4.7
(4)
214
riders
16
rides
Road cycling routes around The Plains, Virginia, traverse a landscape characterized by rolling hills and extensive farmland, offering scenic vistas. The region is situated between the Blue Ridge and Bull Run Mountains, providing a backdrop of distant mountain views. This area is known for its equestrian heritage, with many farms and estates contributing to the rural charm. The terrain includes both gentle gradients and challenging climbs, catering to varied road cycling preferences.
Last updated: August 11, 2026
14
riders
35.3km
01:43
310m
310m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
13
riders
129km
06:50
1,830m
1,830m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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12
riders
68.9km
03:42
640m
640m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
9
riders
72.1km
03:58
750m
750m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(1)
6
riders
71.2km
03:56
760m
760m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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Popular around The Plains
Beautiful fun town with nice places to stop and eat. A couple of gas stations with easy Gatorade if you need to top off, or places to stop and grab lunch if you have more time
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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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Nice gravel along a shady road. The road has some slight rollers, but nothing too difficult, so it is a nice road for a relaxed ride.
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Turning off Crest Hill Rd, hard climb with 14 or 15% grade followed 2 more moderate climbs. The first won't show on the Garmin because it's too short - but it can hurt! Rural roads are poor but beautiful
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This pond provides a very peaceful atmosphere with great views of the water and rolling hills in the background. The park has designated this pond as its official Dark Sky Observation Area.
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The historic district of Middleburg is absolutely beautiful and offers several historic building dating back to the 1800s. There are some nice inns and shops to visit. The 'Red Fox Inn and Tavern' claims to be the oldest original guesthouse of the US.
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There are over 15 road cycling routes around The Plains, offering a variety of experiences for different skill levels. You'll find a mix of moderate and difficult routes to explore.
Road cycling around The Plains is characterized by a beautiful landscape of rolling hills and extensive farmland. You can expect scenic vistas, distant mountain views from the Blue Ridge and Bull Run Mountains, and routes that include both gentle gradients and challenging climbs. Some areas feature historic gravel roads, though the focus here is on paved road cycling.
Yes, while the area offers challenging terrain, there are moderate routes available. For example, the Roadbike loop from The Plains is a moderate 21.9-mile trail that takes you through local rolling hills, often completed in under two hours.
For experienced cyclists seeking a challenge, routes like the Bluemont General Store – Turner Pond loop from Marshall offer significant elevation changes over 55 miles. Another demanding option is the Blue Ridge Mountains loop from Marshall Middle School, which covers over 80 miles with substantial climbs, providing a true test of endurance.
As you cycle, you'll be treated to picturesque views of rolling hills, expansive farmland, and the distant Blue Ridge and Bull Run Mountains. The region is also known for its equestrian heritage, so you'll often pass by beautiful horse farms and estates. Nearby attractions include the Great Meadow, a large open-air facility, and Sky Meadows State Park, which offers scenic views and trails.
Yes, parking is generally available in and around The Plains. Many routes start from towns like Marshall or directly from The Plains, where you can find suitable parking options to begin your ride.
Public transportation options directly to the starting points of many road cycling routes in The Plains are limited. The area is primarily rural, making personal vehicle transport the most convenient way to access the trails.
Generally, no special permits are required for road cycling on public roads around The Plains. However, if you plan to cycle through any private properties or participate in organized events, it's always best to check specific requirements for those instances.
The spring and fall seasons are generally considered the best times for road cycling in The Plains. The weather is typically mild and pleasant, and the scenery is particularly beautiful with spring blooms or autumn foliage. Summer can be warm and humid, while winter may bring colder temperatures and potential for icy conditions.
While many routes in the area involve significant distances and elevation changes, some moderate loops through rolling hills might be suitable for families with older, experienced children. Always review the route details, including distance and elevation, to ensure it matches your family's cycling ability.
Road cycling, especially on open roads with traffic, is generally not recommended for cycling with dogs due to safety concerns for both the rider and the animal. For activities with dogs, nearby Sky Meadows State Park offers trails where leashed dogs are permitted.
The road cycling routes in The Plains are highly rated by the komoot community, with an average score of 4.5 stars. Cyclists often praise the stunning rural scenery, the challenging yet rewarding climbs, and the peaceful experience of riding through horse country and farmlands.
Yes, many of the road cycling routes around The Plains are designed as loops, allowing you to start and end your ride in the same location. Examples include the Lake Willow Bike Path – Lake Brittle loop from Arlington Outdoor Lab and the Roadbike loop from The Plains.


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