Oconomowoc, WI Running Trails and Maps

721 Reviews

Looking for the best Running trails around Oconomowoc?

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

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Activities
Length
Surfaces
Type
75 Results
Activities
Length
Surfaces
Type

Brown Deer Recreational Trail

1 mi
State: WI
Asphalt

Bugline Trail (Route of the Badger)

17.42 mi
State: WI
Asphalt

Cannonball Path

3.9 mi
State: WI
Asphalt

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

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

Kiwanis Bike Trail

4 mi
State: WI
Asphalt

Lake to Lake Bike Trail

6.5 mi
State: WI
Crushed Stone, Gravel

Lower Yahara River Trail

2.5 mi
State: WI
Asphalt, Boardwalk

Mascoutin Valley State Trail

21 mi
State: WI
Crushed Stone, Grass, Gravel
Accordion

Milwaukee RiverWalk

3.1 mi
State: WI
Concrete

New Berlin Recreation Trail

7 mi
State: WI
Asphalt

Oak Leaf Trail (Route of the Badger)

123.6 mi
State: WI
Asphalt

Peace Trail

6.4 mi
State: WI
Asphalt

Pheasant Branch Conservancy Trail

4.2 mi
State: WI
Crushed Stone

Pike River Pathway

6.9 mi
State: WI
Asphalt

Prairie Trail (IL)

26.4 mi
State: IL
Asphalt, Crushed Stone, Dirt, Gravel

Rock River Parkway Trail

2.4 mi
State: WI
Asphalt, Concrete

Sheboygan Interurban Trail

14 mi
State: WI
Asphalt

Southwest Commuter Path

5.6 mi
State: WI
Asphalt

Spring Brook Trail

5.1 mi
State: WI
Asphalt

Upper Yahara River Trail

2.9 mi
State: WI
Asphalt, Boardwalk

White River State Trail (Route of the Badger)

19.7 mi
State: WI
Concrete, Crushed Stone, Gravel

Badger State Trail

39.8 mi
State: WI
Asphalt, Crushed Stone

Capital City State Trail

17.2 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

Long Prairie Trail

13.9 mi
State: IL
Asphalt, Crushed Stone

MRK Trail (Route of the Badger)

4.6 mi
State: WI
Crushed Stone

Military Ridge State Trail

40 mi
State: WI
Asphalt, Crushed Stone

Muskego Recreation Trail (Route of the Badger)

6.7 mi
State: WI
Crushed Stone, Dirt, Gravel

North Mendota Trail

4.14 mi
State: WI
Asphalt, Boardwalk

Old Plank Road Trail (WI)

37.6 mi
State: WI
Asphalt

Peebles Trail

5.6 mi
State: WI
Asphalt

Pelishek-Tiffany Nature Trail

6 mi
State: WI
Dirt, Grass

Prairie Trail (WI)

6.7 mi
State: WI
Asphalt

Seven Waters Bike Trail (Route of the Badger)

18.6 mi
State: WI
Asphalt, Crushed Stone, Gravel

Stone Mill Trail

1.5 mi
State: IL
Asphalt

Wild Goose State Trail

34.5 mi
State: WI
Asphalt, Crushed Stone, Dirt, Grass

Starkweather Creek Path

3.1 mi
State: WI
Asphalt

WE Energies Trail (Route of the Badger)

2 mi
State: WI
Asphalt, Gravel

Blackhawk Path

2.3 mi
State: WI
Asphalt

Brooke Street Trail

2 mi
State: WI
Asphalt

CamRock Trail

2.4 mi
State: WI
Crushed Stone

Downtown Trail (WI)

1 mi
State: WI
Asphalt, Crushed Stone

Harbor View Trail

1.1 mi
State: WI
Asphalt

Lake Andrea Multi-Use Path

2.3 mi
State: WI
Asphalt

Powerline Trail (WI)

