Boscobel, WI Walking Trails and Maps

377 Reviews

Looking for the best Walking trails around Boscobel?

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

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Activities
Length
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Type
27 Results
Activities
Length
Surfaces
Type

400 State Trail

21.9 mi
State: WI
Crushed Stone

Alliant Powerline Trail

0.7 mi
State: IA
Asphalt

Bee Branch Trail

1.56 mi
State: IA
Asphalt, Concrete

Bergfeld Recreation Trail

1.8 mi
State: IA
Asphalt

Dubuque Jaycees Trail

1.28 mi
State: IA
Asphalt

Elroy-Sparta State Trail

33.8 mi
State: WI
Crushed Stone

Great Sauk State Trail

11.2 mi
State: WI
Asphalt

Heritage Trail (IA)

29.2 mi
State: IA
Asphalt, Crushed Stone

Mississippi Riverwalk Trail

0.95 mi
State: IA
Concrete

Pammel Creek Trail

2 mi
State: WI
Asphalt

Pony Hollow Trail

3.6 mi
State: IA
Crushed Stone, Dirt, Grass

Rountree Branch Trail

3 mi
State: WI
Asphalt, Concrete

Southern Levy Trail

0.7 mi
State: IA
Asphalt

Wolf Run Trail (WI)

2 mi
State: WI
Crushed Stone

Cheese Country Recreation Trail

46.4 mi
State: WI
Crushed Stone, Dirt, Gravel

Hillsboro State Trail

4.3 mi
State: WI
Crushed Stone, Gravel

Military Ridge State Trail

40 mi
State: WI
Asphalt, Crushed Stone

Northwest Arterial Trail

4.8 mi
State: IA
Asphalt

Omaha Trail

12 mi
State: WI
Asphalt, Gravel

Paint Creek Trail (IA)

2.5 mi
State: IA
Dirt
Accordion

Pecatonica State Trail

10 mi
State: WI
Crushed Stone

Pine River Trail

14.3 mi
State: WI
Boardwalk, Crushed Stone, Dirt, Grass

Forest Hills Trail

1.5 mi
State: IA
Asphalt, Concrete

Old Highway 131 Trail

5.7 mi
State: WI
Asphalt, Boardwalk, Crushed Stone

Sanders Creek Trail

1.1 mi
State: WI
Concrete

Trolley Line Trail (IA)

