Freeport, IL Horseback Riding Trails and Maps

664 Reviews

Looking for the best Horseback Riding trails around Freeport?

Find the top rated horseback riding trails in Freeport, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.

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Length
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6 Results
Activities
Length
Surfaces
Type

Rock River Parkway Trail

2.4 mi
State: WI
Asphalt, Concrete

Cheese Country Recreation Trail

46.4 mi
State: WI
Crushed Stone, Dirt, Gravel

Hennepin Canal State Trail

93 mi
State: IL
Asphalt, Grass, Gravel

Pecatonica State Trail

10 mi
State: WI
Crushed Stone

Pelishek-Tiffany Nature Trail

6 mi
State: WI
Dirt, Grass

Joe Stengel Trail

7.9 mi
State: IL
Ballast, Grass, Gravel
Trail Image Trail Name States Length Surface Rating
The Rock River Parkway Trail in Janesville runs between Rockport Park and S. Jackson Street bridge on the north side of the river. Here, at the trail's eastern terminus, you can easily link to Spring...
WI 2.4 mi Asphalt, Concrete
Most suited for ATVers, snowmobilers and motorized trail-bikers, the Cheese Country Recreation Trail, also knowns as the Tri-County Trail, spans 47-miles through Wisconsin’s rugged Driftless Area. On...
WI 46.4 mi Crushed Stone, Dirt, Gravel
The Hennepin Canal State Trail stretches for 93 miles in northwest Illinois along an old canal towpath. The trail is administered as a State Park by the Illinois Department of Natural Resources, and...
IL 93 mi Asphalt, Grass, Gravel
The Pecatonica State Trail is never far from water as it takes the easygoing Bonner Branch Valley through the rolling hills and rocky bluffs of southwest Wisconsin’s Driftless Area, a region that the...
WI 10 mi Crushed Stone
The Pelishek-Tiffany Nature Trail runs for 6 miles along an abandoned railroad corridor, between the towns of Allens Grove and Clinton. The trail is open to snowmobiles, cyclists, horseback riders and...
WI 6 mi Dirt, Grass
The Joe Stengel Trail follows an old railroad corridor for 7 miles between the town of Polo and the much smaller community of Woosung. The trail corridor traces farm country along a route scattered...
IL 7.9 mi Ballast, Grass, Gravel

Recent Trail Reviews

South Connector Trail

This ain't no rail trail

September, 2026 by kriekkoff_tl

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.

Peace Trail

Great Potential

August, 2026 by kriekkoff_tl

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.

Kiwanis Bike Trail

Janesville's Best Bike Trail

August, 2026 by kriekkoff_tl

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.

Accordion

Long Prairie Trail

fun w/e-mountain bike

August, 2026 by km7phbf4j8

i’ve done this trail but it’s probably been 1214 years ago. Decided to take my E mountain bike and I’m sure glad I did some of. It’s pretty rough with rocks but overall it was fun. Nice long ride.

Pelishek-Tiffany Nature Trail

All grass. Best for walkers not bikes.

August, 2026 by scb324

All grass. Best for walkers not bikes.

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.

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!

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Accordion

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