Explore the best rated trails in Winnebago, IL, whether you're looking for an easy walking trail or a bike trail like the Lake Geneva Bike Path (Route of the Badger) and Jane Addams Trail . With more than 67 trails covering 677 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.
Started in McHenry and went south. Did 33 miles round trip. McHenry to Crystal Lake lots of ruts and bumpy. Just north of Crystal Lake becomes a new, very smooth trail, but is extremely hilly with lots of turns. After going through a small section of downtown Crystal Lake becomes not as hilly to Algonquin.
Can confirm that many lazy and inconsiderate dog owners leave their dog's poops right on the trail, so keep an eye out for landmnes. Also beware that many people do not have their dogs on leashes, so have protection on you and stay vigilant. Beautiful farmland scenery starting from the Vandenboom trailhead heading west. Very flat, and occasional holes in trail possibly from critters. Nice that each road you reach from the trailhead is just about 1 mile so it's easy to gauge the distance you've walked.
Parked at the West end in the WalMart parking lot. Entire trail is paved and is mostly flat with some gentle inclines. The first 4.5 miles is along Northwest Hwy (rte 14). This entire section is full of litter either in the grass between the road and path or along the farm fields. SO much garbage. The path turns towards Veteran's park in Crystal Lake just past MCC. The last 2.5 miles is along the high voltage lines that you can hear buzzing. Great path if you are commuting to and from MCC but not a pleasant path for an afternoon ride.
The 10-mile stretch of the trail from st. charles to elgin is mostly asphalt with a few short lengths that are crushed stone. The trail is in good shape generally with hardly any heavings in the pavement. The scenery is mostly natural woods and very scenic. Between st. charles and the town of south elgin the river takes a big bend around a high bluff and the trail goes down a long hill as you travel north and over 2 bridges. Near the town of south elgin there is a trolley museum with tracks alongside the trail that working trolleys use on the weekends. Between south elgin and elgin there are many hilly sections. It can be a challenging but worthwhile ride.
I rode today from twining park to the town of Shultz. About 7 miles. The trail was in good shape. It was soft which made the ride a little more work. They just had a lot of rain though. I will come back and ride a different section soon. 3/25/25
I've cycled and jogged this trail since 1986. It eventually links up to the Badger/Jane Adams trails and continues onto Madison to the Capital City Trail or cut off to the Military Ridge Trail.
I've met people that use this trail for hundreds of miles. People from throughout the country. Always safe and people occasionally camp along the trail while hiking. Amazing flora until late October.
I use it as a perfect half marathon training trail. Soft on the knees and legs.
Monticello to New Glarus and back is approx. a perfect 13.1 miles. With
a couple service stations in New Glarus along the trail to refurbish your fluids. Unfortunately, the Stewart is closed and projected to open in 2027.
A short detour on the road needs a little caution on a curved hill. But safe as the road is rarely used.
Nice trail head near Rt. 20.
This was used by myself and my son to train for a marathon and halves.
The shade is great and the same trees and shrubs cut the wind down.
So if you carry your fluids or have someone to cycle along side you, this is the trail you want to train on.
From Rt. 20 to Orangeville and back is approx. 20 miles. With trail on each end if you want to train a greater distance.
The crushed limestone is easy on the feet and legs.
I cycle it dozens of times a month. But training for any event is perfect here.
Rode late September right before official hunting season. Not a lot of people on it. But to be safe, we carried blaze orange. parked at Wes Block trailhead as the long road out from Freeport is just bad trail riding next to an interstate. Trail is dirt, with some repairs and gravel. Rode up to the state line and the Badger Trail out and back. There were some beautiful spots, but also some lone wolves walking the trail looking sketchy and a hunter on an ATV at twilight. If you wanted to do an overnighter up to Madison and back the next day, you could park at the hotel right near the WB trailhead. Not sure I would do this trail again though as it was a long drive for a day ride from the suburbs.
Coming from Chicago, we have only ridden this trail as a day trip and ridden from Orangeville, IL (Jane Addams Trail) to Monroe (Twining Park) and back. This stretch is on a slight incline most of the way from Orangeville to Monroe, so the ride back is a lot easier. Trail is well maintained, and mostly shaded by trees. Trail in Monroe proper was a little dicey due to no protection from the elements, a bit of a steep hill, and a lot of runoff from rain by 8th street. Crossing at 8th street is "interesting". Pit toilet in Orangeville, with a BP gas station right across the road, flush toilet in Twining Park. Went riding on 10/26, and saw a grand total of 5 other people the entire ride (2 bikers, 2 walkers, 1 jogger). Only trail I've been on where there were complete moments of silence, combined with some of the scenery, just absolutely breathtaking.
Have ridden this trail multiple times over the past couple of years. Generally ride from the trailhead by Hwy 20 to Orangeville. Trail is well maintained and generally flat, and fairly empty of people, a few joggers on the South end. As with all the limestone trails, there's a few holes here and there from the local furry creatures. Pit toilets at Hwy 20 & Orangeville, a portolet at Red Oak. There's a BP gas station right across from the pavilion in Orangeville. Specific highlights are the old buildings from the railroad in Scioto Mills, and saw sand cranes inhabiting the wetlands south of Orangeville.
Rode our hybrids from Freeport Public Library to trail and followed it to the state line. Found it to be well maintained, flat and very little bike traffic. We biked on a Friday morning. FYI the library has paper maps of the trail.
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