0.57 mi
State: IA
Asphalt, Concrete

Wisconsin River Trail

0.4 mi
State: WI
Concrete
Trail Image Trail Name States Length Surface Rating
Overview Traveling the 400 State Trail is a numbers game. The trail’s name refers to the old Chicago and North Western Railway’s “No. 400” passenger train that zoomed through here between Chicago...
WI 21.9 mi Crushed Stone
A short trail that makes creative use of a utility corridor on the southeastern bluffs of Dubuque, the Alliant Powerline Trail provides a paved, tree-lined path perfect for dog-walking or exercising -...
IA 0.7 mi Asphalt
The Bee Branch Trail system forms an important connection between the almost thirty-mile Heritage Trail (IA), the crown jewel of the area's trails, and the Mississippi River and Chaplain Schmitt...
IA 1.56 mi Asphalt, Concrete
Nestled amidst the suburban landscape on the western outskirts of Dubuque, the Bergfeld Recreation Area is a 30-acre park with playgrounds, fishing spots on the Bergfeld Pond, and the Bergfeld...
IA 1.8 mi Asphalt
The Dubuque Jaycees Trail runs for just over a mile from Pyatigorsk Park (named for a Russian sister city to Dubuque) up to the 8-acre A.Y. McDonald Park, a popular fishing and boat launch spot...
IA 1.28 mi Asphalt
Note: The three tunnels on the trail close from Nov. 1 to April 30 each year. Overview Three hand-dug tunnels along the Elroy-Sparta State Trail make utter darkness as much a part of the scenery...
WI 33.8 mi Crushed Stone
Overview The Great Sauk State Trail spans nearly a dozen miles connecting the communities of Sauk City, Prairie du Sac, and Merrimac.  About the Route Built along the former Union Pacific...
WI 11.2 mi Asphalt
Overview The Heritage Trail rolls along like a dream for nearly 30 miles from the Mississippi River town of Dubuque to Dyersville, home of the movie set for Field of Dreams. Along the way, it...
IA 29.2 mi Asphalt, Crushed Stone
A spacious path easily identifiable by it's red-patterned concrete, the Mississippi Riverwalk Trail runs just under a mile along the river, connecting some of Dubuque's major tourist attractions and...
IA 0.95 mi Concrete
The Pammel Creek Trail is a paved path in La Crosse. The trail mostly follows the alignment of the Pammel Creek channel. The trail travels through residential areas in the south part of La Crosse,...
WI 2 mi Asphalt
The Pony Hollow Trail in the northeastern Iowa city of Elkader offers a scenic route through woodlands and wetlands along the former Chicago, Milwaukee and St. Paul Railroad bed. The western half of...
IA 3.6 mi Crushed Stone, Dirt, Grass
The Rountree Branch Trail begins where Chestnut Street in Platteville crosses the Rountree Branch stream and continues 2.7 miles to Keystone Parkway. The trail connects trails on the UW-Platteville...
WI 3 mi Asphalt, Concrete
An asphalt path lined with cracks and sprouting grass, the Southern Levy Trail might not be much to look at itself, and its route limits its usefulness as anything but an out-and-back recreational...
IA 0.7 mi Asphalt
The Wolf Run Trail supports a wide variety of users on its two miles of crushed gravel, situated on the outskirts of Mazomanie in northwestern Dane County. Heading southeast from the charming...
WI 2 mi Crushed Stone
Overview    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...
WI 46.4 mi Crushed Stone, Dirt, Gravel
The 4.3-mile Hillsboro State Trail will make you feel instantly at home. Starting out easy with a crushed stone surface before turning to slightly more difficult loose gravel, this trail will take you...
WI 4.3 mi Crushed Stone, Gravel
NOTE: A State Trail Pass ($25 annually/$5 daily) is required for bicyclists and in-line skaters ages 16 and older. Snowmobilers must display either a Wisconsin registration or a snowmobile State Trail...
WI 40 mi Asphalt, Crushed Stone
Providing over four and a half miles of smooth asphalt trail, perfect for commuting or recreation, the Northwest Arterial Trail helps adds off-road connectivity to Dubuque's western suburbs and also...
IA 4.8 mi Asphalt
Overview The 12-mile Omaha Trail passes through a wonderland of towering buttes, mesas, and pinnacles that seem more at home in an arid desert than in fertile farmland. The steep sandstone...
WI 12 mi Asphalt, Gravel
Iowa's Yellow River State Forest contains a sprawling network of hiking, equestrian and bicycle trails. The Paint Creek Trail, which occupies a segment of an abandoned railroad corridor, is the only...
IA 2.5 mi Dirt
Accordion
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 Pine River Trail winds on an abandoned railroad corridor between Richland Center and Lone Rock in scenic Richland County. Trail users are treated to stunning views of river bluffs, marshland and...
WI 14.3 mi Boardwalk, Crushed Stone, Dirt, Grass
The Forest Hills Trail is a nice multi-use recreation trail that forms a circuit around a subdivision in the city of Asbury, just west of Dubuque. Perfect for walking, jogging, and other forms of...
IA 1.5 mi Asphalt, Concrete
Situated in the heart of the Driftless Region, the Old Highway 131 trail holds both cultural, geological and historical significance. Even before the old highway was established, the Ho-Chunk nation...
WI 5.7 mi Asphalt, Boardwalk, Crushed Stone
The Sanders Creek Trail begins on the north end of Boscobel and winds southward through town along its namesake creek. The paved pathway offers a pleasant experience in a greenspace bordering quiet...
WI 1.1 mi Concrete
Built on the same route that a streetcar once used to carry passengers to the impressive overlooks of Eagle Point Park, the half-mile long Trolley Line Trail provides a convenient and scenic means of...
IA 0.57 mi Asphalt, Concrete
The Wisconsin River Trail is a developing pathway which will one day connect the communities of Boscobel, Woodman, and Wauzeka in southwestern Wisconsin. The loop trail will be built in four phases...
WI 0.4 mi Concrete

Recent Trail Reviews

Great Sauk State Trail

Smooth

March, 2025 by zqbh6swvsm

Super nice trail! I think I counted 2 cracks. Well marked. Feel free to ride your road bike. Parked on the north end. There are about five parking spots there. Only downside is that it’s quite open which can expose you to wind

Great Sauk State Trail

March 18, 2025 Ride

March, 2025 by djones223

Almost spring, mild 60 deg. F sunny day, good day for a bike ride. I started at Bill Fuchs Park, plenty of parking, and rode 12.5 miles to the end of the Great Sauk State Trail via the riverfront for the first third of the trail and then joined up with the Great Sauk trail for the last two thirds of the ride out. The trail is paved and very smooth, with hardly any expansion joints or cracks.
The first part of my ride was a mix of great views of the Wisconsin River and river bottom woods. The trail wound through farm fields and grasslands after leaving the river onto the plains.

Great Sauk State Trail

I have ridden this trail a couple of times and have enjoyed the trail quality and the river and prairie scenery. The only complaint I have is that the trail ends before getting into Devils Lake State Park which could make the trail spectacular.

October, 2024 by mankato

I have ridden this trail a couple of times and have enjoyed the trail quality and the river and prairie scenery. The only complaint I have is that the trail ends before getting into Devils Lake State Park which could make the trail spectacular.

