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Herndon Caboose Park โ Bridge to W&OD Trail Access loop from Sterling
19.5km
02:01
100m
100m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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By Fede from komoot
ยท
Updated May 30, 2026
If you've ever tried to plan jogging around Countryside, you know how quickly the options can feel overwhelming. With so many trails and paths, it's tough to tell which jogging routes are genuinely worth your time and effort, and which are just filler. That's where we come in. Our komoot community has mapped, run, and reviewed countless routes here, so we've done the legwork to bring you a curated shortlist of the very best, saving you the guesswork.
Jogging around Countryside is all about embracing a diverse natural environment. You'll find extensive trail networks winding through serene woodlands and expansive open fields, offering a refreshing escape from urban noise. The terrain varies from gentle inclines to more challenging hills (all under 650 feet or 200 meters), often alongside tranquil water features like lakes and rivers. Itโs a landscape that truly caters to all levels, from moderate loops to more demanding long-distance routes.
For a solid, challenging run that offers a real sense of accomplishment, we'd point you towards the Pavilion Lake โ Herndon Caboose Park loop from Ashburn. At 16.8 miles (27.1 km) with 475 feet (145 m) of elevation gain, itโs a difficult route that rewards your legs with varied scenery. If you're looking for something a bit quicker but still engaging, the Running loop from Ashburn is a fantastic moderate option at 5.5 miles (8.9 km). More than 600 runners have already explored Countryside with komoot โ ready to find your next favorite route?
Trail | Distance | Elevation | Difficulty |
|---|---|---|---|
| Herndon Caboose Park โ Bridge to W&OD Trail Access loop from Sterling | 19.5ย km | 100ย m | Hard |
| Pavilion Lake โ Herndon Caboose Park loop from Ashburn | 26.9ย km | 140ย m | Hard |
| Running loop from W&OD Trail Parking | 7.83ย km | 50ย m | Moderate |
| Herndon Caboose Park โ Herndon Town Hall loop from W&OD Trail Parking | 15.3ย km | 80ย m | Hard |
| Running loop from Amazon Web Services Datacenter Complex | 10.1ย km | 50ย m | Moderate |
| Cardinal Pond loop from Dulles Town Center | 5.85ย km | 20ย m | Moderate |
| Frogshackle Pond โ Little Flat Stairway loop from Sterling | 9.51ย km | 60ย m | Moderate |
| Running loop from University Center | 8.18ย km | 40ย m | Moderate |
| Running loop from Lowes Island | 7.58ย km | 50ย m | Moderate |
| Algonkian Regional Park โ Algonkian Regional Park loop from Lowes Island | 11.2ย km | 60ย m | Moderate |
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19.5km
02:01
100m
100m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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26.9km
02:47
140m
140m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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7.83km
00:49
50m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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15.3km
01:35
80m
80m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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10.1km
01:03
50m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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5.85km
00:36
20m
20m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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9.51km
01:09
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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8.18km
00:51
40m
40m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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7.58km
00:47
50m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
11.2km
01:10
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
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This library occupies a lovely, domed building, and is right next to the W&OD trail, which is friendly for both walkers and cyclists.
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A paved path winds all the way along the shore of the lake. Here you will find a gazebo on the end of a scenic jetty that runs out over the water by the Ashburn Village Sports Pavilion.
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The building that serves as the Herndon Depot Museum, also known as the Herndon Historical Society Museum, was built in 1875 to replace the original railway depot shed that was built in 1857. It was added to the National Register of Historic Places on June 18, 1979.
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The building that serves as Herndon Town Hall was built in 1939. It was the town's first official municipal building.
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Herndon Caboose Park is located in the heart of Herndon, VA, and is a small but historically significant park centered around a restored caboose from the Washington & Old Dominion (W&OD) Railroad. This vibrant red caboose serves as a nod to the townโs railway heritage and is a favorite spot for photos. There are a few benches and green spaces, as well as informational plaques about the areaโs railroading history. Situated along the popular W&OD Trail, itโs a popular rest stop for cyclists and walkers.
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All told, this converted rail trail runs for 45 miles through Virginia. The surface is a mix of pavement and crushed stone. You'll also find a good few bike shops along its length, offering bike rentals, repairs, and also beer, coffee, and snacks.
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The Washington and Old Dominion Trail and Regional Park, rich in history, spans 45 miles from Shirlington to Purcellville. Once a railroad line dating back to the 1850s, the trail now offers diverse scenery, transitioning from urban Arlington to suburban Falls Church and Vienna, and ending in rural Purcellville. Along the way, enjoy lush parks, tranquil streams, historical landmarks, and open farmland, making it an essential Virginia experience.
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Countryside offers a wide selection of over 70 running routes. These trails cater to various fitness levels, ranging from easy paths to more challenging long-distance options, ensuring there's something for every runner.
Yes, Countryside features 8 easy running routes perfect for beginners or those looking for a relaxed jog. The region's diverse landscape includes softer surfaces like forest trails and open fields, which are ideal for a comfortable running experience.
For experienced runners seeking a challenge, Countryside offers 8 difficult routes and 56 moderate trails. These include longer distances with varied inclines and declines, such as the Luck Stone Quarry Overlook โ Trailside Park loop from W&OD Trail Parking, which spans 11.8 miles, or the 13.8-mile Pavilion Lake loop from Ashburn, offering rolling hills and scenic views.
Many of the running routes in Countryside are designed as loops, providing convenient circular options. For example, the Running loop from Ashburn is a moderate 5.5-mile circular path, and the Cardinal Pond loop from Dulles Town Center offers a shorter 3.6-mile option around a tranquil water feature.
The running routes in Countryside offer diverse scenery. You can expect to encounter varied natural features like woodlands, open fields, and water features such as lakes and rivers. Some routes also pass by interesting landmarks, including the Luck Stone Quarry Overlook, providing scenic viewpoints.
While specific 'family-friendly' designations aren't always available, the region's easier and moderate routes, particularly those through open fields or around tranquil water features, can be suitable for families. Look for shorter, less challenging loops that offer pleasant scenery without significant elevation changes.
Many countryside trails are generally dog-friendly, especially those through woodlands and open spaces. It's always recommended to check specific trail regulations or local signage for any restrictions, but the extensive network of paths often welcomes well-behaved dogs on a leash.
Yes, several running routes in Countryside offer convenient parking. For instance, the challenging Luck Stone Quarry Overlook โ Trailside Park loop starts directly from the W&OD Trail Parking, making it easy to access by car.
The running experience in Countryside is highly rated by the komoot community, with an average score of 5.0 stars from 3 reviews. Runners often praise the diverse natural environment, the extensive trail networks, and the stimulating mix of woodlands, open fields, and varied inclines that make for an engaging outdoor activity.
Absolutely. Countryside's landscape includes numerous water features that enhance the running experience. The Pavilion Lake loop from Ashburn is a prime example, offering scenic views around a tranquil lake. Other routes may follow winding rivers or pass by babbling brooks, adding to the serene atmosphere.
The running trails in Countryside offer a varied terrain. You'll find softer surfaces in forests and woodlands, which are gentle on joints, as well as open fields providing expansive views. Many routes also feature uneven terrain with roots and rocks, which can help build stabilizing leg muscles and improve balance.


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