Find the top rated inline skating trails in Freeport, whether you're looking for an easy short inline skating trail or a long inline skating trail, you'll find what you're looking for. Click on a inline skating trail below to find trail descriptions, trail maps, photos, and reviews.
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.
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.
Like all rails to trails, a good connector for locals but for bike touring, tedious. Boring, straight, only a few peeks of rolling farm land to catch your eye, when it wasn't on the trail - immediately in front of you. Sections of the trail are in jaw-jarring condition. Beware: with leaf litter you can not see the periodic holes, non existent bridge transitions, broken asphalt...you get idea. Sad that some entity can not repair these hazards. We def would not continue west, beyond Poplar Grove. Our bodies can't take it!
Rode from Colona to Bureau early October. The trail was dry and in good enough condition to average 9-10mph. There was lots of animal and bird life. I was surprised at how few people I saw. It was very peaceful. The only trail hazard of note were walnuts in the path. I did notice that there could be issues if it is wet. Drainage and mud could be a problem. I do ride a Surly Ogre with 29x2.35 tires and 45 lbs of gear on it. Navigation was not a problem.
Rode from Colona to Bureau early October. The trail was dry and in good enough condition to average 9-10mph. There was lots of animal and bird life. I was surprised at how few people I saw. It was very peaceful. The only trail hazard of note were walnuts in the path. I did notice that there could be issues if it is wet. Drainage and mud could be a problem. I do ride a Surly Ogre with 29x2.35 tires and 45 lbs of gear on it. Navigation was not a problem.
Such a beautiful path, partially in shade- partially open. There are multiple restrooms along the way, benches, picnic tables as well as a playground about halfway thru the trail! The paved path was mostly smooth and very easy to navigate. There is a few dips and hills but nothing challenging. Highly recommend!
Trail is really nice and taken care of. There are a a few sand traps along it tho. It’s mostly shaded until you reach the asphalt. Decent parking along it. I very much dislike the detour on this trail..it’s super hilly. Really regret coming to see the tunnel while still open.
The north most section has wonderful river views, picnic tables & benches. Then the trail runs along a heavy industrial area & is pretty ugly. The trail is also appears longer than the map indicates, but we turned back based on the map’s endpoint & poor scenery. TrailLink gives little mention to Eagle Point Park at the north end which is just amazing. If you just load/unload in their parking lot you will have missed the very best of the trail.
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