2.8 mi
State: WI
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

Riverside Corridor Bike-Walking Trail

9.2 mi
State: WI
Asphalt, Concrete

South Connector Trail

3.8 mi
State: WI
Asphalt

Wingra Creek Path

1.9 mi
State: WI
Asphalt

Yahara River Bike Path

0.9 mi
State: WI
Asphalt
Trail Image Trail Name States Length Surface Rating
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 Cannonball Path runs on a railbanked Union Pacific corridor from near downtown Madison to Fitchburg, a southern suburb. A majority of the paved trail is complete between Madison's...
WI 3.9 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
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
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 passes through...
WI 55.8 mi Asphalt, 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 Kiwanis Bike Trail, named for the Kiwanis Club that spearheaded the effort to build the trail, parallels the western bank of the Rock River through the southern Wisconsin community of Janesville....
WI 4 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
Dane County's Lower Yahara River Trail offers an incredibly scenic experience in the Madison area. On its western end, the 2.5-mile paved pathway connects to the Capital City State Trail near the...
WI 2.5 mi Asphalt, Boardwalk
The Mascoutin Valley State Trail is divided into two segments along a former corridor of the Chicago and North Western Railway. The eastern section runs 10 miles between Fond du Lac and Rosendale. The...
WI 21 mi Crushed Stone, Grass, 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 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
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
Stretching from Afton to Janesville, the Peace Trail offers a paved, tree-shaded route paralleling the Rock River and an active rail line. From its northern end in Janesville, the trail crosses the...
WI 6.4 mi Asphalt
The Pheasant Branch Conservancy Trail forms a loop within the scenic Pheasant Branch Conservancy, a natural area containing a marsh, meadows, forest and hills. The area is home to a vast array of...
WI 4.2 mi Crushed Stone
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
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
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
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
All it takes is a short ride on Madison’s 5.6-mile South  west Commuter Path to understand the critical role it plays in getting people around town. Not only does it pass within a mile of the State...
WI 5.6 mi Asphalt
Janesville's Spring Brook Trail provides an important non-motorized route to many of the city's popular recreational amenities. The pathway begins just off the eastern terminus of the Rock River...
WI 5.1 mi Asphalt
In south-central Wisconsin, the Upper Yahara River Trail connects the communities of DeForest and Windsor along a beautiful wooded waterway. Buffered by neighborhoods, the trail offers residents an...
WI 2.9 mi Asphalt, Boardwalk
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 Badger State Trail, which heads south from Madison to the Illinois state line, is perhaps most famous for the 1,200-foot Stewart Tunnel—with a twist: the Stewart Tunnel is built on a...
WI 39.8 mi Asphalt, Crushed Stone
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
Overview The Capital City State Trail contributes to the impression that you’re never far from a bike path in the Madison area. The paved trail meanders for 17 miles from the suburb of Fitchburg in...
WI 17.2 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
The 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 Interurban Railway...
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
The Long Prairie Trail journeys across the width of agricultural Boone County for nearly 14 miles on the railroad corridor previously used by the Kenosha and Rockford Railroad, later known as the...
IL 13.9 mi Asphalt, 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
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
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
The North Mendota trail is a 12-ft wide asphalt trail that connects Waunakee and Governor Nelson State Park, on the shores of Lake Mendota. Starting at the northern trailhead in the village of...
WI 4.14 mi Asphalt, Boardwalk
The Old Plank Road Trail parallels State Route 23—a road originally built out of wooden planks in the 1800s—from the western edge of Sheboygan to the Village of Greenbush. The trail was one of the...
WI 37.6 mi Asphalt
The Peebles Trail is a nearly 6-mile pathway, linking Fond du Lac at the southern edge of Lake Winnebago with St. Peter (Taycheedah) to its east. The trail also passes through the unincorporated...
WI 5.6 mi Asphalt
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
The Prairie Trail offers a paved route of nearly 7 miles along the eastern boundary of Fond du Lac, a mid-sized city befitting its French name which means “foot of the lake” as it hugs the southern...
WI 6.7 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 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
Overview The Wild Goose State Trail is a premier rail trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. For trail users looking for a peaceful and beautiful place to visit,...
WI 34.5 mi Asphalt, Crushed Stone, Dirt, Grass
Madison’s Campus Drive Pedestrian and Bicycle Path is a short trail linking the city’s west side with the University of Wisconsin’s agricultural facilities. Both the heart of the university and the...
WI 0.8 mi Asphalt
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 Starkweather Creek Path traces the waterway north from the Capital City State Trail through Madison’s eastern neighborhoods of Starkweather, Worthington Park, Eken Park and Carpenter-Ridgeway. The...
WI 3.1 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
The 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. The Blue Route is the...
WI 8.9 mi Asphalt
Blackhawk Path offers a convenient way to traverse Shorewood Hills, a western suburb of Madison nestled along Lake Mendota. Increasing its value as a commuting corridor are plans to extend the trail...
WI 2.3 mi Asphalt
Fond du Lac's Brooke Street Trail follows a former rail corridor from the community's southern reaches to an endpoint not far from scenic Lake Winnebago. The city's location relative to the lake,...
WI 2 mi Asphalt
The CamRock Trail travels 2.4 miles through its namesake CamRock Park in Cambridge, Wisconsin. CamRock Park, managed by Dane County Parks, offers a number of ammenities to trail users including...
WI 2.4 mi Crushed Stone
The Downtown Trail—also known as the River Trail and Riverwalk Trail—runs alongside the Fond du Lac River for nearly 2 miles in the heart of Fond du Lac. The vast majority of the trail is smooth...
WI 1 mi Asphalt, Crushed Stone
The Harbor View Trail occupies a former rail bed—now shared with overhead electric transmission wires—on the southern edge of Lakeside Park in Fond du Lac. The trail parallels Harbor View Drive for...
WI 1.1 mi Asphalt
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
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
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
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
The southern Wisconsin City of Beloit, located near the Illinois border, boasts over 9 miles of multiuse trail along the Rock River. The river is the centerpiece of downtown, and a system of...
WI 9.2 mi Asphalt, Concrete
This path runs along the north side of Highway 11 and south of the city of Janesville. The eastern end starts about 3/4 of a mile west of I-39 and runs all the way to S County Road D, crossing over...
WI 3.8 mi Asphalt
The Wingra Creek Path—also known as the Wingra Bike Path—runs along the winding waterway in Madison. The trail provides a critical link from the neighborhoods south of downtown Madison to the Capital...
WI 1.9 mi Asphalt
The Yahara River Bike Path, on the northeastern side of Madison, is anchored by Tenney Park on one end and the 17-mile Capital City Trail on the other. From one recreational amenity to the other, the...
WI 0.9 mi Asphalt