Accordion

Heritage Trail (IA)

Best trail I’ve seen this year

October, 2024 by brownlincolnt

Absolutely gorgeous ride with the trail in perfect condition. Unlike other trails, this one is serviced often with repairs being done with crushed gravel instead of sand. They have put multiple new bathroom facilities throughout the trail as well.

400 State Trail

We will return to the 400

September, 2024 by ellaqk_tl

We had ridden into Elroy from Sparta and realized the 400 trail left from there. We went back to Elroy two days later and rode 11 miles out on the 400. We went through Union and through Wonewoc. We were so impressed with the little town of Wonewoc and the super clean facility they had along the trail, that included a picnic shelter and water fountain along with bike repair stands. The ride itself was very nice. The trail was well cared for and there were many bridges that overlooked very pretty areas. We passed several large rock formations that were impressive. We hope to return to the area so we can ride the entire trail.

400 State Trail

We will return to the 400

September, 2024 by ellaqk_tl

We had ridden into Elroy from Sparta and realized the 400 trail left from there. We went back to Elroy two days later and rode 11 miles out on the 400. We went through Union and through Wonewoc. We were so impressed with the little town of Wonewoc and the super clean facility they had along the trail, that included a picnic shelter and water fountain along with bike repair stands. The ride itself was very nice. The trail was well cared for and there were many bridges that overlooked very pretty areas. We passed several large rock formations that were impressive. We hope to return to the area so we can ride the entire trail.

Elroy-Sparta State Trail

Sparta to Elroy

September, 2024 by ellaqk_tl

For years, we talked about riding the Elroy to Sparta trail and this summer we finally did it. We were to ride 1/2 of the trail from Sparta towards Elroy and then were going to ride the other 1/2 of the trail from Elroy towards Sparta the following day. However, one of the friends we were going to ride with became ill and my husband and I decided we would go ahead and get part of the ride in. Part way through my husband decided we would ride the whole trail in one day. We entered the first tunnel which required us to walk our bikes, wear our raincoats and use a light. It was very cool. The floor of the tunnel was wet and slippery and before even entering the tunnel I found myself with soaking wet shoes but they dried fast. We stopped just a little further east of the tunnel to use restroom facilities which were clean. On we went into Wilton, which I have to say we were rather unimpressed with. The toilet facility was sorely lacking in cleanliness and we found a picnic table that was none too clean either. We continued on to Elroy and surprisingly I was able to find an Uber ride back to Sparta to pick up our truck with no time to spare as a terrible storm rolled through. Fortunately for my husband, who was waiting for me, was able to find shelter in Elroy at their welcome center. We had brought along with us shower essentials and clean clothes and were able to shower in Elroy. It is free but they do suggest a donation which we were more than happy to do. Some of the highlights were the three tunnels and the remaining overhead structure that had wires that would hang from it to alert those on the top of the train (Hobos and brakeman) the tunnel was ahead. Also, we had a large buck come up onto the trail who did not know we were there. He stood there in all his beauty until he caught sight of us and quickly disappeared into the brush. Overall, I would highly recommend this trail ride. We may do it again.

Great Sauk State Trail

awesome relaxing ride

September, 2024 by 49zhs7nbgx

It’s a well maintained, paved trail with markers and sculptures along the way. The scenery is beautiful!!

Northwest Arterial Trail

Decent trail

September, 2024 by dpate

I rode the Northwest Arterial Trail on a chilly day in early September. It’s a nice paved trail that runs beside the NW Arterial Road so it’s a bit noisy and there are a few death machine crossings. It’s nice that it connects to the Heritage Trail in the north. I also found some Iowa hills! I give this one four stars for highway noise. Traveling cyclist Facebook

Heritage Trail (IA)

Fabulous trail

August, 2024 by dpate

I rode this trail over three days on ten mile out and back trips in perfect weather starting in Dubuque to Durango, then next day to Epworth, then on to Dyersville. I normally try to ride paved trails but this one was a pleasant surprise. The crushed stone is like cement and I could ride 18 MPH easily with no issue. It was very scenic and mostly shaded with no big hills. Even the recent rain on day two did not seem to affect it. I rate this one high! This is the epitome of a great gravel trail. 5 stars. Traveling cyclist Facebook

Bee Branch Trail

Nice little trail

August, 2024 by dpate

I happened upon this trail as I was riding the Heritage Trail that it connects to. Very enjoyable and beautiful trail. Great spot for the locals. 5 stars from me.. Traveling Cyclist Facebook

Paint Creek Trail (IA)

Nice wooded trail

August, 2024 by xgqrms2jbn

The Paint Creek trail is short but very enjoyable. At some point a tracked vehicle was on the trail when it was soft and left some track stutter bumps that reduced my enjoyment. There was a short repaired section that had large loose rocks. I started on the west side but I could not completely finish the trail because it was flooded toward the east end. I give it 4 stars only for the manmade stutter bumps.
Traveling cyclist
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