27
riders
1
ride
Touring cycling around Crestwood is characterized by its riverine settings and extensive greenway trails. The area features paths along the Meramec River, offering views of limestone bluffs and woodlands. These greenway trails provide a mix of paved and natural surfaces, often with gradual elevation changes. The landscape combines urban and natural environments, making it suitable for various cycling preferences.
Last updated: July 8, 2026
14
riders
50.8km
02:58
220m
220m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
7
riders
39.1km
02:19
200m
200m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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1
riders
47.6km
02:53
360m
360m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
riders
52.4km
03:03
230m
230m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Crestwood
The Lewis and Clark Bridge was built to connect two disjointed stretches of Interstate 265, to form part of the Louisville ring road. Ample space was built in for pedestrian and bicycle access.
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Big Four Station Park covers ten acres at the base of the Big 4 Bridge. It is a picturesque spot with plenty of green space, restrooms, picnic tables, paved pathways, and a bike-sharing station. It is a hub for walkers and cyclists traveling between Louisville and Indiana. There are stunning views of the Ohio River and the Louisville skyline, and the bridge is filled with lights at night, making it a popular destination in the evening. There is also a great local farmers market here on Saturdays.
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boat landing with some tables and a shelter. easy spot to pull off and watch the river
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The Big Four Bridge, originally completed in 1895 as a railroad bridge, now connects Louisville, Kentucky, and Jeffersonville, Indiana, for pedestrians and cyclists. After closing for rail use in the sixties, the bridge reopened in 2013 with ramps for walkers and bikers. Spanning 2,525 feet, the bridge offers a two-mile roundtrip, including the ramps. It attracts an average of 1.5 million visitors annually, making it a key recreational link between the two cities. There are bike rental places close by to the bridge too.
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Sleepy Hollow Lake is a long narrow lake by the South Fork of Harrods Creek. This is a good place to slow down and look for animals as you ride around the area.
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There are several touring cycling routes around Crestwood. Our guide features 5 distinct routes, all rated as moderate difficulty, offering a good range of options for cyclists.
The touring cycling routes featured in our guide for Crestwood are all rated as moderate. This means they offer a good balance of challenge and accessibility, suitable for most touring cyclists. The region's greenway trails often feature gradual elevation changes, making them enjoyable for various fitness levels.
Yes, Crestwood offers routes that provide longer touring experiences. For example, the Big Four Bridge – Big Four Station Park loop from Green Spring covers over 51 kilometers, while the Sleepy Hollow Lake – Meeting Street Stone Pillars loop from Worthington is nearly 48 kilometers long. These routes allow for extended rides through varied landscapes.
Crestwood's touring cycling routes often feature a mix of paved surfaces, especially along the extensive greenway trails. You can expect to encounter riverfront paths and wooded areas, particularly along the Meramec River, offering picturesque views of limestone bluffs and lush woodlands. Routes like the Bridge Over Floyds Fork – Louisville Loop Trail loop from Eastwood provide a diverse experience.
The area is highly rated by the komoot community, with an average score of 4.75 stars. Reviewers often praise the diverse scenery and the array of options available to suit different skill levels, from urban landscapes to natural riverine settings.
Yes, many of the touring cycling routes in Crestwood are designed as loops, providing a convenient way to start and end your ride at the same point. Examples include the Bridge Over Floyds Fork – Pope Lick Trestle Memorial loop from Eastwood and the Big Four Station Park – Lewis and Clark Bridge loop from Lewis and Clark Bridge.
Crestwood's routes are characterized by riverine landscapes and woodlands. Cyclists frequently encounter riverfront paths and wooded areas, especially along the Meramec River, offering views of limestone bluffs and lush forests. The greenway trails provide scenic passages through these natural environments.
While all routes in our guide are moderate, the extensive greenway trails in Crestwood, such as the Meramec Greenway Trail and Grant's Trail, are generally accessible and well-suited for families. Their gradual elevation changes and paved surfaces make for a comfortable ride for various ages and skill levels.
The spring and fall seasons generally offer the most pleasant conditions for touring cycling in Crestwood, with milder temperatures and beautiful foliage. Summer can be enjoyable, but it's advisable to start earlier in the day to avoid the peak heat. Winter cycling is possible, but be mindful of colder temperatures and potential icy patches.
While our guide doesn't list specific highlights for these routes, the region itself is rich in attractions. The Meramec Greenway Trail connects to numerous regional parks, and areas like Whitecliff Park offer additional recreational opportunities. The routes often weave through both urban and natural landscapes, providing varied points of interest.
For those looking for a longer ride, the Big Four Bridge – Big Four Station Park loop from Green Spring spans over 51 kilometers. Another excellent option is the Sleepy Hollow Lake – Meeting Street Stone Pillars loop from Worthington, which is nearly 48 kilometers long, offering a substantial touring experience.


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