5.0
(4)
22
riders
7
rides
Road cycling routes around Penn feature a diverse landscape, offering a mix of rolling hills, river valleys, and forested areas. The region's topography provides varied terrain suitable for different skill levels, from gentle paths to more challenging ascents. Cyclists can expect routes that traverse natural settings and connect to local points of interest. The area is characterized by its network of roads that wind through both developed and natural environments.
Last updated: May 17, 2026
6
riders
30.0km
01:35
270m
270m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4
riders
27.5km
01:29
220m
220m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

Sign up for free
2
riders
38.0km
02:01
430m
430m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
2
riders
52.1km
02:38
640m
640m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(4)
2
riders
19.3km
01:06
230m
230m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
Greensburg is a historic city in Westmoreland County. It was first settled at the end of the 18th century and became an important city in the area when coal was discovered nearby. Now, the city still has a vibrant commercial area, with restaurants and shops, so it is a good place to stop on the Five Star Trail.
0
0
The Five Star Trail connects Greensburg to Youngwood via a converted railway. This multi-use trail is flat and wide and is a great way to explore the area at your own pace.
0
0
Nice view of Turtle Creek. The Westmoreland Heritage Trail follows the creek, so there are several good spots to see the creek. The trail crosses the creek via a bridge at this point, so it is an especially good viewing spot.
0
0
Greensburg is a historic city in Westmoreland County. It was first settled at the end of the 18th century and became an important city in the area when coal was discovered nearby. Now, the city still has a vibrant commercial area, with restaurants and shops, so it is a good place to stop on the Five Star Trail.
1
0
The Five Star Trail is a rail-with-trail that runs from Greensburg to Youngwood. The trail is flat, so it is not a challenging route. For a lot of the trail, it runs next to the Southwestern Pennsylvania Railroad corridor.
0
0
If you head here from the 5 star and then down Pavilion Lane you will come out across the street from Delaneys and the shopping center
0
0
There are 7 road cycling routes around Penn, offering a variety of experiences for different skill levels. You'll find 2 easy routes and 5 moderate routes to explore.
Pennsylvania offers excellent road cycling from spring through fall. The state's diverse landscapes, from the rolling hills of the Pocono Mountains to the challenging Allegheny hills, are particularly beautiful during these seasons. While some areas might be accessible in winter, many trails and roads can be affected by snow and ice.
Yes, there are a couple of easy road cycling routes. For a gentle ride, consider the Greensburg – Greensburg loop from Greensburg, which covers about 30 kilometers with minimal elevation gain. Pennsylvania's extensive network of rail trails, like the Pine Creek Rail Trail (often called the "Grand Canyon of Pennsylvania"), are also generally flat and family-friendly, though not all are directly in the immediate Penn area.
The region around Penn, and Pennsylvania in general, offers varied terrain. You can expect a mix of rolling hills, some steeper climbs, and flatter sections, especially along repurposed rail trails. Routes like the Five Star Trail – Greensburg loop from Greensburg feature moderate elevation changes, providing a good workout without being overly strenuous.
Yes, many of the routes around Penn are designed as loops. For example, the Five Star Trail – Five Star Trail loop from Greensburg offers a moderate 27.5-kilometer circular ride. Another option is the Turtle Creek loop from Ardara, which is a moderate 19.2-kilometer circuit.
The komoot community highly rates the road cycling experiences around Penn, with an average score of 5.0 stars based on 4 reviews. Cyclists often praise the scenic beauty and the variety of routes available, from leisurely loops to more challenging rides.
While the immediate Penn area routes listed here are mostly easy to moderate, Pennsylvania as a state offers significant challenges. Regions like the Laurel Highlands are renowned for their steep climbs and low-traffic roads, appealing to experienced road cyclists seeking substantial elevation gains. For example, Pavia Road in Blue Knob State Park is known as one of Pennsylvania's most difficult bike climbs.
Many road cycling routes in Pennsylvania, including those near Penn, often follow river valleys or pass through forested areas, offering picturesque views. The state is rich in natural beauty, with thousands of miles of rivers and streams, and extensive forests. While specific viewpoints aren't detailed for every route, the overall experience is enhanced by the natural surroundings.
Absolutely. Pennsylvania's cycling routes frequently wind through historically significant areas. Many rail trails, for instance, showcase the state's industrial heritage. Additionally, some routes, particularly in broader Pennsylvania, offer glimpses into unique cultural enclaves like Amish country, enriching your ride with historical and cultural immersion.
For broader information on outdoor adventures and biking opportunities across Pennsylvania, you can visit the official tourism websites. Check out visitpa.com for general outdoor activities or their biking-specific page for more details on cycling throughout the state.
The longest route currently listed around Penn is the Greensburg – Greensburg loop from Greensburg, which spans approximately 52.7 kilometers and is rated as moderate difficulty.


Browse the best Road cycling routes in other regions.