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Routes
Road cycling routes
United States
Kentucky
Oldham County

Crestwood

The best road cycling routes around Crestwood

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.

Best road cycling routes around Crestwood

  • The most popular road cycling route is Crestwood Gardens – Maples Park loop from Crestwood, a 32.2 miles (51.8…

Last updated: May 28, 2026

16

riders

#1.

Crestwood Gardens – Maples Park loop from Crestwood

51.8km

02:19

220m

220m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Popular around Crestwood

Hiking around Crestwood

Cycling around Crestwood

Tips from the Community

AaronLavanchy
August 11, 2023, Maples Park

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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Top of the climb called the Prison Stomp

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One of the largest Giant dealers in the USA. Ross Horsley is the man to see!

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Frequently Asked Questions

How many road cycling routes are available in Crestwood?

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.

What is the general difficulty level of road cycling routes in Crestwood?

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.

Are there easy road cycling routes for beginners in Crestwood?

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.

What kind of terrain can I expect on road cycling routes around Crestwood?

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.

Are there scenic viewpoints or landmarks along the road cycling routes in Crestwood?

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'.

What is the typical length of road cycling routes in Crestwood?

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).

Are there loop trails for road cycling in Crestwood?

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.

What do other road cyclists enjoy most about road cycling in Crestwood?

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.

Are there family-friendly road cycling options in Crestwood?

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.

Is parking available near road cycling routes in Crestwood?

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.

What is the best time of year for road biking in Crestwood?

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.

Most popular routes around Crestwood

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