4.5
(2)
270
riders
37
rides
Road cycling around Crestwood, Missouri, offers a variety of routes that traverse diverse scenery. The region features greenways and wooded areas, providing accessible paths for cyclists. Routes often include moderate elevation changes, with some paths designed for higher fitness levels. This landscape provides a range of experiences, from easier rides to more challenging excursions.
Last updated: May 28, 2026
16
riders
51.8km
02:19
220m
220m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
51.6km
02:25
320m
320m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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5.0
(1)
8
riders
41.1km
02:46
330m
330m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
6
riders
58.4km
02:58
510m
510m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5
riders
42.3km
01:59
310m
310m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Crestwood
Maples Park sits on 22 acres and gets its name from the abundant maple trees on-site. It offers something for everyone, including: old restored barn structures, picnic tables, tree swings, and large open fields.
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One of the largest Giant dealers in the USA. Ross Horsley is the man to see!
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Crestwood offers a diverse selection of over 30 road cycling routes. These routes cater to various preferences, with 5 easy options and 30 moderate routes, ensuring there's something for every cyclist.
The majority of road cycling routes in Crestwood are classified as moderate, making them suitable for cyclists with a good fitness level. There are also several easy routes available for those seeking a more relaxed ride. Routes often feature moderate elevation changes, with some paths designed for higher fitness levels.
Yes, Crestwood offers 5 easy road cycling routes, perfect for beginners or those looking for a more leisurely ride. These routes typically feature well-paved surfaces and gentler terrain, such as the Crestwood Gardens – Maples Park loop from Crestwood, which is a moderate route but offers varied landscapes.
Road cycling routes in Crestwood traverse diverse scenery, including greenways and wooded areas. You can expect mostly well-paved surfaces, with some routes featuring moderate climbs and varied landscapes. For example, the Prison Stomp - Top of the climb loop from O'Bannon offers a consistent ride through natural corridors.
While specific landmarks are not detailed for every route, the region's routes are known for their scenic beauty, particularly through wooded areas and along greenways. The Railroad Viewpoint loop from Crestwood suggests opportunities for scenic vistas, and the region research mentions a 'scenic ride on Woods Avenue through the woods'.
The road cycling routes in Crestwood vary in length, generally ranging from approximately 25 miles (40 km) to over 37 miles (60 km). For instance, the Prison Stomp - Top of the climb loop from Orchard Grass Hills is about 25.5 miles (41.1 km), while the Railroad Viewpoint loop from Crestwood extends to nearly 36.3 miles (58.4 km).
Yes, many of the road cycling routes in Crestwood are designed as loops, offering convenient starting and ending points. Examples include the popular Crestwood Gardens – Maples Park loop from Crestwood and the Crestwood Gardens – Maples Park loop from O'Bannon.
The road cycling experience in Crestwood is highly rated by the komoot community, with an average score of 4.7 stars. Cyclists often praise the varied terrain, the presence of greenways, and the accessible paths that cater to different ability levels, from easy rides to more challenging excursions.
While specific 'family-friendly' designations are not always explicit for road cycling, the presence of 5 easy routes and greenways suggests options suitable for families. Routes with mostly well-paved surfaces and lower elevation gains would be ideal for a family outing.
While specific parking locations are not detailed for every route, the presence of numerous trails and greenways in and around Crestwood suggests that parking facilities are generally available at trailheads or nearby public access points. It's advisable to check local park information for specific parking details.
The region's diverse scenery and wooded areas suggest that spring and fall would offer pleasant temperatures and beautiful foliage, making them ideal seasons for road cycling. Summer can also be enjoyable, though it's wise to consider morning or late afternoon rides to avoid the midday heat.


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