Freeport Horseback Riding Trails and Maps

376 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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Type
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, Crushed Stone

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, Crushed Stone
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...

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...

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...

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...

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...

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...

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...

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...

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...

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

Cheese Country Recreation Trail

Easy ride

May, 2018 by bearsfans51

Easy ride from Monroe to Mineral Point. Weekends on trail are too busy. Plenty of places to get gas and/or supplies approx every 5-7 miles. DNR and Sheriff always on trail. Trail can have some serious jagged rocks so bring repair kit or spare. Watch out for erosion some serious wash outs in places.
Most of the small towns are very welcoming to atv/utv except Mineral Point (most Mineral Point businesses only take cash) experienced rude and unwelcoming town folk / businesses and an atv route that does not let you drive or park in the business area. You have to park on the atv route which runs on the outskirts of town then just stops at a gas station..you park blocks away and walk in. Most businesses closed during the week in Mineral Point..think they would want, need and welcome the revenue...guess they don't. Bring cash if you decide to visit. Check out Leftys and Ponchos in Monroe great food and people!

Galena River Trail

Fall 2017 Update

November, 2017 by m.hoffmann

With 60 degree weather the day after Thanksgiving I took a quick ride down the trail to the south end. I was pleasantly surprised with the progress being made on the trail extension. The 2-3 mile extension is carved into the side of the hill high above the railroad tracks. It traverses a new 60 ft bridge before descending down and running parallel to the service road. It looks to be complete to S. River Rd or Aiken sometime early in 2018.

Badger State Trail

bager state trail

November, 2017 by stuff6

Rode south out of fitchburg. About 5-6 miles south this turns into a limestone path. I rode it in november so maybe its better in the summer but its no skinny tire road bike route. Was nice until then.

Accordion

Pecatonica State Trail

Not bad

October, 2017 by polarismagic

trails were not bad. it is limestone or gravel. Encountered atvs and they gave plenty of space or stopped and waved.

Sugar River State Trail

Frequent rider

October, 2017 by bruce_d

The trail needs more mileage markers. Only miles 1,2,3,5,8,and 10 are posted. It would be helpful to know where on the trail you are at and how far it is to each end. Mostly flat with gopher holes present in many places. Beware of the wild Parsnip growing alongside the trail.

Hennepin Canal Parkway

A Nice Ride

September, 2017 by mcaples67

Road 60 miles (30 out and back) from trailhead at Rock River in Colona. We brought our road bikes (23mm tires), expecting paved trails. It was slow going, but certainly doable. The trail is definitely in need of repair and maintenance. It is flat, peaceful and quite beautiful. The canal history and artifacts (locks, etc) are a very interesting perk.
Fortunately we packed extra water. We had trouble finding water stops along the way. There was a fountain at the lock (14 miles from the trailhead) but it was not working in late September even though it was almost 90 degrees.

Sugar River State Trail

NO MAINTENANCE!

September, 2017 by mickmcclain

I love riding this trail as it's yards from my house, but honestly, the DNR hasn't done jack shXX to maintain this trail for years! It is full of holes and ruts. DNR solution to holes is simply dump sand all over them. That way if you survive hitting the hole, you can always injure yourself by having a wheel slip away from you in the sand! Was on the trail yesterday afternoon, tree branches all over the place covering the trail... full of ruts. I don't understand why the DNR won't roll the trail in the spring when the ground is soft to even it out some.

I don't mind buying a trail pass every year for my wife and I, but it's high time some of that money went into real maintenance. Another big problem is that the trail to bridge transitions are terrible. You hit the bridge and the first plank is 3-4 inches above the ground on MANY bridges! Again, enough is enough. Fix it already!!!! I live in Green County and love the trails, but this one is basically unusable since maintenance has been ignored for so long.

Pecatonica Prairie Trail

Not your Sunday afternoon dally...

September, 2017 by flmasterman

It was the first day of Autumn and 93° when my riding buddy and I returned to the trailhead in Winnebago in the late morning after travelling west to a private lane just short of Farwell Bridge Road and back - 19.13 miles indicated on my bike's computer.

This bike trail may not be the most scenic, and may not be a 'real' Rail-Trail, as it seems to parallel the old rail line rather than use it, but it's still better than riding the streets in town for this guy. Lots of sunshine under the sparse canopy of power lines meant lots of water consumed on this hot day.

It is paved only in short sections - in the towns/villages of Winnebago and Pecatonica, as well as in the vicinity of Highway 20, where it appears that a very large paved parking lot has been recently constructed on the north side of the road. Other than that, I would classify this as a 'fair-to-rough' hard-pack surface trail.

Some have commented negatively about the loose/sandy section. That section will certainly get a rider's attention, but this 68 year old on an eight year old, 'bottom-of-the-line' Trek Mountain Bike, rode through it without mishap, as did his younger riding partner on a Hybrid Giant bike.

This trail is definitely not for the rider that wishes to just cruise along and visit, while gawking. One must pay attention and watch for the mini-sinkholes, as well as the variations in trail surface. I am a nature lover however, and 'roughing it' has always held a very special place in my heart. This trail is what it is. If one wants a paved path, choose another. If one wishes for a little private time in nature and reap the joy and benefits that comes along with riding a bike, then this 'less than groomed' trail might be just what the doctor ordered.

I also need to point out that the signage along this trail is excellent - every public road crossing is clearly marked with road/street names and stop signs.

A quick stop at the small gazebo along the river near the fairgrounds in Pec will provide one with an interesting history of the river and the Pecatonica Grist Mill of days past.

In summary... I will be returning to this trail to see what is at Farwell Bridge Road and beyond, as well as to complete the ride to Rockford and see what's up on that end.

As stated previously, "This trail is what it is". Take it or leave it.

Pecatonica Prairie Trail

Went East from Winnebago.

September, 2017 by jorourke61088

Three miles from Westfield road in Winnebago to meridian road where it ends. They are doing construction on a sewer main so I am not sure you can go on it during the week past Weldon road. It looks like they've widened it to move heavy equipment through. There are a couple of rough spots but nothing you can't get through. Fields on both sides and flat.

Harlem Township Bike Path

Great place to walk!

September, 2017 by expressionsbylindsey

I come to the Harlem Township Path almost everyday. I walk with my dog. Always very well maintained. The 1.6 miles is great and my son loves to run around the track as well. The playground and other sports options in the park are awesome as well! Wonderful park all around :)

Hennepin Canal Parkway

Nice ride along Hennepin feeder canal

September, 2017 by hilbertdr

We rode from the trail head at Lock 22 (where CR 300E crosses the canal) up along the feeder canal for about 14 miles. The trail was in good shape for most of the way, mostly paved, and it was enjoyable ride. North of the Rte 92 crossing the trail quality deteriorated markedly and it was single track dirt through weeds and grass. We turned around at Osage Rd because of the trail condition. We tried riding west from Lock 22 but gave up after a little over a mail. It wasn't that bad but it was single track through recently mowed but still pretty high grass.

The first thirteen mile north along the feeder canal was a beautiful fun ride with good trail conditions, nice scenery, and a herons, turtles and jumping fish. We also saw very few other people on the ride. North of that and west of Lock 22 the trail was passable but less fun.

We ride hybrids with pretty wide tires. I'm not sure any of it would be fun on a road bike.

Hennepin Canal Parkway

Great Trail

August, 2017 by iembrdr4u

Nice easygoing trail for a newbie like me. Stayed at Hickory Grove Campground (great new owners) then early morning ride. Crushed stone & asphalt a little overgrown on the edges but a great trail

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