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Greenfield, WI Walking Trails and Maps

755 Reviews

Looking for the best Walking trails around Greenfield?

Find the top rated walking trails in Greenfield, 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
Surfaces
Type
59 Results
Activities
Length
Surfaces
Type

Almond Road Bike Path
1.5 mi
State: IL
Asphalt

Barstow to Frederick Street Connector (Route of the Badger)
0.9 mi
State: WI
Asphalt

Brown Deer Recreational Trail
1 mi
State: WI
Asphalt

Bugline Trail (Route of the Badger)

17.42 mi
State: WI
Asphalt

City of Franklin Hike and Bike Trail (Route of the Badger)
1.5 mi
State: WI
Asphalt

Des Plaines River Trail
56.1 mi
State: IL
Asphalt, Crushed Stone, Dirt, Gravel

Duck Lake Nature Area Trail
2 mi
State: WI
Dirt

Eisenbahn State Trail (Route of the Badger)

24.3 mi
State: WI
Asphalt, Crushed Stone

Glacial Drumlin State Trail (Route of the Badger)
53.2 mi
State: WI
Asphalt, Crushed Stone, Gravel

Glacial River Trail
55.8 mi
State: WI
Asphalt, Crushed Stone

Grant Woods Bike Path
5.9 mi
State: IL
Crushed Stone

Hank Aaron State Trail (Route of the Badger)
15.2 mi
State: WI
Asphalt, Crushed Stone

Hebron Trail
6.7 mi
State: IL
Crushed Stone, Gravel

Jefferson County Interurban Trail
2.25 mi
State: WI
Asphalt

KR Trail (Route of the Badger)
1.5 mi
State: WI
Asphalt, Boardwalk

Kenosha County Bike Trail (Route of the Badger)
7.9 mi
State: WI
Asphalt

Kenosha Pike Bike Trail (Route of the Badger)
6.95 mi
State: WI
Concrete

Lake Andrea Multi-Use Path
2.3 mi
State: WI
Asphalt

Lake to Lake Bike Trail
6.5 mi
State: WI
Crushed Stone, Gravel

Meadowbrook Trail (Route of the Badger)
2.4 mi
State: WI
Concrete
Accordion

Middlefork Savanna Trail

4.3 mi
State: IL
Crushed Stone, Gravel

Millennium Trail (IL)
30.7 mi
State: IL
Asphalt, Concrete, Crushed Stone

Milwaukee RiverWalk
3.1 mi
State: WI
Concrete

Moraine Hills State Park Trail
11.4 mi
State: IL
Asphalt, Crushed Stone

New Berlin Recreation Trail
7 mi
State: WI
Asphalt

Oak Leaf Trail (Route of the Badger)
123.6 mi
State: WI
Asphalt

Ozaukee Interurban Trail (Route of the Badger)
30.1 mi
State: WI
Asphalt

Pike River Pathway
6.9 mi
State: WI
Asphalt

Prairie Trail (IL)
26.4 mi
State: IL
Asphalt, Crushed Stone, Dirt, Gravel

White River State Trail (Route of the Badger)
19.7 mi
State: WI
Concrete, Crushed Stone, Gravel

Beerline Trail (Route of the Badger)
3.7 mi
State: WI
Asphalt

Chain O' Lakes Bike Path
3.2 mi
State: IL
Asphalt

Cushing Park Road Recreational Trail (Route of the Badger)
3 mi
State: WI
Asphalt

Fox River Trail (Route of the Badger)
6 mi
State: WI
Asphalt

Lake Country Trail
15.2 mi
State: WI
Asphalt

Lake Michigan Pathway (Route of the Badger)
14 mi
State: WI
Asphalt, Concrete, Crushed Stone

MRK Trail (Route of the Badger)

4.6 mi
State: WI
Crushed Stone

North Shore Bike Path
7.7 mi
State: IL
Asphalt, Crushed Stone

Pelishek-Tiffany Nature Trail
6 mi
State: WI
Dirt, Grass

Robert McClory Bike Path
25.4 mi
State: IL
Asphalt, Concrete, Crushed Stone

Root River Pathway (Route of the Badger)
6.6 mi
State: WI
Asphalt

Seven Waters Bike Trail (Route of the Badger)
18.6 mi
State: WI
Asphalt, Crushed Stone, Gravel

