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Road cycling routes
United States
Kentucky
Jefferson County

Rolling Hills

The best road cycling routes around Rolling Hills

By Fede from komoot

·

Updated May 28, 2026

If you've ever tried to plan road cycling around Rolling Hills, you know how quickly the options can become overwhelming. With so many roads and loops, it's tough to tell which routes are genuinely worth your time and effort, and which are just filler. We get it — nobody wants to waste precious saddle time on a mediocre ride. That's why we've done the legwork for you. Our komoot community has mapped, ridden, and reviewed the best of the best, so this guide is your curated shortcut to the routes that truly deliver.

Road cycling around Rolling Hills is defined by its dynamic, undulating terrain. Expect a rewarding mix of rolling hills, steep canyons, and coastal bluffs that offer consistent elevation changes without extreme, punishing climbs. What truly sets it apart are the panoramic views of the Pacific Ocean, the rugged coastline, and even Catalina Island on clear days, all enjoyed from well-paved surfaces. The region offers everything from moderate loops to more challenging climbs, catering to a wide range of abilities.

If you only do one ride, make it the Prison Stomp - Top of the climb – Gathright Hill loop from Worthington. At 52.3 miles (84.2 km) with consistent rolling hills, it’s a fantastic endurance ride that showcases the region's character. For a slightly shorter, scenic journey with moderate elevation changes, we'd point you to the Maples Park – Crestwood Gardens loop from Moorland, a local favorite covering 33.8 miles (54.3 km). Ready to explore? Dive into these routes and discover why over 600 road cyclists have already used komoot to experience Rolling Hills.

If you only do 3 of these routes

  1. 1

    Prison Stomp - Top of the climb – Gathright Hill loop from Worthington
  2. 2

    Maples Park – Crestwood Gardens loop from Moorland
  3. 3

    Prison Stomp - Top of the climb – Middletown Cycling Shop loop from Hickory Hill

Compare these routes at a glance

Trail

Distance

Elevation

Difficulty

Prison Stomp - Top of the climb – Gathright Hill loop from Worthington

84.3 km

640 m

Moderate

Maples Park – Crestwood Gardens loop from Moorland

54.3 km

330 m

Moderate

Prison Stomp - Top of the climb – Middletown Cycling Shop loop from Hickory Hill

71.5 km

520 m

Moderate

Crestwood Gardens – Maples Park loop from Hickory Hill

54.3 km

290 m

Moderate

Crestwood Gardens loop from Moorland

44.1 km

240 m

Moderate

Maples Park – Crestwood Gardens loop from Worthington

106 km

830 m

Moderate

Sleepy Hollow Lake loop from Worthington

36.0 km

350 m

Moderate

Crestwood Gardens – Maples Park loop from Moorland

57.9 km

280 m

Moderate

Crestwood Gardens – Maples Park loop from Moorland

33.1 km

160 m

Easy

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1.

Prison Stomp - Top of the climb – Gathright Hill loop from Worthington

84.3km

03:56

640m

640m

The Prison Stomp - Top of the climb – Gathright Hill loop from Worthington is a demanding road cycling adventure that takes you through a mix of green spaces, urban fringes, and natural river corridors. You'll experience varied and undulating terrain, with the notable challenge of a significant climb up Gathright Hill. The route offers glimpses of the scenic Olentangy River and mature tree canopies, providing a diverse backdrop for your ride.

This moderate route covers 52.4 miles (84.3 km) with a substantial 2103 feet (641 metres) of elevation gain, typically requiring about 3 hours and 55 minutes to complete. It's designed for experienced road cyclists with good fitness levels who are looking for a serious workout. Be prepared for some unpaved segments that may test your bike handling skills.

As the most popular road cycling route in the Worthington Hills area, this loop is a draw for those seeking a substantial challenge. The region's network of trails, including connections to the Olentangy Greenway Trail, provides a comprehensive cycling environment. This route stands out for its challenging nature and highly rated status within the local cycling community.

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2.

Maples Park – Crestwood Gardens loop from Moorland

54.3km

02:37

330m

330m

The Maples Park – Crestwood Gardens loop from Moorland offers a delightful road cycling experience, winding through picturesque parklands and greenways. You'll enjoy varied scenery, including the namesake Maples Park with its mature trees and open fields, alongside glimpses of historic structures like the Dennis Deibel Barn. This route provides a refreshing escape into nature, with rolling hills and wooded sections creating a dynamic backdrop for your ride.

