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Road cycling routes
United States
Maryland
Washington County

Greensburg

The best road cycling routes around Greensburg

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Road cycling routes around Greensburg offer a diverse landscape, ranging from quiet road sections to dedicated rail trails. The region features varied terrain, providing a mix of climbing and descending opportunities for road cyclists. Greensburg serves as a gateway to the Laurel Highlands, characterized by its natural beauty and numerous parks. The area includes accessible trails like the Five Star Trail, built on an old trolley line, and offers scenic views of the city and surrounding natural features.

Best road cycling routes around Greensburg

  • The most popular road cycling route is Roadbike loop from Chewsville, a 26.1 miles (41.9 km) trail that takes 1 hour 55 minutes to complete. This moderate route features varied terrain suitable for a steady ride.
  • Another top favourite among local road cyclists is Roadbike loop from Williamsport, a moderate 62.0 miles (99.7 km) path. This longer route offers significant elevation changes and expansive views of the surrounding countryside.
  • Local road cyclists also love the Roddy Road Covered Bridge loop from Catoctin Mountain Park, a 19.7 miles (31.7 km) trail leading through scenic landscapes, often completed in about 1 hour 36 minutes.
  • Road cycling around Greensburg is defined by varied terrain, quiet road sections, and access to the natural beauty of the Laurel Highlands. The network offers options for different ability levels, from moderate loops to more challenging routes with significant elevation gain.
  • The guide includes highly-rated routes that showcase the best of the region's landscape. More than 10 road cyclists have used komoot to explore Greensburg's varied terrain.

Last updated: July 10, 2026

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#1.

Roadbike loop from Chewsville

41.9km

01:55

350m

350m

The Roadbike loop from Chewsville offers a rewarding journey through the varied terrain of Washington County, Maryland. You'll pedal past picturesque rural scenery, including rolling farmland and dense woodlands, with changing elevations providing expansive views of the Appalachian mountains. This moderate route, covering 26.1 miles (41.9 km) with 1160 feet (354 metres) of elevation gain, is a great option for cyclists seeking a good workout and quiet roads.

To plan your ride, consider starting from Chewsville, where you can typically find convenient access to the rural road network. The best seasons for this road cycling loop are spring, summer, and fall, when the weather is most favorable for exploring the region's hills and valleys. Always check local conditions before you go, as road surface quality can vary.

This area of Mountain Maryland is rich in history, with routes often traversing landscapes that tell stories of the past, including Civil War sites. While this specific loop focuses on road cycling, Chewsville's location also places it near major trail systems like the Western Maryland Rail Trail, offering alternative cycling experiences on paved paths.

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Moderate

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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. Some segments of this route may be unpaved and difficult to ride.

Moderate

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Hard

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Popular around Greensburg

Hiking around Greensburg

Tips from the Community

mtm05005
February 7, 2024, Stream and Wooden Bridge in Caledonia State Park

Caledonia State Park is a popular park near Gettysburg. There are miles of trails to choose from, as well as picnic areas and restrooms. The Appalachian Trail pass through the park, so there is a good chance you will see some hikers out enjoying the paths.

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This is one of many fire towers built in the forests of Pennsylvania. Big Flat Tower was built in 1921 by the Aermotor Windmill Company. It is located in Cumberland County in Michaux State Forest. It goes up to a height of 80 feet and is in good condition. It is a fire lookout tower that looks over the ever so famous town of Gettysburg.

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This historic wooden bridge was built in the mid-19th century to carry passengers across Owen's Creek. Although the smallest of the covered bridges in the county, it is no less beautiful.

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This beautiful bridge was built in 1856 and is still in use today: you can ride your bike over it and take the inevitable photo!

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Bonnie24
January 4, 2022, Conocheague Creek

Take a break in the wonderful, wildly romantic river with lots of benches

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Wonderful short trail along a creek and through rhododendron forests.

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The whole forest area is full of huge rhododendron bushes (maximum rhododendron according to the Flora incognita app)

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Frequently Asked Questions

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

Road cycling routes around Greensburg offer a diverse landscape with varied terrain. You'll find a mix of climbing and descending opportunities, as well as quiet road sections. The region serves as a gateway to the Laurel Highlands, providing scenic views and natural beauty.

Are there any long-distance road cycling routes available in the Greensburg area?

Yes, for those seeking a longer ride, the Greensburg area offers routes like the Roadbike loop from Williamsport. This moderate path spans nearly 100 km (62 miles) and features significant elevation changes, providing expansive views of the countryside.

What are some notable landmarks or natural features I might see while road cycling near Greensburg?

While cycling, you can explore the natural beauty of the Laurel Highlands. Specific highlights in the broader area include the scenic Cunningham Falls, the expansive High Rock Overlook, and the tranquil Catoctin Mountain Park. The Roddy Road Covered Bridge loop from Catoctin Mountain Park specifically leads through scenic landscapes.

Are there any challenging road cycling routes for experienced riders?

Yes, for advanced riders looking for a challenge, the Greensburg area includes routes like the Big Flat Tower loop from Waynesboro. This route is classified as difficult, covering over 91 km (56 miles) with significant elevation gain, offering a demanding experience.

What is the best time of year to go road cycling in Greensburg?

Greensburg generally experiences a temperate climate, making it conducive for outdoor activities like road cycling throughout much of the year. Spring and fall often offer pleasant temperatures and vibrant scenery, while summer can be enjoyable, though it's always wise to check local weather conditions.

Are there any paved trails suitable for road bikes in Greensburg?

Yes, the region features accessible trails like the Five Star Trail, which is built on an old trolley line and offers well-labeled bike lanes. While primarily a rail trail, its paved surface makes it suitable for road bikes, connecting Greensburg with several surrounding townships.

Where can I find parking for road cycling routes in Greensburg?

The Five Star Trail, a popular option for cyclists, has numerous parking areas conveniently located along its length, making it accessible for various ride lengths. For specific komoot routes, detailed parking information is often available on the individual tour pages.

Are there any moderate road cycling loops around Greensburg?

Yes, Greensburg offers several moderate road cycling loops. A popular choice is the Roadbike loop from Chewsville, a 42 km (26-mile) route with varied terrain suitable for a steady ride. Another moderate option is the Roddy Road Covered Bridge loop from Catoctin Mountain Park, which is about 32 km (20 miles).

What do other road cyclists say about the routes in Greensburg?

Road cyclists using komoot to explore Greensburg often praise the region's varied terrain, quiet road sections, and access to the natural beauty of the Laurel Highlands. The network of routes is appreciated for offering options suitable for different ability levels.

Can I find road cycling routes that offer scenic views of the city or natural landscapes?

Absolutely. Many routes in the Greensburg area provide scenic views. For instance, sections of the Five Star Trail offer views of the city, including the courthouse, particularly from overlooks above areas like Pittsburgh Street. Beyond the city, routes extend into the natural beauty of the Laurel Highlands, offering expansive countryside vistas.

Are there any parks near Greensburg that are good for cycling?

While not exclusively for road cycling, parks like Twin Lakes Park and Keystone State Park contribute to the area's outdoor appeal. Keystone State Park, for example, offers designated bike trails, including a 2-mile loop around its lake, which can be a pleasant addition to a road cycling trip or a destination for a more relaxed ride.

How many road cycling routes are featured in the Greensburg guide?

The Greensburg guide features four highly-rated road cycling routes, showcasing the best of the region's diverse landscape. These routes range from moderate loops to more challenging options with significant elevation gain.

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