Sheboygan Interurban Trail
14 mi
State: WI
Asphalt

Skokie Valley Trail (Lake County)
9.8 mi
State: IL
Asphalt

Stone Mill Trail
1.5 mi
State: IL
Asphalt

West Allis Cross Town Connector (Route of the Badger)
0.9 mi
State: WI
Asphalt

Wild Goose State Trail
34.5 mi
State: WI
Asphalt, Crushed Stone, Dirt, Grass

Kinnickinnic River Trail (Route of the Badger)
2.3 mi
State: WI
Asphalt

Muskego Recreation Trail (Route of the Badger)
6.7 mi
State: WI
Crushed Stone, Dirt, Gravel

Powerline Trail (WI)
2.8 mi
State: WI
Asphalt

WE Energies Trail (Route of the Badger)
2 mi
State: WI
Asphalt, Gravel

Lake Geneva Bike Path (Route of the Badger)
8.9 mi
State: WI
Asphalt

Bull Valley Road Shared-Use Path
1.1 mi
State: IL
Asphalt

Fort Hill Bike Path
2.4 mi
State: IL
Asphalt

North Shore Trail (Route of the Badger)
3 mi
State: WI
Asphalt

Prairie Crossing Bike Path
3.7 mi
State: IL
Asphalt

Prairie Farms Trail
1.8 mi
State: WI
Crushed Stone, Dirt

Racine County Bike Trail (Route of the Badger)
1.4 mi
State: WI
Asphalt, Concrete

