Find the top rated walking trails in Middleton, 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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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...
The Rockton Main Street Path is situated off the Rock River on the southern end of downtown Rockton, a charming Midwestern village near the Illinois–Wisconsin border. It begins at Settler's Park,...
The 52-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...
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....
The Dorr Road Bike Path begins at South Beloit Municipal Park and parallels the roadway for its entire length. The views are primarily residential. After about three-quarters of a mile (from the...
The US Highway 12 Path offers a convenient, non-motorized alternative to traveling on the highway. The paved pathway begins in Middleton and heads northwest paralleling the roadway, separated from...
The Great Sauk State Trail spans nearly a dozen miles connecting the communities of Sauk City, Prairie du Sac, and Merrimac. Built along the former Union Pacific Railroad, the smoothly paved...
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...
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...
Rail-trail fans know that Wisconsin’s Elroy-Sparta State Trail is famous for its three tunnels. The Badger State Trail, which heads south from Madison to the Illinois state line (where it connects...
The Military Ridge State Trail finds the high ground as it rolls across 40 miles of idyllic farmland from the outskirts of Madison to the historic mining town of Dodgeville. It follows an American...
The Williamson Parkway Bike Path offers a pleasant, paved route through a residential area in southern Rockton. The mile-long trail follows its namesake roadway from Freeport Road (also known as S....
There’s no debating the historical significance of the Jane Addams Trail. Not only is it named for a Nobel Peace Prize-winning social activist who grew up nearby, but the trail also passes the site of...
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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...
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...
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...
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...
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...
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As is apparent from the name, the trail sits atop a beside along the Wisconsin River. The trail is asphalt and easy to use for people of all ages and abilities. The trail begins in Edgewater Street in...
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...
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...
The Dorr Road Bike Path begins at South Beloit Municipal Park and parallels the roadway for its entire length. The views are primarily residential. After about three-quarters of a mile (from the...
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...
The Great Sauk State Trail spans nearly a dozen miles connecting the communities of Sauk City, Prairie du Sac, and Merrimac. Built along the former Union Pacific Railroad, the smoothly paved...
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...
Stretching from Afton to Janesville, the northern section of the Peace Trail offers a paved, tree-shaded route paralleling the Rock River and an active rail line. At its northern end, the trail merges...
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....
The paved trail running through Nick Saelens Memorial Park is a pretty one, with a loop around a small pond and much of it following a tree-lined creek. The park is nestled in the Village of Durand in...
The US Highway 12 Path offers a convenient, non-motorized alternative to traveling on the highway. The paved pathway begins in Middleton and heads northwest paralleling the roadway, separated from...
Rail-trail fans know that Wisconsin’s Elroy-Sparta State Trail is famous for its three tunnels. The Badger State Trail, which heads south from Madison to the Illinois state line (where it connects...
As is apparent from the name, the trail sits atop a beside along the Wisconsin River. The trail is asphalt and easy to use for people of all ages and abilities. The trail begins in Edgewater Street in...
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...
The Hidden Oaks Trail is a piece of Middleton's expanding shared use path system. It peels off from the North Fork Trail and heads east, passing the Capitol Ice Arena, into the Hinrich's Family Farm...
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...
If you’re looking for an invigorating motorized-trail experience, the Cheese Country Recreation Trail (aka the Tri-County Trail) won’t disappoint. If you’re on foot, hoof, or self-propelled two...
The 52-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...
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...
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...
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...
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...
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...
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...
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....
The 52-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...
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...
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The South Fork Trail is a multipurpose recreation path in the City of Middleton, a suburb of Madison, Wisconsin. It winds east to west, from beneath US-12/14 to the Pleasant View Golf Course. The...
The US Highway 12 Path offers a convenient, non-motorized alternative to traveling on the highway. The paved pathway begins in Middleton and heads northwest paralleling the roadway, separated from...
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...
The Wild Goose State Trail is a premier rail-trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. If you are looking for a peaceful and beautiful place to visit, this trail has it...
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...
Stretching from Afton to Janesville, the northern section of the Peace Trail offers a paved, tree-shaded route paralleling the Rock River and an active rail line. At its northern end, the trail merges...
The Deming Way Trail is a recreational path along Pheasant Branch in Middleton, Wisconsin. The two-lane trail accommodates walkers, joggers, dog-walkers and cyclists. Though short, the trail connects...
The Military Ridge State Trail finds the high ground as it rolls across 40 miles of idyllic farmland from the outskirts of Madison to the historic mining town of Dodgeville. It follows an American...
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...
