5.0
(3)
171
riders
2
rides
Road cycling around Diamond Bluff, Wisconsin, is characterized by its prominent limestone bluffs and proximity to the Mississippi River. The region features unglaciated bedrock layers and offers scenic vistas from elevated positions. Road cyclists can expect varying elevations, with routes often following the Wisconsin Great River Road. This area provides a blend of riverfront cycling and climbs along the bluffs.
Last updated: May 28, 2026
5.0
(2)
22
riders
26.3km
01:25
160m
160m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(1)
143
riders
78.4km
03:52
460m
460m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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5.0
(1)
18
riders
50.3km
02:22
280m
280m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5
riders
71.4km
03:12
530m
530m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
1
riders
57.3km
02:30
340m
340m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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This off-road, paved trail runs for 10 miles along County Road 21 from the bottom of Flower Valley near Wacouta on Highway 61 up to the top of the valley at State Highway 58 near Minnesota State College Southeast–Red Wing Campus. Bullard Creek flows through this valley before emptying into the Mississippi River. OpenStreetMap-based apps show the trail extending nearly to Highway 61, but in reality, it begins at Circle South Road. Trail users must park on Circle South Road; there is no parking lot and no restrooms. The views of Flower Valley, the Mississippi Valley, and the towering bluffs on the opposite side of the Mississippi make this trail well worth a visit.
4
0
fund to look up at the ski resort when skiing passed on your skate skis
3
0
Parking lot and access to both the DNR nature loop and the Cannon Valley Trail.
1
0
A rest area with a nice roof on it I have used several times to skip out of rain during biking season.
1
0
Nice shelter, I have had to use this before in a rainstorm.
1
0
It's always hard to tell if this parking lot is allowed to be driven in to, because they have all kinds of signs saying "Don't Drive In Here" since it's also an access point of the fairground. But still there is a nice picnic table and it's quiet.
0
0
A big lake, gets pretty green and dirty depending on the time of year, but a nice landmark all the same.
1
0
There are {{total_tours}} road cycling routes around Diamond Bluff listed on komoot. These routes offer a variety of distances and elevations, catering to different skill levels.
Yes, Diamond Bluff offers easy road cycling options perfect for families or those new to the sport. One excellent choice is the Welch Village – Belle Creek Rest Area loop from A. P. Anderson Park, which is rated as easy and covers a distance of approximately 26 km.
Road cycling around Diamond Bluff offers stunning natural landscapes, primarily featuring the majestic Mississippi River and dramatic limestone bluffs. You'll experience panoramic river vistas, especially from elevated points like the Overlook. The area is also part of the scenic Wisconsin Great River Road, providing a blend of riverfront views and rural charm.
While cycling, you can enjoy views of the prominent limestone bluffs that define the region. Nearby attractions include the Trenton Bluff Prairie State Natural Area, known for its rare dry prairie ecosystem and sweeping river views. You might also pass by riverfront parks like Levee Park on the Red Wing (Minnesota Riverfront) or Bay Point Park, which offer great spots to observe the Mississippi River.
The best time for road cycling in Diamond Bluff is generally during the spring, summer, and fall months. These seasons offer pleasant temperatures and vibrant scenery. Fall, in particular, can be spectacular with changing foliage along the bluffs and river. Always check local weather conditions before heading out.
Yes, for more experienced riders seeking a challenge, routes with greater elevation gain are available. The Lone Mound loop from River Falls, for example, is rated moderate and features over 500 meters of elevation gain over its 71 km distance, offering a good workout with rewarding views.
While specific dedicated cycling parking isn't extensively detailed, general parking is available at various public access points. Parks like Sea Wing Memorial Park or Diamond Bluff Landing offer public access and likely parking. For routes starting from nearby towns, check local park facilities such as A. P. Anderson Park or those in Red Wing.
The komoot community rates road cycling in Diamond Bluff highly, with an average score of {{rating_score}} out of 5 stars. Cyclists often praise the scenic beauty of the Mississippi River and the challenging yet rewarding climbs of the bluffs, especially along the Wisconsin Great River Road.
Yes, many of the road cycling routes around Diamond Bluff are designed as loops, allowing you to start and end at the same point. Examples include the Cannon Valley Trail – Belle Creek Rest Area loop from Red Wing and the Welch Village – Belle Creek Rest Area loop from Red Wing, offering convenient circular journeys.
While Diamond Bluff itself is a smaller community, nearby towns along the Wisconsin Great River Road, such as Red Wing (Minnesota) or Hager City (Wisconsin), offer a selection of cafes, pubs, and restaurants where cyclists can refuel and relax. It's advisable to plan your route to pass through these towns if you're looking for specific amenities.
The road cycling routes around Diamond Bluff vary significantly. You can find shorter, easier routes around 26 km with about 160 meters of elevation gain, like the Welch Village – Belle Creek Rest Area loop from A. P. Anderson Park. For longer rides, options extend up to 71 km with over 500 meters of climbing, such as the Cannon Valley Trail – Belle Creek Rest Area loop from Red Wing, offering diverse challenges for all levels.


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