Racine-Sturtevant Trail (Route of the Badger)
3.5 mi
State: WI
Asphalt
Trail Image Trail Name States Length Surface Rating
This bike path sits on the east side of Almond Road between Washington Street and Fairfield Lane in Gurnee. The 8-foot wide asphalt path is used by residents as a spot for exercise and recreation, but...
 IL 1.5 mi Asphalt
The City of Waukesha has developed a number of connector trails to link popular trails and create continuous routes through the city. A number of longer, popular trails—such as the Glacial Drumlin...
 WI 0.9 mi Asphalt
The Brown Deer Recreational Trail runs through the Village of Brown Deer, a suburb of Milwaukee. The tree-line route parallels an active rail line through commercial and residential areas. Mid-way,...
 WI 1 mi Asphalt
Overview Broad blue skies strung with white cloud wisps; gem-green fields harboring cattails and butterflies; canopied glens giving way to cavernous quarries. It's all part of the ride on the...
 WI 17.42 mi Asphalt
The City of Franklin Hike and Bike Trail follows a corridor originally used by the Milwaukee Electric Railway & Light, an interurban railroad in southeastern Wisconsin. The corridor was later acquired...
 WI 1.5 mi Asphalt
Overview The Des Plaines River Trail runs alongside the Des Plaines River for just over 56 miles, protecting watershed habitat and forestland through much of Lake and Cook Counties. The trail is a...
 IL 56.1 mi Asphalt, Crushed Stone, Dirt, Gravel
The Duck Lake Nature Area Trail follows the southern side of Lake Como between Lake Geneva and Como, Wisconsin, not far from the Illinois state line. The trail is more rustic than most rail-trails and...
 WI 2 mi Dirt
Overview The Eisenbahn State Trail gives a nod to Wisconsin’s German heritage in its name—Eisenbahn is German for “railway.” The strict translation, “iron road,” refers to the iron rails originally...
 WI 24.3 mi Asphalt, Crushed Stone
Overview The 53-mile Glacial Drumlin State Trail between Cottage Grove and Waukesha provides a glimpse into the past when glaciers bore down on southeastern Wisconsin in the last Ice Age. Those...
 WI 53.2 mi Asphalt, Crushed Stone, Gravel
Overview The Glacial River Trail provides bikers, pedestrians, and in-line skaters with a 55.8-mile off-road/on-road rural route winding through farmland, prairie, wetlands, and woodlands as it...
 WI 55.8 mi Asphalt, Crushed Stone
About an hour northwest of Chicago, the beautiful Grant Woods Forest Preserve spans more than 1,000 acres, offering an outdoor respite of prairie, woodlands and marshes. The crushed limestone pathway...
 IL 5.9 mi Crushed Stone
In 1957, baseball legend Hank “The Hammer” Aaron led the Milwaukee Braves to the first of two consecutive World Series appearances and a championship over the usually dominant New York Yankees. In...
 WI 15.2 mi Asphalt, Crushed Stone
The Hebron Trail rolls across the northern Illinois prairie through the former corridor of the Kenosha and Rockford Railroad, known as the Kenosha Division Line at the time of its demise in 1939....
 IL 6.7 mi Crushed Stone, Gravel
The Jefferson County Interurban Trail is a paved multi-use trail that follows a former interurban rail line for what will eventually be almost eleven miles through Jefferson and Waukesha County. About...
 WI 2.25 mi Asphalt
The KR Trail is a new addition to Kenosha County’s growing bike-ped network. The trail picks up where the Kenosha Pike Bike Trail leaves off, in Petrifying Springs Park. From the northwest corner of...
 WI 1.5 mi Asphalt, Boardwalk
Overview The Kenosha County Bike Trail runs for nearly 8 miles in two sections separated by couple miles with the city of Kenosha. About the Route The northern segment runs between 1st St....
 WI 7.9 mi Asphalt
Helping to forge a connection between the northern and southern segments of the Kenosha County Bike Trail, the Kenosha Pike Bike Trail also has plenty to offer in its own right, giving trail users a...
 WI 6.95 mi Concrete
The 2.3-mile multiuse trail wraps around Lake Andrea in Pleasant Springs Park. The trail is an easy walk, run or ride around the lake, and is accessible for a wide range of users. It also helps users...
 WI 2.3 mi Asphalt
Overview The Lake to Lake Bike Trail winds through the beautiful terrain of the Kettle Moraine State Forest. It is a newer, well-maintained trail, with a wide, crushed limestone roadbed. It is used...
