4.5
(4)
145
riders
20
rides
Road cycling routes in Clarke County are set within the scenic Shenandoah Valley, at the foot of the Blue Ridge Mountains. The region features a mix of rolling hills, agricultural farmland, and views of the Shenandoah River. This landscape provides diverse terrain for road cyclists, ranging from gentle routes through open countryside to more challenging climbs in mountainous areas.
Last updated: October 10, 2026
3
riders
66.1km
03:01
550m
550m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
45
riders
89.8km
04:53
1,140m
1,140m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

12
riders
117km
05:50
1,550m
1,550m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
3.0
(1)
10
riders
53.5km
02:20
280m
280m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
32.6km
01:24
230m
230m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
11
riders
28.3km
01:16
160m
160m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(1)
4
riders
43.8km
02:47
290m
290m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(1)
5
riders
30.9km
01:22
210m
210m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
12
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
3
riders
30.2km
01:17
130m
130m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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No matter where you're going, or where you came from, it's all downhill from here. The road goes in three directions from here, so take your pick and enjoy the descent.
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Purcellville, at the end of the rail line, has great places to stop. Monk's BBQ is fantastic and easy, and if you want to simply spend more time you can take the distillery tour at the Catoctin Creek Distilling Company (makers of great rye and other spirits). They town has also kept the old downtown shopping area straight out of the 1940s, which is great to see.
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Goosecup is a coffee shop, located in Leesburg, VA. It is is a popular spot with locals and visitors alike and is known for its coffee and cozy atmosphere.
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The Sherando Park bike trails are a semi-newly constructed network of mountain biking trails. The paths are also open to foot traffic and are mostly beginner to intermediate in difficulty. There are some areas with bumpy terrain and some hills, but the trail network really is meant more for flowy loops than challenging climbs and technical terrain. The trails are also uni-directional for riding, so make sure to follow the direction arrows out on the paths.
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The stretch of the W&OD from Leesburg to Purcellville (~10 miles) is by far the best section.
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The Leesburg Quarry is a historical site right off the Washington & Old Dominion Trail. This paved multi-use trail is about 45 miles and is a great way to ride around the area free of cars. There is a historical marker right off the trail in front of the old quarry. In the 1860s, the railroad's arrival spawned businesses like the Leesburg Lime Company, operating here since 1868. Using dynamite, quarriers extracted limestone, later burned in kilns. The company supplied farmers with fertilizer and builders with plaster. Its decline came when bluestone from the eastern county proved more durable for roads.
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Clarke County offers a diverse network of 17 road cycling routes. These routes cater to various skill levels, from easy loops to challenging climbs, and have been explored by over 140 road cyclists using komoot.
Road cycling in Clarke County takes you through a variety of scenic landscapes. You'll experience routes at the foot of the Blue Ridge Mountains, alongside the picturesque Shenandoah River, and through extensive areas of gently rolling hills and beautiful agricultural farmland. This mix provides both serene countryside rides and more challenging mountainous sections.
Yes, Clarke County has several easy road cycling routes. For instance, the Roadbike loop from White Post is an easy 17.6-mile (28.4 km) trail through rolling farmland, typically completed in about 1 hour 16 minutes. Another easy option is the Roadbike loop from Shenandoah University, which covers 20.3 miles (32.6 km).
For experienced cyclists seeking a challenge, routes like the Turner Pond – Bluemont General Store loop from Snickers Gap offer significant elevation gain over 55.1 miles (88.7 km). Another demanding option is the Bluemont General Store loop from Snickers Gap, which extends to 64.9 miles (104.3 km) with substantial climbing.
The Shenandoah Valley region, including Clarke County, generally offers pleasant cycling conditions during spring, summer, and fall. Spring brings blooming landscapes, while fall showcases vibrant foliage. Summer is also popular, though it can be warmer. Winter cycling is possible, but weather conditions can vary, with colder temperatures and potential for snow or ice, especially in mountainous areas.
Yes, Clarke County is rich in history and natural beauty. Cyclists can explore sites such as the Cool Spring Battlefield, a significant Civil War site. The routes also offer views of the Shenandoah River and pass near the Bears Den Overlook, providing stunning panoramic views.
Many of the road cycling routes in Clarke County are designed as loops, offering convenient starting and ending points. Examples include the Berryville loop, the Roadbike loop from White Post, and the Roadbike loop from Winchester, among others.
The road cycling routes in Clarke County are highly rated by the komoot community, with an average score of 4.3 stars from over 3 reviews. Cyclists often praise the diverse terrain, scenic views of the Shenandoah River and Virginia countryside, and the variety of options available for different ability levels.
Absolutely. The Berryville route, a moderate 41.0-mile (66.1 km) loop, is particularly noted for its scenic views of the Shenandoah River and the surrounding Virginia countryside. Many other routes in the region will also offer glimpses or stretches along the river.
One of the longest road cycling routes in the area is the Bowers Hill loop from Shenandoah University, which spans 72.8 miles (117.2 km) and features significant elevation changes, making it a challenging and extended ride.
Yes, several road cycling routes are accessible from or near Winchester. The Roadbike loop from Winchester is a popular 19.2-mile (30.9 km) option, and the Bowers Hill loop from Winchester offers a longer 28.6-mile (46.0 km) ride.
Yes, Clarke County offers several routes of moderate difficulty. The Berryville route is a moderate 41.0-mile (66.1 km) loop, and the Sherando Park Bike Trails loop from Stephens City is another moderate option covering 33.3 miles (53.5 km).


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