there were not many visitors that day and thus vehicular traffic was at a minimum.
The 8-foot wide asphalt trail is not in bad shape, but it does have manageable grass-filled cracks running perpendicular to the direction of travel in a few areas. Although there is a protective barrier, the entire length of the trail runs alongside a busy highway. There are a few street crossings with minimal traffic at best, but there are also two busy roads to cross. Fortunately, the intersections for these two crossings are controlled by traffic lights with pedestrian crossing signals. This ain't no rail trail, so the route has a few hills to master. On the plus side, the trail connects to the Peace Trail at the west end and the sides of the trail are nicely mowed.
I had high hopes for this trail. I biked from Janesville to the end of the trail in the town of Beloit. The trail has great potential, but the trail maintenance for the first 4 miles out of Janesville has been severely neglected. The ride was unacceptably bumpy due to the several and continuous cracks in the asphalt. The trail south of the water treatment plant had been resurfaced and is in very good condition. The trail leaves the serenity of the shaded canopy of trees to the road in a couple locations. I don't mind the adventure, but one of the roads was busy and at high speeds. The signage could also have been better. The end of the trail in the town of Beloit offers a good cardio workout going up a steep grade. Your efforts are rewarded with modern restrooms and drinking water at the Welty Environmental Center.
Except for a section by one of the drainage tunnels where the asphalt is severely damaged, the trail surface is in good condition. I started my ride in Veterans Park and biked through a canopy of trees overlooking the scenic Rock River. The trail ends in the very cute Janesville Town Square. Although relatively short, this was my favorite trail in and around the city of Janesville.
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