Looking for the best trails around Freeport?

Explore the best rated trails in Freeport, IL, whether you're looking for an easy walking trail or a bike trail like the Kishwaukee River Recreation Path and Baumann Park Recreation Path . With more than 61 trails covering 603 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.

Recent Trail Reviews

Spring Brook Trail

Wonderful trail with interconnection options

August, 2026 by rturowski

We rode the trail northbound from Palmer Park. One caution I'd offer is it can be confusing because the signage reflects the Ice Age Trail more than the Spring Brook Trail. Possibly because this area seems to be convergent with several trails, including the Peace trail heading south (another very nice ride). Back to the northbound ride; once you go under highway 14, you'll find the trail splits, showing the Ice Age Trail turning left/westbound, and another trail (unmarked) heading due north. We decided to investigate the unmarked trail and found it very pleasant. The trail ended at East Rotamer Road, a short distance east of the left trailhead had we taken the other option by highway 14. We decided to ride E. Rotamer Rd. Westbound a short distance to the other trailhead and take it back to Palmer Park. Travel on Rotamer road was very easy. Designated bike lanes and light traffic helped considerably. In the end, the loop was a wonderful, enjoyable ride. As an aside, taking the trail south from Palmer Park, in the area of the Rotary Botanical Garden, you'll find the Peace Trail. One final note: there are several trail options in area; you might consider keeping your trail app active. My wife and I will definitely be returning.

Riverside Corridor Bike-Walking Trail

One and Done!

August, 2026 by rturowski

8/2/26 drove over an hour to experience, well lets say "much ado about very little" While from the trail preview it appeared interesting, this is one trail we'll not be returning to. Sorry Beloit, we bailed and went to Janesville's Ice Age Trail.

Military Ridge State Trail

Rough

July, 2026 by dgczzvmwyg

Rode from Dodgeville to Barneveld. The trail is pretty rough and feels more like a dirt road than a rail trail. Some sections are fine, but on other sections you really need to pay attention.

Accordion

Galena River Trail

construction 7 miles from the beginning

July, 2026 by christyfry14

Great trail, but rode it today and there is construction that is not passable at about 7 miles from Galena.

Sugar River State Trail

Good easy trail. Started in New Glarus and went foe about 2 miles.

June, 2026 by gann_chasity

Good easy trail. Started in New Glarus and went foe about 2 miles.

Hennepin Canal State Trail

Sterling to Tampico ride

June, 2026 by ericevan

Hennepin segment in this review: Sterling to Tampico
Bike: Specialized Sirus hybrid
Type of biker: casual, but I bike daily and can handle 25-35 mile rides
Weather: sunny, warm, upper 70's and dry.
Trail conditions: dry
Bike recommendation: no street bikes. Perfect for hybrid and mountain.
Other recommendations: sun protection, excess water, small protein bar or similar, phone, sunglasses, small towelette for sweat.


I started this trail at its entrance on the Sterling side of the Rock River.
Crossing the Rock was a nice starter. On the western dam side, a group of pelicans and their babies swam in the water. Can't say I've ever seen pelicans in Illinois before.
Once you reach the Rock Falls side the trail adjoins the Hennepin canal for the rest of the ride. In warm weather you're likely to see a lot of people fishing all the way down to the I88 underpass.
Heading south of I88 you aren't likely to see anyone. The trail is in decent shape being earthen based and I didn't see much more than small twigs on my ride south. There's easily a good 7-8 miles where you don't see much of anything manmade with the exception of crossing a road.
If you're a bird lover, this area will highly appeal. During my 25-mile journey I must have seen at least 50-75 orioles, a variety of blue colored birds, cardinals, several colors of finch, and a bird that has white tipped feathers that I've never seen before. I'm not a birder but they are beautiful to watch. The canal itself is clean with occasional turtles perched on logs.
There was only one spot on my segment with bathrooms, and that was closer to Tampico. The rest of the trail is devoid of bathrooms, benches and other amenities.

Some additional observations regarding this part of the trail:

Google maps indicate that a sunflower field is near the intersection of the trail and Star Road. There isn't. The area is entirely corn fields.

For rides longer than 5-10 miles, make sure to bring your own hydration and food. I bike daily and can handle long rides. But back here it gets rather warm. Water consumption for me was a little bit greater, and I even found a need to eat a protein bar to steady my energy level.

Importantly; a 25-mile ride back here will feel like well over 35. While the trail is in good shape, you do make a lot of dodges to avoid branches, twigs, holes, hanging bushes and other deterrents. The earthen path also slows your speed.

I didn't quite make it to downtown Tampico as I had original set out to do. My halfway point became Fargo Rd, at which point, I could see the little city of Tampico from a distance.

This leg of the trail completed my third on the Hennepin Canal Trail. It's a very peaceful trail with a lot of upside.
Cheers.

Military Ridge State Trail

Rider Beware

June, 2026 by nhx9h7gjw7

Love this trail but rode today between Riley and Brigham County Park and found the trail to be in extremely rough shape on either side of Mt. Horeb. Lots of ruts, giant holes and loose sand. Slow your roll and pay attention to utility flags and sticks identifying some of the bigger holes. Stay safe!

Glacial River Trail

a lot of road riding

June, 2026 by 47gkpg2wy5

We took this trail from the Wild Goose trail but had no idea we would be on so many roads. As you got closer to Watertown, you are also on the road. We personally try to avoid roads as much as possible so we didn’t like this part. We only went to Watertown from the North so I am not sure what the rest of the trail is like. The actual bike paths are great.

Lynn Boulevard/Westwood Trail

Nice trail in the park

May, 2026 by mjvolk95

I haven’t done the complete trail, only the part in the park near the rec-center. The portion in the park is paved, asphalt, and is mostly wooded. Plenty of turns and short climbs/decent. Visibility isn’t great due to trees and turns so not a top speed location. I did 2 laps in the park with my special needs son using his adaptive bike. Several other trail users were walking. There is a portion of this trail that runs along Lynne Blvd. That part is essentially a sidewalk or off-street path. We did not go on that portion.

Cheese Country Recreation Trail

Beautiful multi-use trail. It is the only trail open to ATV/UTV’s in Southern WI

March, 2026 by dougmayer11

Beautiful multi-use trail. It is the only trail open to ATV/UTV’s in Southern WI

Four Sisters Bike Path

Smooth, quiet ride

October, 2025 by idailey

Started this trail at the east end (Floyd Tilton Park). The trail is asphalt and in good condition. On the east side, the ride parallels the small Kyte River. As others have mentioned, you pass under the busier roads, which is nice. The trail swings around the high school, then south along 20th Street. There is an extension that heads west from Squire Landings, cutting through cornfields and then paralleling the RR tracks. I did an out-and-back on this section, then rode back to the starting point along 10th Ave. Traffic was low on a Saturday afternoon. After the ride, I went down to Rochelle Rail Park to absorb some local history and watch a couple of trains go by. I'd probably ride this trail more often if I lived closer.

Hennepin Canal State Trail

September Ride

September, 2025 by danielkarl1957_tl

My son and I rode from the visitor center east to the first aqueduct, about 20 miles round trip. It was beautiful day, we took our time, looked for turtles and stopped at a Casey's in Wyanet for lunch. Keeping to a healthy diet I went for sausage pizza, Yoo-hoo and an iced sugar cookie. The trail was rough, and rougher in spots but not a problem on my gravel bike with 40 mm tires. My son rides a Synapse with 35 tires and did it have a problem. If you ride a road bike or prefer smooth trails this might not be for you. we enjoyed it.

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Accordion

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