Oconomowoc, WI Inline Skating Trails and Maps

809 Reviews

Looking for the best Inline Skating trails around Oconomowoc?

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

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Activities
Length
Surfaces
Type
51 Results
Activities
Length
Surfaces
Type

Cannonball Path

3.9 mi
State: WI
Asphalt

Capital City State Trail

17.2 mi
State: WI
Asphalt

Eisenbahn State Trail

24.3 mi
State: WI
Asphalt, Crushed Stone

Glacial Drumlin State Trail

53.2 mi
State: WI
Asphalt, Crushed Stone, Gravel

Hank Aaron State Trail

15.2 mi
State: WI
Asphalt, Crushed Stone

KR Trail

1.5 mi
State: WI
Asphalt, Boardwalk

Kenosha County Bike Trail

7.9 mi
State: WI
Asphalt

Kenosha Pike Bike Trail

6.95 mi
State: WI
Concrete

Kiwanis Bike Trail

4 mi
State: WI
Asphalt

Lake Andrea Multi-Use Path

2.3 mi
State: WI
Asphalt

Lower Yahara River Trail

4.1 mi
State: WI
Asphalt, Boardwalk

Meadowbrook Trail

2.4 mi
State: WI
Concrete

Milwaukee RiverWalk

3.1 mi
State: WI
Concrete

New Berlin Recreation Trail

7 mi
State: WI
Asphalt

Oak Leaf Trail

123.6 mi
State: WI
Asphalt

Ozaukee Interurban Trail

30.1 mi
State: WI
Asphalt

Peace Trail

12.3 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

Rock River Parkway Trail

2.4 mi
State: WI
Asphalt, Concrete
Accordion

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

Badger State Trail

39.8 mi
State: WI
Asphalt, Crushed Stone

Beerline Trail

3.7 mi
State: WI
Asphalt

Fox River Trail (WI)

6 mi
State: WI
Asphalt

Lake Country Trail

15.2 mi
State: WI
Asphalt

Military Ridge State Trail

40 mi
State: WI
Asphalt, Crushed Stone

Old Plank Road Trail (WI)

37.6 mi
State: WI
Asphalt

Prairie Trail (WI)

6.7 mi
State: WI
Asphalt

Root River Pathway

6.6 mi
State: WI
Asphalt

Seven Waters Bike Trail

18.6 mi
State: WI
Asphalt, Crushed Stone, Gravel

Sheboygan Interurban Trail

14 mi
State: WI
Asphalt

Starkweather Creek Path

3.1 mi
State: WI
Asphalt

Stone Mill Trail

1.5 mi
State: IL
Asphalt

West Allis Cross Town Connector

0.9 mi
State: WI
Asphalt

Kinnickinnic River Trail

2.3 mi
State: WI
Asphalt

Powerline Trail (WI)

4.4 mi
State: WI
Asphalt

Lake Geneva Bike Path

8.9 mi
State: WI
Asphalt

Blackhawk Path

2.3 mi
State: WI
Asphalt

Brooke Street Trail

2 mi
State: WI
Asphalt

Downtown Trail (WI)

1 mi
State: WI
Asphalt, Crushed Stone

Harbor View Trail

1.1 mi
State: WI
Asphalt

North Shore Trail (WI)

3 mi
State: WI
Asphalt

Racine County Bike Trail

1.4 mi
State: WI
Asphalt, Concrete

Racine-Sturtevant Trail

3.5 mi
State: WI
Asphalt

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 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 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 the...
WI 17.2 mi Asphalt
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 used as...
WI 24.3 mi Asphalt, Crushed Stone
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 gigantic sheets...
WI 53.2 mi Asphalt, Crushed Stone, Gravel
The Hank Aaron State Trail, which spans the breadth of Milwaukee County, begins at Lakeshore State Park in Milwaukee, where it overlooks Lake Michigan to the east and provides breathtaking views of...
WI 15.2 mi Asphalt, Crushed Stone
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
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
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
Dane County's Lower Yahara River Trail offers an incredibly scenic experience in the Madison area. On its western end, the 4.1-mile paved pathway connects to the Capital City State Trail near the...
WI 4.1 mi Asphalt, Boardwalk
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
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
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 trestles,...
WI 7 mi Asphalt
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 flat rural...
WI 123.6 mi Asphalt
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 stretches the...
WI 30.1 mi Asphalt
Stretching from Janesville to Beloit, 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 leaves off...
WI 12.3 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
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 farms and...
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
Accordion
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
Closure Notice: The Stewart Tunnel has been closed since 2019 and remains closed for the foreseeable future. A detour using Tunnel Road allows trail users to go around the tunnel. Visit the trail page...
WI 39.8 mi Asphalt, Crushed Stone
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 central...
WI 3.7 mi Asphalt
The Fox River Trail runs diagonally along its namesake waterway through Waukesha in southeastern Wisconsin (just outside of Milwaukee). The trail is part of the Route of the Badger, a Milwaukee-area...
WI 6 mi Asphalt
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 Interurban Railway...
WI 15.2 mi Asphalt
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 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 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
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 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, locally...
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
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 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. The trail leaves from a junction with the New Berlin...
WI 0.9 mi Asphalt
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
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 4.4 mi Asphalt
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. The Lake Geneva Bike...
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 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
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
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

Bugline Trail

Nice paved trail except for all the road crossings at the south end

July, 2026 by y1htak2

We started in downtown Menomonee Falls. We parked in Mill Pond Park on Roosevelt, then rode our bike over to Water Street where the trail begins. That probably wasn’t the best place to start because we had to cross the two scary intersections; Highway 175 with a crossing light and Main street on a long diagonal with no crossing light.

