5.0
(4)
437
riders
16
rides
Road cycling routes around Round Hill traverse the rolling hills and rural landscapes of Loudoun County, Virginia. The region is characterized by agricultural lands, historic towns, and proximity to the Appalachian foothills, offering varied terrain for road cyclists. These routes often feature scenic country roads with moderate elevation changes, providing both challenging climbs and enjoyable descents. The area's network of roads connects to points of interest and offers views of the surrounding natural environment.
Last updated: July 12, 2026
30
riders
50.8km
02:10
310m
310m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
22
riders
73.5km
03:12
550m
550m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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9
riders
71.6km
03:07
610m
610m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
4
riders
56.4km
02:48
430m
430m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5
riders
34.2km
01:45
360m
360m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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The Washington & Old Dominion Trail and Bridal Path parallel one another as the trails run through a tunnel of green between Leesburg and Ashburn.
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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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Along this scenic, generally well-maintained gravel road is a large horse farm. Be on the lookout for the horses grazing as you ride past.
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This intersection can be busy, since it leads directly to WV cities of Charlestown, etc close to the west. The lovely church on the north of the roundabout often has unique food trucks and local ice cream from Moo Thru, a local dairy that produces simply amazing milk, cream, cheese, and ice cream!
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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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Road cycling routes around Round Hill, Virginia, are characterized by rolling hills and rural landscapes. You'll find varied terrain with moderate elevation changes, offering both challenging climbs and enjoyable descents through agricultural lands and historic areas. The region's proximity to the Appalachian foothills contributes to its diverse cycling environment.
There are over 15 road cycling routes available around Round Hill, catering to various skill levels. These include a mix of easy, moderate, and difficult options, ensuring there's a suitable ride for almost every road cyclist.
Yes, there are several easy routes suitable for beginners. For instance, the Washington & Old Dominion Trail: Leesburg Loop offers a relatively gentle ride, combining paved trail sections with local roads. Overall, about a quarter of the routes in the area are considered easy.
Route lengths vary significantly. For example, the popular Washington & Old Dominion Trail: Leesburg Loop is about 31.6 miles (50.8 km) and takes around 2 hours 10 minutes. Longer routes, like the Herndon Caboose Park โ Green Lizard Cycling, Herndon loop from Purcellville, can extend to over 50 miles (81 km) and take closer to 3 hours 20 minutes.
The road cycling routes around Round Hill are highly rated by the komoot community, with an average score of 4.8 stars from over 9 reviews. Over 600 road cyclists have used komoot to explore the area, often praising the scenic country roads and varied terrain.
Yes, many of the road cycling routes around Round Hill are designed as loops, allowing you to start and end at the same point. Examples include the Washington & Old Dominion Trail: Leesburg Loop and the Luck Stone Quarry Overlook โ Lovely Aldie loop from Purcellville, which offer scenic circular tours through the countryside.
Parking is generally available at various trailheads and public access points. For routes utilizing the W&OD Trail, you can often find parking in towns like Leesburg or Purcellville, such as near the Purcellville Train Station โ Washington & Old Dominion Trailhead. Many rural roads also offer safe shoulder parking, but always check local regulations.
The routes often pass through scenic countryside with views of agricultural lands and rolling hills. Notable viewpoints in the broader area include Bears Den Overlook and Raven Rocks Overlook, which offer expansive vistas. The region is also known for its proximity to the Appalachian Trail, providing a backdrop of natural beauty.
While direct public transport specifically for accessing rural road cycling routes might be limited, the W&OD Trail, which is incorporated into some routes like the Leesburg Loop, can be accessed from towns that may have local bus services. It's best to check specific transit options for towns like Leesburg or Purcellville if you plan to use public transport.
Yes, many routes pass through or near small towns and villages in Loudoun County, such as Purcellville and Aldie, where you can find cafes, pubs, and other establishments for refreshments. The W&OD Trail, in particular, has several towns along its length that offer amenities for cyclists.
The spring and fall seasons generally offer the most pleasant conditions for road cycling around Round Hill, with mild temperatures and beautiful scenery. Summer can be warm and humid, while winter may bring colder temperatures and potential for icy roads, though clear days can still be enjoyable.
Yes, for more experienced cyclists seeking a challenge, there are routes with greater elevation gains and longer distances. While most routes are moderate, some offer more demanding climbs through the rolling hills of Loudoun County. For example, the Luck Stone Quarry Overlook โ Lovely Aldie loop from Purcellville features significant elevation changes over its 44.5 miles.


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