26
runners
7
runs
Jogging around Upperville offers a varied landscape for runners, featuring rolling hills, open pastures, and dense woodlands. The region includes expansive areas like Sky Meadows State Park, which provides a network of trails for different fitness levels. Jogging routes often pass through scenic areas with panoramic views of the Piedmont region. This diverse terrain makes Upperville suitable for both leisurely jogs and more challenging trail runs.
Last updated: June 24, 2026
5
runners
6.53km
00:51
150m
150m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
runners
5.07km
00:37
80m
80m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5
runners
5.12km
00:37
80m
80m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
runners
28.1km
04:00
1,090m
1,090m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
runners
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Upperville
Nice place for a picnic or just relaxing on the grass.
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A brief yet steep hike for panoramic views of Virginia's Piedmont region. The Upper Piedmont Overlook unveils a protected Eastern U.S. landscape. Wear sturdy, mud-friendly shoes for this occasionally slippery part of the trail.
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The Lower Piedmont Overlook is one of a few official viewpoints along the Piedmont Overlook hiking loop. There are open views of the valley, pastures, and surrounding meadow.
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There is a small waterfall here off the side of the trail. There is no sign marking where to turn, but you can literally hear and see the water from the side of the trail if the current is strong enough. The best time to see the falls in full force is right after a big rain.
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Buzzard Hill is one of many lower summits you can hit while hiking this section of the Appalachian Trail. The summit only reaches up to 1,301 feet, but it's higher than many of the surrounding foothills, so you get a pretty good view down into the valley from the lookout area. No matter which direction you come from, be prepared for a hilly hike both during your approach and your return.
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There are over 9 running routes documented on komoot for the Upperville area. These routes offer a diverse range of experiences, from easier jogs to challenging trail runs, catering to various fitness levels.
Yes, Upperville offers routes suitable for beginners. While many trails feature rolling hills, there are options with less elevation gain. For instance, the Running loop from Sky Meadows State Park is a moderate 4-mile trail that provides a pleasant experience without extreme difficulty. Sky Meadows State Park itself has a network of trails, some of which are less strenuous.
For those seeking a challenge, Upperville's terrain with its significant elevation changes is ideal. The Waterfall – Buzzard Hill viewpoint loop from Ashby Gap is a difficult 17.5-mile route with substantial climbs and descents. Another demanding option is the Lower Piedmont Overlook – Upper Piedmont Overlook loop from Ashby Gap, a difficult 9.2-mile path offering panoramic views after significant climbs.
Yes, many of the popular running routes around Upperville are circular, allowing you to start and end at the same point. Examples include the Running loop from Sky Meadows State Park and the Lower Piedmont Overlook – Upper Piedmont Overlook loop from Ashby Gap, both offering scenic loops through the region's diverse landscape.
Upperville's running routes are rich with natural beauty and scenic viewpoints. You can expect to encounter rolling hills, open pastures, and dense woodlands. Notable features include the Sky Meadows State Park itself, offering diverse trails. Many routes lead to stunning vistas like the Upper Piedmont Overlook, providing panoramic views of Virginia's Piedmont region. The Buzzard Hill viewpoint also offers impressive views and, after rain, a potential waterfall.
Many outdoor areas in Upperville, including Sky Meadows State Park, generally welcome dogs on trails, provided they are kept on a leash. However, specific policies can vary, especially in certain sections or during particular seasons. It's always recommended to check the latest regulations for individual parks or trails before heading out with your dog.
Yes, many popular running routes and parks in the Upperville area, such as Sky Meadows State Park, offer designated parking facilities. For routes starting from Ashby Gap, there are usually accessible parking options nearby. It's advisable to check the specific route details on komoot for precise parking information.
Upperville offers beautiful running conditions throughout much of the year. Spring and fall are particularly popular due to mild temperatures and vibrant foliage. Summer can be warm and humid, so early morning or late afternoon runs are often preferred. Winter running is possible, but trails may be affected by snow or ice, especially on higher elevations, so checking conditions beforehand is recommended.
While not always guaranteed, the Buzzard Hill area, accessible via routes like the Waterfall – Buzzard Hill viewpoint loop from Ashby Gap, is known to have a small waterfall, particularly vibrant after periods of rain. This adds an extra scenic element to an already challenging and rewarding run.
Runners frequently praise Upperville for its diverse and picturesque landscape. The rolling hills, open meadows, and wooded paths provide a constantly changing backdrop. The panoramic views from overlooks like the Piedmont Overlooks and Buzzard Hill are often highlighted as rewarding features after a good climb. The variety of trails, from moderate to difficult, also means there's something for every fitness level.
While popular spots like Sky Meadows State Park can see more visitors, exploring some of the scenic gravel roads in the Upperville area can offer a quieter running experience. These roads often wind through tranquil woodlands and along streams, providing a different kind of terrain and a peaceful atmosphere away from the main trails. Komoot's route suggestions can help you discover these less-traveled paths.


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