Freeport, IL Horseback Riding Trails and Maps

440 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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Activities
Length
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6 Results
Activities
Length
Surfaces
Type

Cheese Country Recreation Trail

47 mi
State: WI
Crushed Stone

Hennepin Canal Parkway

104.5 mi
State: IL
Asphalt, Grass, Gravel

Joe Stengel Trail

7.9 mi
State: IL
Ballast, Grass, Gravel

Pecatonica State Trail

10 mi
State: WI
Crushed Stone

Rock River Parkway Trail

2.4 mi
State: WI
Asphalt, Concrete
Trail Image Trail Name States Length Surface Rating
If you’re looking for an invigorating motorized-trail experience, the Cheese Country Recreation Trail (aka the Tri-County Trail) won’t disappoint. If you’re on foot, hoof, or self-propelled two...
WI 47 mi Crushed Stone
The Hennepin Canal Parkway, administered by the Illinois Department of Natural Resources as a state park, follows an old towpath along a canal opened in 1907 and quickly abandoned due to competition...
IL 104.5 mi Asphalt, Grass, Gravel
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
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
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

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Trails by activity

Hennepin Canal Parkway

IL - 104.5 miles

The Hennepin Canal Parkway, administered by the Illinois Department of Natural Resources as a state park, follows an old towpath along a canal opened in 1907 and quickly abandoned due to competition...

Rock River Parkway Trail

WI - 2.4 miles

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...

Pelishek-Tiffany Nature Trail

WI - 6 miles

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...

Joe Stengel Trail

IL - 7.9 miles

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...

Cheese Country Recreation Trail

WI - 47 miles

If you’re looking for an invigorating motorized-trail experience, the Cheese Country Recreation Trail (aka the Tri-County Trail) won’t disappoint. If you’re on foot, hoof, or self-propelled two...

Pecatonica State Trail

WI - 10 miles

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...

Accordion

Hennepin Canal Parkway

IL - 104.5 miles

The Hennepin Canal Parkway, administered by the Illinois Department of Natural Resources as a state park, follows an old towpath along a canal opened in 1907 and quickly abandoned due to competition...

Rock River Parkway Trail

WI - 2.4 miles

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...

Pelishek-Tiffany Nature Trail

WI - 6 miles

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...

Cheese Country Recreation Trail

WI - 47 miles

If you’re looking for an invigorating motorized-trail experience, the Cheese Country Recreation Trail (aka the Tri-County Trail) won’t disappoint. If you’re on foot, hoof, or self-propelled two...

Joe Stengel Trail

IL - 7.9 miles

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...

Pecatonica State Trail

WI - 10 miles

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...

Accordion

Rock River Parkway Trail

WI - 2.4 miles

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...

Hennepin Canal Parkway

IL - 104.5 miles

The Hennepin Canal Parkway, administered by the Illinois Department of Natural Resources as a state park, follows an old towpath along a canal opened in 1907 and quickly abandoned due to competition...

Recent Trail Reviews

Great River Trail

Savanna to Thompson

May, 2020 by svalaika

Great smooth flat ride - our tandem was cruising! I agree with other posts, there’s a small section at the start that is buggy- lots of gnats. Bring sunglasses! It was cool and overcast but if it were a sunny day, bring sunscreen too!

Sugar River State Trail

OK in 2020

May, 2020 by johnson842

Rode from Monticello to Albany on my older mountain bike. No issues with upkeep. Great scenery and didn’t pass many other people on a holiday weekend.

Cheese Country Recreation Trail

Great trail

May, 2020 by r4g3.vlogs

I was hesitant to drive this far (about 2 and a half hours since I live in marshfield area.) because I have been disappointed with all other ohm trails. Was a great ride for me and my dirtbike. No sand was great and I highly recommend it to all dirtbike riders of all skills.

Accordion

Jane Addams Trail

Highly Reccomended

April, 2020 by kebunsha

Now that I have several to compare with, this trail is one of the finest. I generally only walk with my dog on it. The Orangeville BP Boco is a great place to stop for a snack, it has a sub/pizza counter and your can go back to the picnic shelter along the trail. Between O ville an Brush Creek Road, there is a butterfly nature preserve that was donated. I think its about 30 acres or more. The path is very well maintained. I generally do about 7 miles round trip per walk. Parking in O ville w/ porta potti, Buena Vista, Red Oak w/porta potti, Cedarville.