Planning your visit to this popular Maples Park Crestwood Gardens loop is straightforward, with access from the Moorland trail area in Crestwood. While specific parking information isn't detailed, the area is well-regarded for cycling, suggesting good local amenities. This moderate 33.8-mile (54.3 km) ride, with 1087 feet (331 metres) of elevation gain, takes approximately 2 hours and 36 minutes, making it a perfect half-day adventure for cyclists with good fitness.

This route stands out as the most popular road cycling route in the Crestwood area, highly rated by the Komoot community. Maples Park itself is a 22-acre community gem, featuring not only natural beauty but also amenities like picnic areas, a farm-themed playground, and a unique two-story limestone "tea house." It's a fantastic way to explore the scenic viewpoints on Crestwood Gardens cycling loop and the surrounding rural charm of Shelby County.

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3.

Prison Stomp - Top of the climb – Middletown Cycling Shop loop from Hickory Hill

71.5km

03:06

520m

520m

This road cycling loop, starting near Middletown Cycling Shop, offers a true taste of Louisville's varied terrain. You'll roll through a mix of urban and natural landscapes, encountering the region's signature rolling hills and some genuinely challenging climbs. Keep an eye out for parklands and creek-side paths, with the possibility of Ohio River waterfront views along the way. It's a route that rewards cyclists who appreciate diverse scenery and a good workout.

Planning your ride is straightforward, with Middletown Cycling Shop serving as a natural starting point and local cycling hub. While specific parking details for this exact route aren't widely published, the general area provides ample access. Be sure to pack plenty of water and nutrition for this 44.4 miles (71.5 km) journey, especially on warmer days. The route is rated moderate, with an estimated duration of 3 hours and 6 minutes, and includes 1699 feet (518 metres) of elevation gain.

Louisville's cycling scene is known for its

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5.

Crestwood Gardens loop from Moorland

44.1km

02:07

240m

240m

The Crestwood Gardens loop from Moorland offers a delightful road cycling experience, guiding you through a varied landscape of greenways, wooded sections, and expansive open vistas. You'll enjoy well-maintained paved surfaces as you navigate a mix of natural beauty and developed areas, making for a smooth and engaging ride. It's a route that truly showcases the diverse scenery of the Crestwood region, perfect for those who appreciate a blend of environments.

This moderate road cycling route covers 27.4 miles (44.1 km) with a manageable 775 feet (236 metres) of elevation gain, typically taking about 2 hours and 6 minutes to complete. While specific parking information isn't detailed, routes in this area are generally accessible. Be aware that a new shared-use path is under construction on Moorland Road, which will further improve safety and connectivity for cyclists.

Known for its popularity among local road cyclists, this loop is part of a highly-rated network of trails in the Crestwood area, often scoring around 4.7 stars on Komoot. The region's commitment to cycling is evident, with ongoing infrastructure improvements like the Moorland Road path, which will link to the Capital City Trail, enhancing the overall cycling experience.

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6.

Maples Park – Crestwood Gardens loop from Worthington

106km

04:59

830m

830m

The Maples Park – Crestwood Gardens loop offers a delightful road cycling journey through varied landscapes, including lush greenways and peaceful wooded sections. You'll pass by the historic Maples Park, a 22-acre greenspace with preserved farm buildings and a charming two-story limestone tea house, providing a scenic backdrop to your ride. The route's well-paved surfaces ensure a smooth experience, making it a favorite among local cyclists for its blend of natural beauty and historical interest.

This moderate road cycling route covers a substantial 66.0 miles (106.2 km) with an elevation gain of 2737 feet (834 metres), typically requiring about 4 hours and 58 minutes to complete. It's best suited for cyclists with a good level of fitness who are looking for a sustained ride with diverse scenery and some rolling hills. Plan to start early to make the most of the day and carry enough water and snacks for the duration.

What sets this route apart is the inclusion of Maples Park, which adds a unique cultural dimension to the ride. Beyond its historical structures, the park offers recreational amenities like a farm-themed playground and walking paths, making it a pleasant stop or a destination for family members not cycling. The route's popularity and high ratings within the Komoot community attest to its quality as a premier road cycling option in the area.

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8.