 WI 6.5 mi Crushed Stone, Gravel
Meadowbrook Trail parallels Meadowbrook Road offering a useful and convenient off-road route through northwest Waukesha. It begins at a connection to Lake Country Recreation Trail, a 15-mile east-west...
 WI 2.4 mi Concrete
Accordion
The Middlefork Savanna Forest Preserve is a natural gem hidden in an high-income neighborhood of Lake Forest, Illinois.  Those 600 acres are home to perhaps the best-preserved example of the rare...
 IL 4.3 mi Crushed Stone, Gravel
The Millennium Trail currently spans just over 30 miles in two disconnected segments, but there are plans to extend it to 35 miles and connect it to the Des Plaines River Trail. The trail goes through...
 IL 30.7 mi Asphalt, Concrete, Crushed Stone
The Milwaukee RiverWalk provides a pleasant way to get around Milwaukee from the Historic Third Ward, through downtown, and north to the Lower East Side. It also has easy connections to three other...
 WI 3.1 mi Concrete
Moraine Hills State Park Trail offers a wonderful experience for any geology or nature aficionado. A moraine is an accumulation of earth and stones carried and finally deposited by a glacier....
 IL 11.4 mi Asphalt, Crushed Stone
Overview The paved New Berlin Recreation Trail runs straight as an east-west compass bearing for 7 miles through the western Milwaukee suburbs, from New Berlin to Waukesha. While it is void of...
 WI 7 mi Asphalt
Overview The Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for 123 miles in and around the city of Milwaukee on a changing terrain of...
 WI 123.6 mi Asphalt
Overview If you’re going to visit the historical communities that lie just west of Lake Michigan, why not use the former route of the venerable interurban railroad? The Ozaukee Interurban Trail...
 WI 30.1 mi Asphalt
The Pike River Pathway is a paved, multiuse trail that parallels the river after which its named through meadows, fields, woods, and residential areas in the Village of Mount Pleasant, WI.  From...
 WI 6.9 mi Asphalt
Overview The Prairie Trail runs the length of McHenry County and is managed by the McHenry County Conservation District. The rail trail spans just over 26 miles from the Wisconsin border and the...
 IL 26.4 mi Asphalt, Crushed Stone, Dirt, Gravel
Overview The White River State Trail is a 19.7-mile trail composed of two separate segments: a 12-mile stretch that runs between Elkhorn and just west of Burlington in Walworth County, and a 7-mile...
 WI 19.7 mi Concrete, Crushed Stone, Gravel
Overview The Beerline Trail, named after the corridor that was once used by freight trains transporting the ingredients for beer to some of Milwaukee’s famous breweries, runs for 3.7 miles through...
 WI 3.7 mi Asphalt
The Chain O' Lakes Bike Path is a paved trail that runs between E. Grand Avenue in Fox Lake and Grant Woods Forest Preserve to the east. The trail parallels the railroad track and Rollins Road/CR 31,...
 IL 3.2 mi Asphalt
The Cushing Park Road Recreational Trail begins on the western outskirts of Delafield, a small community about 30 miles west of Milwaukee. From Delafield's Main Street, the trail heads south,...
 WI 3 mi Asphalt
The Fox River Trail runs diagonally along its namesake waterway through Waukesha in southeastern Wisconsin (just outside of Milwaukee). A trailhead at the E.B. Shurts Environmental Education Center in...
 WI 6 mi Asphalt
Overview The 15.2-mile Lake Country Trail runs from the western edge of Waukesha to Oconomowoc in Wisconsin’s Lake Country area. Most of the trail was built on a former Milwaukee-Watertown...
 WI 15.2 mi Asphalt
The 13.5-mile Lake Michigan Pathway keeps you in close touch with the sixth-largest freshwater lake in the world as it links rail-trails north and south of the port city of Racine. Along the way, the...
 WI 14 mi Asphalt, Concrete, Crushed Stone
Racine County's eastern edge is home to the MRK Trail, a rail-with-trail that extends north from the City of Racine to the Village of Caledonia. Because Racine County standardized its signs several...
 WI 4.6 mi Crushed Stone
The North Shore Bike Path runs for nearly 8 miles between Lake Bluff and Mundelein, paralleling State Route 176 for the path's entire length. The trail is one of dozens in the Chicagoland area, all of...
 IL 7.7 mi Asphalt, 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