This is a very nice trail with wooded areas that pass through residential areas and some business areas. The northern end has some fields. On the southern end you have to stop to cross at a lot of roads all the way to and through Sussex. Luckily the car drivers are very courteous and stop to let you cross. It was nice to see kids of all ages on the trail. It’s pretty flat until you get past the Fireman’s Park soccer fields in Merton. Then you have some pretty steep hills.

Mascoutin Valley State Trail

A nice country trail in 2 segments but hard to find trailheads and parking

July, 2026 by y1htak2

Made up of 2 nice country trails with mostly decent crushed limestone surface separated into 2 parts by highway 23 which is an unsafe, busy, fast highway with a pretty wide gravel shoulder. There are no toilet facilities. Some biting flies if you stop but we didn’t get any ticks.

We first attempted to ride the Ripon to Berlin segment. In Ripon you can park slightly past the start of the trail off Locust where there is a nice parking area and pavilion. We only got about 6 miles or so before we had to stop for a very large downed tree. We could have stopped at Vines and Rushes Winery but it was a little early for us.

At the Berlin side of the trail there was a sign in a grassy area for parking across the street from where the grassy trail begins at Berlin Feed. Didn't look like that end of the trail got much use. It wasn’t worth getting tandem bike out of van to ride just a few miles so didn’t ride that part.

Then we rode our bike from Rosendale to Fond du Lac. We parked along the side of Zamzow (neighborhood) Park on Willow Creek Rd just off North St. We rode the short segment to Hwy 26 and then turned around and rode to Fond du Lac where trail ends on VVV with trail head parking.

Wild Goose State Trail

Beautiful shaded part of the trail in Fond du lac county. Four tree areas blocking path southwest of Oakfield.

July, 2026 by barb.frank0709

Beautiful shaded part of the trail in Fond du lac county. Four tree areas blocking path southwest of Oakfield.

Accordion

Lake Geneva Bike Path

Agree with other Reviews

July, 2026 by jboepple

Poorly marked. Several sections are in need of repair. Several unexpected "end of trail" dead ends. Very disappointed. Wish a safe route was created to hook up with the White River State Trail, which is only a few miles away, but to access it you need to traverse country roads posted at 55 MPH and with little to no shoulder.

Military Ridge State Trail

Rider Beware

June, 2026 by nhx9h7gjw7

Love this trail but rode today between Riley and Brigham County Park and found the trail to be in extremely rough shape on either side of Mt. Horeb. Lots of ruts, giant holes and loose sand. Slow your roll and pay attention to utility flags and sticks identifying some of the bigger holes. Stay safe!

Wild Goose State Trail

beautiful trail

June, 2026 by 47gkpg2wy5

Beautiful country trail. A lot of tree cover and not very many other people. Worth the ride.

Glacial River Trail

a lot of road riding

June, 2026 by 47gkpg2wy5

We took this trail from the Wild Goose trail but had no idea we would be on so many roads. As you got closer to Watertown, you are also on the road. We personally try to avoid roads as much as possible so we didn’t like this part. We only went to Watertown from the North so I am not sure what the rest of the trail is like. The actual bike paths are great.

Seven Waters Bike Trail

flat

June, 2026 by sterp8

I think it was a nice trail. We started out in Rochester and went north Very flat so there is constant pedaling. Good signage. No bathrooms until Meyer Park or Heg park and pray they are open.

White River State Trail

Update!

June, 2026 by b7ggzfh8h9

As of June 15th, the trail is now open between Burlington and Lyon.

White River State Trail

Between Spring Valley road trailhead and Lyon the trail was closed due to 2 bridges being washed out

May, 2026 by fredklausegger

Between Spring Valley road trailhead and Lyon the trail was closed due to 2 bridges being washed out

Muskego Recreation Trail

Beautiful trail with varying gravel conditions

May, 2026 by nkanute

great gravel cycling! Everyone complaining must be riding some skinny tires or should stick to the oak leaf- this was a very fun ride (I run 40mm semi slick tires and had no issues)

Kenosha County Bike Trail

Lots of shade and well maintained

April, 2026 by gypsycyn

A short but pleasant ride, with lots of shade, smaller wildlife, rest benches, even a couple pet stops with water dishes for the fur babies.

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