Kishwaukee River Recreation Path

Beautiful Riverfront

April, 2020 by raquel0827

Great path to walk with kids...not to long. Kids will love path entering Belvidere park lots to see, historical sites and bridges. Fun for the family.

Cannonball Path

changing the experience

April, 2020 by domccart

I have been walking on this path for almost 5 years. Most recently I have noticed that people living in the apartments along Leopold Way have started throwing trash and discarded furniture down the embankment bordering the trail. It really detracts from a sense of peacefulness on the trail. It is too bad there is no civic mechanism to warn the landlords or cite these morons.

Badger State Trail

Surgery River Trail

October, 2019 by psmietana51

Rode the SRT from Broadhead to New Glarus on Friday 10/25. Great scenic trail but some maintenance is needed, passed four down trees blocking the trail. Also some holes made by some critters you would not want to hit. Most of the mile markers were gone.

Glacial River Trail

A Return to Finish the Trail

October, 2019 by buehler868

I returned on one of those great Midwestern fall days to complete the portion of the Glacial River Trail south of Jefferson. I found the few miles that were in-fact a former railroad. The rest of the trail is in the WI-26 freeway corridor or on rural roads and city streets, but the trail is all paved.
The city of Fort Atkinson is very attractive with trail amenities including public art. I again found that the TrailLink map was a necessity as the signage on the tail is sparse.
My only negative is there is no need to do the on-highway portion south of N Wright Rd unless you want to continue to the connection to the Spring Brook Trail that will take you into Janesville.
For an out and back trip consider places where you can use the parallel old WI-26 for a different landscape view.

Pelishek-Tiffany Nature Trail

Clinton-Allens Grove

October, 2019 by suziesmithuw

Plenty of space to park stock trailer in gravel lot on Lake Shore Rd Clinton. Cute little covered bridge in small park with picnic tables was the start of my mule ride. There were trash receptacles, handicap accessible restroom & a wood post hitching rail. Many "sponsored" rest spots with wooden benches, picnic tables & some had roofs along the flat trail. Trail bed is wide, flat & firm as small crushed gravel & grass base. Views of plant/tree farm & rural properties after brief bit of SE side of Clinton. Mileage markers. Several blacktop road crossings. Easy, well-groomed trail. Small gravel lot at east end with trail map on kiosk. For lunch at Boar's Nest Bar ride Hill St (right uphill), stay right on Clinton St, quick Left along west side of the Park 1 block to stop sign Cty X. Ride directly across Cty X then straight across grass to cable picket line.
I-43 runs parallel to trail. Loud traffic but distance kept equines from becoming unnerved 🙂 Met a jogger, a hiker with a leashed dog on trail & 2 bicyclists at covered bridge. All were respectful of equines.

Cheese Country Recreation Trail

Nice ride

October, 2019 by blown86fox

If you are looking to take it easy and just go for a nice ride this is it. Smooth and simple. Very well maintained.

Hennepin Canal Parkway

good trail for autumn ride

September, 2019 by vj.capalbo

Road from Hickory Grove Campground for about 17 miles. Almost to Anawan and back. Previous night there was a very heavy rain but trail was fine. It’s definitely not pristine but totally rideable. Saw lots of wildlife and birds. Very enjoyable and relaxing as almost no other riders. Cool fall day was nice —there’s so little shade. Would recommend. The campground is great for RVs and they have cabins too. Beautiful location with massive trees

Glacial River Trail

Paved Trail Makes for a Nice Long Ride

September, 2019 by buehler868

The Glacial River Trail in the Rock River valley is untypical for Wisconsin state trails in that it is entirely paved and not a rail-to-trail. It has a great mix of segments in the WI-26 freeway corridor, city streets and rural roads, with some good grades. I did the north part of the trail from Jefferson to the junction with the Wild Goose State Trail. There are no services provided by the trail owner, but the trail is free to use. The signage for the trail-turns is minimal so the Trail-Link map downloaded on your smart phone is a must. I especially enjoyed my ride thru the river towns of Jefferson, Johnson Creek and Watertown, where I took the time to ride around the downtowns. I will come back someday to do the south portion.

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