Overview The Robert McClory Bike Path runs the length of Lake County, knitting together a string of communities on the north shore of Chicago all the way to the Wisconsin border. In 1997, the trail...
 IL 25.4 mi Asphalt, Concrete, Crushed Stone
The Root River Pathway uses a combination of off-road trail and on-road route to form a crescent around the City of Racine. The trail closely follows the bends of the Root River, making it a great...
 WI 6.6 mi Asphalt
Overview The Seven Waters Bike Trail is a scenic corridor stretching more than 18 miles north–south between Burlington and Muskego Lake into Waukesha County. The trail was originally three trails,...
 WI 18.6 mi Asphalt, Crushed Stone, Gravel
The Sheboygan Interurban Trail follows the route of an electric railway that once ran between Milwaukee and Sheboygan from the early 1900s to 1951. The trail begins at Pebble Beach Road on the Ozaukee...
 WI 14 mi Asphalt
Overview The Skokie Valley Trail connects Highland Park in the south to the northern trailhead in Lake Bluff. The entire trail corridor is a rail-with-trail, paralleled by double tracks that sit...
 IL 9.8 mi Asphalt
The Stone Mill Trail runs between Lawrence Road in Harvard and Maxon Road in Chemung. The 1.5-mile, paved trail mostly parallels County Highway 17 (Ramer Road) and active railroad tracks, and will...
 IL 1.5 mi Asphalt
Although short, the West Allis Cross Town Connector represents an important start to a future link between three trails in Milwaukee County. Currently, the trail begins at a junction with the New...
 WI 0.9 mi Asphalt
Closure Notice: The Wild Goose State Trail is currently closed between Prospect Rd. and Teal Rd. Please check with Wisconsin DNR for more current information. The Wild Goose State Trail is a...
 WI 34.5 mi Asphalt, Crushed Stone, Dirt, Grass
Kinnickinnic River Trail (called the KK River Trail by locals) runs just over 2 miles in southern Milwaukee, following the river through a densely populated and industrial corridor. The trail links...
 WI 2.3 mi Asphalt
The Muskego Recreation Trail follows a corridor originally used by the Milwaukee Electric Railway & Light, an interurban railroad in southeastern Wisconsin. The corridor was later acquired by...
 WI 6.7 mi Crushed Stone, Dirt, Gravel
Stretching east-west through the City of Greenfield, the Powerline Trail is a new shared-use path that offers multiple recreation and transportation opportunities for locals and visitors alike. The...
 WI 2.8 mi Asphalt
The WE Energies Trail, so named because it uses a Wisconsin Energy Corporation utility corridor for much of its route, links Racine and Oak Creek in Racine and Milwaukee counties. Despite the presence...
 WI 2 mi Asphalt, Gravel
Overview The 8.9-mile Lake Geneva Bike Path runs through the scenic resort city, offering connections to many of the community’s amenities. The trail has five unique, color-coded segments. About...
 WI 8.9 mi Asphalt
The Bull Valley Road Shared-Use Path travels along the south side of Bull Valley Road in the city of McHenry, Illinois. The paved path is suitable for non-motorized uses including walking, jogging,...
 IL 1.1 mi Asphalt
The Fort Hill Bike Path trail sits on the north side of Peterson Road/ County Road 20. The trail peels away from the Prairie Crossing Bike Path at Midlothian Road and extends west, passing industries...
 IL 2.4 mi Asphalt
Racine’s southeastern neighborhoods are home to the North Shore Trail, which extends south to the Racine–Kenosha county line. Because Racine County standardized its signs several years ago, you won't...
 WI 3 mi Asphalt
The Prairie Crossing Bike Path is a hard surface trail connecting Mundelein to Grayslake in central Lake County, Illinois. The trail is perpendicular to the 30-plus-mile Millennium Trail, which it...
 IL 3.7 mi Asphalt
With farmland to the east and the Des Plaines River Floodplain to the west, this picturesque trail is a relaxing adventure on two feet or on wheels. The crushed stone trail runs from Prairie Springs...
 WI 1.8 mi Crushed Stone, Dirt
Helping to extend the excellent network of trails around the city of Racine deeper west into the heart of the county, the Racine County Bike Trail serves as a disconnected addition to the...
 WI 1.4 mi Asphalt, Concrete
The Racine-Sturtevant Trail runs for 3.5 miles from the western side of Racine to near the eastern edge of the Village of Sturtevant. The trail occupies an abandoned rail corridor for most of its...
 WI 3.5 mi Asphalt