Recent Trail Reviews

Jefferson County Interurban Trail

Map incomplete

June, 2024 by j.michael.klaus

As noted by the previous reviewer in June, 2023, this trail is now complete from its trailhead in Watertown to its junction with County Road F, south of Ixonia. It has been paved and open since October, 2022. Please update map. The map's satellite view actually shows the asphalt surface.

Ozaukee Interurban Trail (Route of the Badger)

Port Washington

June, 2024 by patrick.smith47203

Picked up the trail by Holiday Inn and went North. Nice run with limited traffic… good paved path to put in a few miles

White River State Trail (Route of the Badger)

Did the trail yesterday with my wife. Nice traffic bond trail with lots of shade and lots of dog poo left by unscrupulous pet owners . Why wreck this trail because you're too lazy to pick up after yourself . The world is not your toilet.

May, 2024 by johnschloegl

Did the trail yesterday with my wife. Nice traffic bond trail with lots of shade and lots of dog poo left by unscrupulous pet owners . Why wreck this trail because you're too lazy to pick up after yourself . The world is not your toilet.

Accordion

Pike River Pathway

goes a lot further south

April, 2024 by lpstaszewski

Nice trail crossing Hwy 20 is kind of a pain but south of that it is nice. It goes to Hwy KR which is a lot further than the map shows. You can even go to Petrified Springs by taking the pathway that runs parallel to Hwy 31.

