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Road cycling routes
United States
Virginia
Loudoun County

Round Hill

The best road cycling routes around Round Hill

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437

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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.

Best road cycling routes around Roundโ€ฆ

Last updated: July 12, 2026

30

riders

#1.

Washington & Old Dominion Trail: Leesburg Loop

50.8km

02:10

310m

310m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

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. Mostly well-paved surfaces and easy to ride.

Moderate

5.0

(1)

4

riders

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Tips from the Community

Zachary
June 23, 2025, Washington & Old Dominion Regional Park

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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Picturesque gentle climb on the W&OD, a reminder that this was a railway for years and years

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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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Frequently Asked Questions

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

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.

How many road cycling routes are available in the Round Hill area?

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.

Are there any easy or beginner-friendly road cycling routes near Round Hill?

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.

What are the typical lengths and durations of road cycling routes in Round Hill?

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.

What do other cyclists say about road cycling in Round Hill?

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.

Are there any circular road cycling routes available?

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.

Where can I find parking for road cycling routes near Round Hill?

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.

What are some scenic viewpoints or landmarks I can see along the road cycling routes?

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.

Is public transport available to access road cycling routes in Round Hill?

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.

Are there any cafes or places to stop for refreshments along the road cycling routes?

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.

What is the best time of year for road cycling around Round Hill?

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.

Are there any advanced or challenging road cycling routes in the area?

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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