4.8
(58)
2,188
riders
114
rides
Road cycling routes around Middleton feature a diverse network of trails, from well-paved paths to routes with significant elevation gains. The region is characterized by rolling hills of Wisconsin farmland, scenic views of prairies, and natural areas like Pheasant Branch Conservancy and Lake Mendota. These routes connect to various parks and natural features, offering varied terrain for different cycling preferences.
Last updated: May 8, 2026
5.0
(2)
105
riders
71.9km
03:22
730m
740m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
88
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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58
riders
67.8km
03:34
990m
990m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(2)
29
riders
63.7km
02:54
640m
640m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.0
(1)
16
riders
18.0km
00:46
140m
140m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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A super nice spot to stop with great views out over the river.
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Dent a lovely village with shops / cafes / pubs perfect for a stop on The Dales Way.
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Very busy at weekend/ bank hols with. Motor bikes parking up for a natter
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Fleet Moss from Hawes is a remote and challenging Dales climb, averaging 8% with punishing ramps up to 20%. The narrow, weather-beaten road rises sharply through open moorland, with rough tarmac and exposed sections that make wind a serious factor. The steepest gradients hit early, so shift into your lowest gear and settle into a controlled, steady rhythm. Reaching the summit feels wild and raw—true Yorkshire climbing at its toughest.
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Tough climb with some 20% sections. Good surface and great views on a clear day.
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Dent Town in the heart of Dentdale is a real chocolate box village. With its beautiful cobbled streets, historical architecture, accommodation offerings, two pubs, shops and cafes, it offers a great day out or place to stay when adventuring in the area.
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Middleton offers a wide selection of road cycling routes, with over 110 routes available on komoot. These routes cater to various skill levels, including easy, moderate, and difficult options.
Road cycling in Middleton is characterized by a diverse network of trails, ranging from well-paved paths to routes with significant elevation gains. You'll encounter rolling hills of Wisconsin farmland, scenic prairies, and natural areas like Pheasant Branch Conservancy and Lake Mendota. The routes connect to various parks and natural features, offering varied terrain for different cycling preferences.
Yes, Middleton offers several easy, well-paved routes suitable for families. The Millthrop Bridge – Lanes Into Dentdale loop from Sedbergh School is an easy option, covering about 11 miles with minimal elevation gain. Additionally, the Pheasant Branch Creek Corridor Trail is a 1.4-mile paved, shaded path that is great for a relaxed ride.
Middleton's road cycling routes offer picturesque views of rolling Wisconsin farmland, expansive prairies, and serene water features. Routes like the Ribblehead Viaduct – Devil's Bridge loop from Lune Access - Killington Newbridge provide scenic vistas around Lake Mendota. You can also enjoy views of red barns and wind turbines along paths like the Middleton to Sauk City path.
Absolutely. For experienced cyclists seeking a challenge, Middleton offers routes with notable elevation gains. The Dent Village – View of Dent Head Viaduct loop from Sedbergh School is a difficult route covering over 42 miles with significant climbing. The Middleton to Sauk City path also includes a mile-long gradual hill climb for those looking to test their endurance.
Many routes pass by or near significant natural attractions. The Pheasant Branch Conservancy, Middleton's 'scenic jewel,' features protected prairie, woods, and waterways, with Fredrick's Hill offering spectacular 360-degree views including an effigy mound and the Wisconsin State Capitol. Lake Mendota, the largest glacial lake in the area, is also a prominent feature. For specific natural monuments, you might encounter highlights like Thornton Force waterfall or Low Force Waterfall (Force Gill).
The road cycling routes in Middleton are highly rated by the komoot community, with an average score of 4.77 stars from over 59 reviews. More than 2,000 road cyclists have used komoot to explore Middleton's varied terrain, often praising the diverse landscapes and well-maintained paths.
Yes, Middleton features several circular road cycling routes. Examples include the Lanes Into Dentdale – Dent Village loop from Sedbergh School, which offers a moderate ride through farmland, and the View of Sunbiggin Tarn – Orton Scar Café loop from Sedbergh School, another moderate loop option.
Middleton is home to over 36 parks and natural areas, and more than 30 miles of multi-use trails. For more detailed information on trails and parks, you can visit the official Middleton tourism website: visitmiddleton.com/recreation/trails-and-parks/.
Middleton offers pleasant road cycling conditions through much of the year. Spring and fall provide comfortable temperatures and beautiful scenery, especially with the changing foliage. Summer is also popular, though it can be warmer. Winter cycling is possible, but conditions may vary with snow and ice.
Yes, Middleton's trail system is well-connected. The Blackhawk Path, for instance, travels along University Avenue and links to other trails in Madison, offering a convenient route into the state's capital. The Middleton Bike Trail System also connects to many nearby parks and natural areas.
While specific cafes on every route are not listed, many routes, especially those connecting to downtown Middleton via the Loop Trail, will bring you close to amenities. For general information on local attractions and services, you might find useful resources on the Middleton tourism website: visitmiddleton.com/urban-outdoors/.


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