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The North Fork Trail begins beside US-12, intersecting with Middleton's other multiuse trails: specifically the US Highway 12 Path; Pheasant Branch Creek Corridor Trail; and the Deming Way Trail. The...
The Hidden Oaks Trail is a piece of Middleton's expanding shared use path system. It peels off from the North Fork Trail and heads east, passing the Capitol Ice Arena, into the Hinrich's Family Farm...
The Rockton Main Street Path is situated off the Rock River on the southern end of downtown Rockton, a charming Midwestern village near the Illinois–Wisconsin border. It begins at Settler's Park,...
The Williamson Parkway Bike Path offers a pleasant, paved route through a residential area in southern Rockton. The mile-long trail follows its namesake roadway from Freeport Road (also known as S....
If you’re looking for an invigorating motorized-trail experience, the Cheese Country Recreation Trail (aka the Tri-County Trail) won’t disappoint. If you’re on foot, hoof, or self-propelled two...
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...
Beautiful trail between Lake Mills and Deerfield. Ice cream in Deerfield! No ruts - hard packed crushed limestone. I rode my road bike with out problem. Just wish they had ice
This trail is short but riding from Middleton to Pleasant View is mostly uphill! Tough for recreational bikers. But pretty ride.
Went 20+ miles without seeing a sole, great trails, little rough in spots. One washout we barely missed that would have put you deep into your seatbelts
Such a terrible disappointment! Shame on the Wisconsin Department of resources for not maintaining this trail! We biked this trail about 20+ years ago with our children and it was wonderful. We started in Brodhead and we biked to Monticello and back to Brodhead. Yesterday my husband and I started in New Glarus and we biked to Albany and back to New Glarus. The only highlight was breakfast at the M&M Café in Monticello. This cafe has not changed in 20 some years💕.
I honestly don’t think there has been any crushed lime stone put down in that trail since we biked it last. Why is the department of natural resources not maintaining this trail? You have an absolute gold mind here, please realize it’s a value and put some time into it. Cut the grass on both sides of the trail, put down new lime stone!
The Chalet Landhaus is a wonderful place to stay a New Glarus, it is right on the trail.
We absolutely loved this trail. We started near the airport in Watertown Wisconsin and took the back roads all the way to the end of the marked trail. There’s a small 2 mile segment that’s a long state route 16 but it’s a dedicated trail on the side of that road. Loud traffic but just a small section so not that bad of a deal. Everything else is beautiful country roads very little traffic absolutely wonderful rolling Hhills and farmland. It took us three hours round-trip very leisurely pace of 9 mph Be sure to eat at the Main Street diner in Watertown
Just hit the trail today from Tutty's Crossing in Freeport all the way to Wisconsin state line (35 miles round trip). It's been 3 years this month since my last ride there. It's in great shape and the weather was perfect. Great scenery for small towns and farmland. Plenty of food, drink and shopping in Freeport. (Definitely check out Union Dairy at Douglas and Adams!)
5 star trail for any serious biker.
We did an 10.5 mile stretch from Elroy, WI to about 3 miles south of Wonewoc. Round trip 21 miles. We intended to do 30 miles but we're getting older and the air quality was terrible due to fires in Canada. That said this is a beautiful trail, very scenic, smooth, and a pretty flat easy ride. At a few of the road crossings the ends of the trail were filled in with sand instead of gravel, so watch out so you don't lose control. We chose the 400 due to having lots of stops with bathrooms. We were not disappointed. All of the facilities are clean and well maintained. Most of the small towns along the way have food and beer available, and the local folks are very welcoming and proud of their association with the trail. This has become our favorite WI trail. We hope to get back out there next year and finish the trail.
We camped at Blue Mound State Park and biked the first day to Dodgeville. The camp is at mile marker 22, so 36 miles round trip. Great scenery as the elevation is high: distant farmlands, golf courses, forest,…. The trail is in great condition, winding and rolling throughout farmlands, wooded area, prairies, and small rural communities. Our return trip was in misting rain and the forecast for storms later that week canceled our plans for the eastern leg until another time.
First time on the trail. I had a mountain bike, which was appropriate. Trail was mostly two 8-10 inch bare patches with grasses/weeds between. Otherwise, it was fine. Covered bridge was a surprise.
The prairie restoration is simply beautiful!! Many wildflowers were in bloom. This is a wonderful ride and highly recommend.
I rode the 400 trail from Reedsburg to Elroy as the last 20 miles of my ride from Madison this morning. I am midway through a cross country ride from Maine to Washington. Very grateful for rail trails like this one! Nice to have frequent public bathrooms, hard packed gravel, and shade. Some of the bridges are quite bumpy. Beautifully maintained town campsite in Elroy!
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