Recent Trail Reviews

Lake to Lake Bike Trail

The trail is well maintained and an easy ride. It follows the terrain. The views are beautiful. Lots of families either walking or biking.

June, 2025 by jsahmblnd

The trail is well maintained and an easy ride. It follows the terrain. The views are beautiful. Lots of families either walking or biking.

read more …

Des Plaines River Trail

very confusing

June, 2025 by mrjocasio

I did this trail on bike 2 years ago and I hated it, signage is terrible, at one point after Golf road, you literally come to an end and have to carry your bike over train tracks and active train tracks. No signs of any sort. You go through a campground that confuses you even more. I won’t do it again. To ridiculous.

read more …

Wild Goose State Trail

Since the tornado in May 2025 there is two miles of trees down not far from Juneau. It is impassable. I rerouted from prospect onto Hwy 26 to Swan Rd.

June, 2025 by alloy_smile

Since the tornado in May 2025 there is two miles of trees down not far from Juneau. It is impassable. I rerouted from prospect onto Hwy 26 to Swan Rd.

read more …
Accordion

Fox River Trail (Route of the Badger)

I enjoyed the south half but the part through the city was not well or marked at all. Route would be vastly improved with some signage.

June, 2025 by jmperl63

I enjoyed the south half but the part through the city was not well or marked at all. Route would be vastly improved with some signage.

read more …

Powerline Trail (WI)

Unleashed Dogs

June, 2025 by stevet53220

Dogs run free on Phase 1 trail.

read more …

Sheboygan Interurban Trail

not a “trail”

May, 2025 by r99ghs5zhr

Started at the depot in Oostburg and headed north. After a few blocks we re-checked the app and saw it was just a bike *route*, not really a trail. We turned around and went back. No idea why this is considered a trail. It’s just a bike route. I don’t mind sharing with cars for short sections but I don’t consider riding busy country roads for miles worthy of “trail” designation.

read more …

Prairie Trail (IL)

electric assist needed

May, 2025 by danwarwick

Started in McHenry and went south. Did 33 miles round trip. McHenry to Crystal Lake lots of ruts and bumpy. Just north of Crystal Lake becomes a new, very smooth trail, but is extremely hilly with lots of turns. After going through a small section of downtown Crystal Lake becomes not as hilly to Algonquin.

read more …

White River State Trail (Route of the Badger)

Great Trail

May, 2025 by johnryan041985

Can confirm that many lazy and inconsiderate dog owners leave their dog's poops right on the trail, so keep an eye out for landmnes. Also beware that many people do not have their dogs on leashes, so have protection on you and stay vigilant. Beautiful farmland scenery starting from the Vandenboom trailhead heading west. Very flat, and occasional holes in trail possibly from critters. Nice that each road you reach from the trailhead is just about 1 mile so it's easy to gauge the distance you've walked.

read more …

Prairie Trail (IL)

Navigation thru Crystal Lake an climbs in Sterne's Woods

April, 2025 by tabuffa

Late April Sunday in clear weather. Started at southern end as marked on Traillink map. There is no dedicated parking but on-street parking in surrounding residential neighborhood was without issues. Rode north to McHenry, 16 miles. Surface is newly or recently repaved and excellent, until you reach Pleasant Hill Road, then only fair, with expansion cracks every 50 60 feet, bumpy ride into McHenry but very doable. Generally pleasant, only partially shaded ride, but not the most picturesque.
2 issues around Crystal Lake, first, signage for on-road traverse of the town is inadequate in both directions. Going north, 2 blocks after crossing the railroad tracks, you have to jog East from Main Street 3 blocks to Glen Ave., then cross IL 176 onto Lorraine Dr. to reach the continuation of the trail into Sterne's Woods. Visa versa coming south. Second, be aware there are several short but steep climbs and descents going through Sterne's Woods. Seamless continuation onto Fox River trail at southern end.

read more …

Wild Goose State Trail

Lovely Trail

November, 2024 by the_masseuse

It’s pretty scenic, especially with the leaf colors. Also pretty busy! There’s parking on both ends. A lot of the trail is grass, not even gravel. The spot where it’s asphalt is very minimal. It’s awesome you can stop and ride through Horicon Marsh! Lots of kitties on this trail ¿

read more …

Jefferson County Interurban Trail

stunning and peaceful

October, 2024 by wilsonae

Just kept riding. Gorgeous fall day. Started at northern trailhead. Passed a few walkers and one other biker the whole way to the end. As noted it has been extended well past 2.2 miles. Lovely scenery and immaculate trail surface with lots of peaceful farms. My new fave!

read more …

Glacial Drumlin State Trail (Route of the Badger)

Great trail, but there's a temporary closure

October, 2024 by sarahccaltvedt

We rode about 23 miles round-trip from the Waukesha trailhead on Oct. 12. The asphalt is in pretty good condition, with just a few bumps. However, when we got to the big curve around what used to be a field east of Dousman, we discovered that the field is now a massive construction site, and the trail is closed indefinitely, with no posted detour. We don't take our tandem on roads, so we turned around at that point. I assume that the trail is open west of the construction site, but don't know exactly where.

We didn't ride on the western portion of the trail that day, but it's one of our favorites, especially the part where you bike across the lake.

read more …
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Explore by Activity

ATV
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Running
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