Find the top rated cross country skiing trails in South Milwaukee, 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 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.
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.
Both the North and South sections used asphalt and crushed stone surfaces. Care must be taken when riding on the crushed stone. The trail is nearly 12 foot wide and it is neatly groomed, however, the stone is just loose enough to keep bicycle speeds down. The rider who tests their speed traveling downhill and around the blind curves will surely tumble. The age of the asphalt in both sections varies from "newer" to "desperately in need of repair." The southern section actually has a warning sign just south of Fairfield Park.
The last two miles of the northern section in Round Lake Beach is loaded with perpendicular cracks in the asphalt causing a jarring ride even at slow speeds.
One must be cautious at the street crossings although some of the busier roads have traffic lights with designated pedestrian cross walks. The signage was ok, but could have been better.
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
Except for the 2 miles of crushed stone from Sheridan Road in Highland Park to County Line Road in Ravinia, the entire trail surface it asphalt!
The first 11 miles of the trail from the Wisconsin border is newer asphalt; no cracks or bumps to worry about. Just a smooth ride. The northern section of the bike path, however, is plagued with several street crossings, all of which must be approached with caution. There is little to no shade on the northern section.
The southern section of the bike path has a lot more points of interest including various sculptures along the trail, Metra train stations, the Ravinia Festival grounds and interesting cities to explore. The southern section offers much more shade, but also has a few street crossings as well.
The trail does give way to the road in both sections, but the signage is good for the most part. There are new mile markers on the west side of the trail every 1/2 mile.
The surface of this 8-foot wide trail seems to be crushed stone over an older asphalt base. It is a little tougher to ride than the typical crushed gravel surface. There are some "soft" spots throughout the length of the route, but still manageable. The trail is relatively flat with an occasional grade change. The scenery is mostly suburban backyard with a touch of industrial to the west. There is very little shade to protect you from the sun, but the openness is refreshing. Although most street crossings have minimal traffic, please take caution when approaching them. This is one of my "go to" rides.
I accessed the Powerline Trail at Cold Spring Road off of the Oak Leaf Trail. My ride on the new trail was very enjoyable and I found the route to be very pleasant passing by a number of neighborhoods. Compliments to the City of Greenfield and We Energies for their efforts to build this trail.
The route has a mix of crushed gravel at both ends and a nice wide asphalt trail in the middle. Be careful going through Saller Woods in the village of Rochester. The trail has been scarred by runoff, the gravel is loose and the hills are steep. Like a child clutching tightly to it's mother, the trail hugs Highway 36 for much of the ride. Although most of the trail is concealed by trees and brush, the sound of cars could still be heard. The trail in Burlington ends at a very nice park that has bathroom facility, water fountain and picnic tables under cover for a nice place to have lunch. The best part of the trail was "The Bunker." This bar & grill has a unique military-theme inside and outside its walls including a Vietnam Guard Tower and other military equipment.
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