Boscobel, WI Hike Trails and Maps

388 Reviews

Looking for the best Hike trails around Boscobel?

Find the top rated hike trails in Boscobel, whether you're looking for an easy short hike trail or a long hike trail, you'll find what you're looking for. Click on a hike 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

Old Highway 131 Trail

5.7 mi
State: WI
Asphalt, Boardwalk, Crushed Stone

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
Accordion

Paint Creek Trail (IA)

2.5 mi
State: IA
Dirt

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

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
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 and St....
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. Three hand-dug tunnels along the Elroy-Sparta State Trail make utter darkness as much a part of the scenery as rolling...
WI 33.8 mi Crushed Stone
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 Railroad, the...
WI 11.2 mi Asphalt
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 passes through...
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
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 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
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 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
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 formations, some...
WI 12 mi Asphalt, Gravel
Accordion
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
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
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

400 State Trail

LaValle to Elroy bridges in harsh shape

September, 2025 by julieganser

We rode this stretch out and back on September 15, 2025. The trail is flat and in good shape except for the numerous bridges (10 or 12) which are in pretty bad shape. It’s obvious that a few repairs were recently attempted, but those amount to replacement of a few boards in each bridge. Some bridges are very long and all are super bumpy. If you have an older bike I’d suggest walking it across the longer bridges. Otherwise the scenery is nice and there’s great rest areas with flush toilets in LaValle, Wonewoc and Elroy.

Elroy-Sparta State Trail

Second long trip for me and the first trip that was mostly rail trail one quarter of which was the Elroy Sparta. Beautiful trail and the safety of being away from most automobile traffic made the trip way less stressful

September, 2025 by warpony1929

Second long trip for me and the first trip that was mostly rail trail one quarter of which was the Elroy Sparta. Beautiful trail and the safety of being away from most automobile traffic made the trip way less stressful

Elroy-Sparta State Trail

Nostalgia Trip

August, 2025 by malia.bergstrom

We rode Sparta to Norwalk, through tunnel 3. Two of our group had ridden the entire length in the early 70s, so it was a nostalgic day. They recalled seeing farmland and we saw a little of that, but trees have grown up and it’s mainly a nice, shaded, flat ride.

Accordion

Great Sauk State Trail

super smooth

August, 2025 by julieganser

Rode this trail end-to-end yesterday. The asphalt is in like-new condition and the scenery is beautiful. While we greatly prefer shaded trails in the hot summer, the lengthy stretches of sun on this trail were tolerable due to temps in the high 70’s and a light breeze. Can’t wait to ride this again in the fall. I’m sure the autumn colors near the northern half will be spectacular.

400 State Trail

Trail is flat, mostly shaded, and well maintained. Bridge crossings often rough/bumpy due to repairs to damage from snowmobiles. (Thus 4 stars not 5)Legion Park in Wonewock is a great place to camp plus it is an interesting historic town.

August, 2025 by skiyaker

Trail is flat, mostly shaded, and well maintained. Bridge crossings often rough/bumpy due to repairs to damage from snowmobiles. (Thus 4 stars not 5)Legion Park in Wonewock is a great place to camp plus it is an interesting historic town.

Elroy-Sparta State Trail

3.5 at best

August, 2025 by bonafire86

A 5 star is really stretching this. I get the history of this being the 1st rail to trail and the cool tunnels, but the very narrow gravel path is not much to desire. The landscape doesn’t change much and the overgrown weeds and trees prevent much scenery. Occasional stream is a welcome sight on this boring path. America’s bicycle capital is needing a little update to encourage us to return. Glad we had headlamps for the almost two mile long tunnel raining on us. Riding, rather than walking was our choice to speed it up but if you’re not steady - then walk.

Elroy-Sparta State Trail

good tunnels

July, 2025 by dominick.nocchi

The tunnels on the trail are nice, cool bluffs and overall very nice trail

Omaha Trail

Oh, Omaha

June, 2025 by muzzikdir1

We ride trails. We love trails. No pavement required. We embrace the crushed surface. We love to bike. The Omaha trail is surrounded by beautiful scenery. It begins and ends in friendly towns. It was strewn with debris the day after a storm, yet we were undeterred. You can bike around debris. Sadly, you can’t miss the ridges, ruts and roughness of a once paved trail. Omaha stole our energy and joy of riding. We rode on because we don’t quit. But it wasn’t enjoyable and was only memorable for the relief of finishing and knowing we won’t ride Omaha again. It’s unfortunate. The 400 is nearby. It is a far better choice, as is just about any other trail.

400 State Trail

Great trail!

June, 2025 by christyfry14

Rode the trail the last couple days, loved it. It’s in great shape and is pretty flat. Happened to be there when the Wheelmen were riding with the high wheels!

Old Highway 131 Trail

Pretty ride

June, 2025 by syq888wxgy

Quick ride and beautiful views.

Great Sauk State Trail

Rode out 6+ miles from the south end. Apparently they are going to build a bridge across the river sometime soon..Noticed a sign along the trail, that stated you need a permit to ride the trail?! Nice along the river, then out into open fields.

June, 2025 by rickseconds1961

Rode out 6+ miles from the south end. Apparently they are going to build a bridge across the river sometime soon..Noticed a sign along the trail, that stated you need a permit to ride the trail?! Nice along the river, then out into open fields.

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

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