Crestwood Gardens – Maples Park loop from Moorland

57.9km

02:58

280m

280m

The Crestwood Gardens – Maples Park loop from Moorland offers a delightful road cycling experience, weaving through varied landscapes of greenways and wooded areas. You'll find mostly well-paved surfaces, making for a smooth ride, with the charming Maples Park serving as a key point of interest, featuring historical farm buildings and unique structures like a stone teahouse amidst abundant maple trees. This route provides a scenic journey for those looking to explore the natural features around Crestwood Gardens and Maples Park.

This moderate road cycling route covers 36.0 miles (57.9 km) with 923 feet (281 metres) of elevation gain, typically taking about 2 hours and 58 minutes to complete. It's best suited for cyclists with good fitness who appreciate a mix of terrain and some moderate elevation changes. Parking for Maples Park cycling is generally available, and checking the best time to cycle Crestwood Gardens Maples Park based on seasonal conditions will enhance your trip.

What sets this loop apart is its blend of natural beauty and historical significance, particularly around The Maples Park, which was once a small-scale farm. The route is highly rated by the cycling community, offering a peaceful environment for a break or a picnic. It's a fantastic option for those seeking best cycling routes near Maples Park that combine exercise with interesting landmarks.

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Tips from the Community

Jamie S.
January 23, 2024, Sleepy Hollow Lake

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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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.

0

0

Top of the climb called the Prison Stomp

0

0

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

0

0

Frequently Asked Questions

How many road cycling routes are available in Rolling Hills?

Rolling Hills offers a diverse selection of over 50 road cycling routes, catering to various skill levels and preferences. You'll find everything from easy rides to more challenging routes.

Are there easy road bike trails suitable for beginners in Rolling Hills?

Yes, Rolling Hills features 12 easy road cycling routes, perfect for beginners or those looking for a more relaxed ride. These routes typically have gentle ascents and descents, providing an accessible introduction to the region's undulating terrain.

What is the typical distance for road cycling routes in Rolling Hills?

The routes in Rolling Hills vary in distance, offering options for different endurance levels. For example, the Maples Park – Crestwood Gardens loop from Moorland is a moderate 33.8-mile (54.3 km) path, while the Prison Stomp - Top of the climb – Gathright Hill loop from Worthington extends to 52.3 miles (84.2 km).

Are there any advanced or challenging road cycling routes in Rolling Hills?

While most routes in Rolling Hills are moderate, there is one difficult road cycling route available for experienced riders seeking a greater challenge. The region's terrain is generally characterized by consistent elevation changes rather than extreme climbs.

What kind of landscape can I expect on road cycling routes in Rolling Hills?

Road cycling in Rolling Hills is defined by its undulating terrain, offering a mix of gentle ascents and descents through scenic countryside. You'll experience consistent elevation changes without extreme climbs, making for a varied and engaging ride.

What do other road cyclists enjoy most about the routes in Rolling Hills?

The road cycling routes in Rolling Hills are highly rated by the komoot community, with an average score of 4.8 stars from 8 reviews. Cyclists often praise the varied terrain, scenic countryside, and the network of roads that provide consistent, enjoyable elevation changes.

Are there loop road bike trails available in Rolling Hills?

Yes, many of the road cycling routes in Rolling Hills are designed as loops, allowing you to start and finish at the same point. Examples include the Crestwood Gardens – Maples Park loop from Hickory Hill and the Crestwood Gardens loop from Moorland.

What are some interesting landmarks or places to see near the road cycling routes?

While cycling, you might encounter various points of interest. Notable attractions in the wider Rolling Hills area include the historic Lewis and Clark Bridge and the picturesque Stone Arch Bridge in Seneca Park. You can also find natural features like the Crescent Hill Reservoir.

Are there any historical sites or trails to explore around Rolling Hills?

Yes, for those interested in history, the Brown Park Cemetery offers a glimpse into the past. Additionally, the Anchorage Trail provides another option for exploration, though it's not specifically a road cycling route.

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

Given the region's undulating terrain and consistent elevation changes, spring and autumn generally offer the most pleasant conditions for road biking in Rolling Hills. The weather is typically milder, and the natural scenery is vibrant, enhancing the cycling experience.

Are there any routes that pass through open countryside?

Many routes in Rolling Hills lead through open countryside, providing expansive views and a sense of freedom. The Prison Stomp - Top of the climb – Middletown Cycling Shop loop from Hickory Hill is a good example, guiding you through gentle hills and open landscapes.

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