Root River Pathway (Route of the Badger)

Charming, Tricky, Gritty

April, 2024 by deetiffanylb

Be aware. Signage not good 1st part of south end (where we began).
Trail Link map + GPS very helpful. Since signs are more in keeping w/ biking, than nose on phone, a suggestion: At decision points pls post signs, rather than down the road when you’ve luckily made a correct turn. Once through that the South end chains thru parks, many charming bridges over The Root River. North end signage was elusive too. We park near Zoo, biked along shore line, cut West to pick up trail just west of Main Street bridge and enjoyed 90% of the ride back toward North/car. A leisurely and scenic ride except for the navigation guessing game at beginning and end.

Long Prairie Trail

Nice trail

April, 2024 by christyfry14

We rode this trail along with the Stone Bridge Trail. The asphalt needs some repair but still a nice trail.

Brown Deer Recreational Trail

Oak Leaf > Ozaukee Interurban Connector

February, 2024 by davesnyder1622

Officially part of the Milwaukee County Oak Leaf Trail system, this connector joins the Oak Leaf loop at Brown Deer Park and meets the Ozaukee Interurban Trail seamlessly at County Line Road. Combined with the Oak Leaf’s Lakefront, River Line and Zip Line segments, they provide straight, smooth pavement on railbed between downtown Milwaukee and Cedarburg, and beyond.

Peebles Trail

Crushed stone was upgraded to asphalt by the end of 2022. Much smoother ride from end to end. Still absent a direct link into Lakeside Park.

November, 2023 by jmreese1

Crushed stone was upgraded to asphalt by the end of 2022. Much smoother ride from end to end. Still absent a direct link into Lakeside Park.

Military Ridge State Trail

Beautiful ride

November, 2023 by christyfry14

Rode from Mt. Horeb to Ridgeway and back. Beautiful countryside and the trail is great. All well kept. Can’t wait to go back!

Badger State Trail

Beautiful trail

November, 2023 by christyfry14

I’ve ridden this trail several times. It’s well kept. Most of it is shady and fairly flat.

Oak Leaf Trail (Route of the Badger)

South Shore Line

November, 2023 by thejake91739

On a perfect weekday morning in early October I experienced by bicycle the South Shore portion of the Oak Leaf Trail.
I parked in the Grant Park Beach parking lot in South Milwaukee and headed north to Cupertino Park and then back, a distance of about twelve miles. Even though it was such a short ride it took me over two hours since I had to frequently stop for the awesome photo ops. The views of the lake and the Milwaukee skyline are sensational!
The trail is obviously beloved by the community. Not only were there plenty of other bicyclists, but there were a tremendous amount of friendly pedestrians walking their dogs or getting their steps in, especially in Bay View Park.
The South Shore portion of the trail has so much to offer: woods, tree lined streets with charming homes, wildflowers, squirrels, geese, shoreline, lots of curves, five parks, yachts, and plenty of benches to take in the marvelous views of Lake Michigan and the downtown skyline. Besides the lake views, I especially enjoyed the curvy trail covered in golden leaves through the woods of Grant Park.

TWO WORDS OF WARNING:
1) There are hills.
2) There are cracked and uplifted portions of trail through the woods of Grant Park due to tree roots. They will effectively work like speed bumps and slow you down a bit.

However, all in all, this is an enjoyable ride and certainly worthy of your time and five stars!

Duck Lake Nature Area Trail

Easy walk on a grassy former railroad bed

October, 2023 by markwboettcher

This trail was actually a former C&NW railway that served Lake Geneva and terminated in Williams Bay. Service to Williams Bay started in 1888 and ended in 1965. Service to Lake Geneva ended in 1975. Thanks to Maxine Thoorsell for starting the conversion of turning this former railway into a nature trail. It is an easy grass covered walk and the trail is 1.7 miles in length. You can also access the trail at the boat launch to the west...behind the barn. A separate trail that is part of this former railway extends from Williams Bay Northeast up to Hwy 50 in the Kishwaukeetoe Conservancy

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