Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Running Trails
United States
Virginia
Fauquier County

Upperville

The best running trails around Upperville

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.

Best jogging routes around Upperville

  • The most popular jogging route is Waterfall – Buzzard…

Last updated: June 24, 2026

5

runners

#1.

Bridle Overlook loop from Sky Meadows State Park

6.53km

00:51

150m

150m

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate with device

Send to Phone

Save

Moderate

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
Sign up for free to see 3 more runs around Upperville.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Upperville

Hiking around Upperville

Tips from the Community

Freelancer 🥾 🚵 🏍️🏃‍♂️
January 21, 2025, Lower Piedmont Overlook

Nice place for a picnic or just relaxing on the grass.

Translated by Google

1

0

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.

0

0

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.

0

0

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.

0

0

Matthew
September 27, 2023, View from Buzzard Hill

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.

0

0

Frequently Asked Questions

How many running routes are available around Upperville?

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.

Are there running routes suitable for beginners or those seeking an easier jog in Upperville?

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.

What kind of challenging running trails can I find near Upperville?

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.

Are there any circular running routes in the Upperville area?

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.

What natural features or landmarks can I expect to see along the running routes?

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.

Are the running trails in Upperville dog-friendly?

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.

Is there parking available at the trailheads for running routes in Upperville?

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.

What is the best time of year to go running in Upperville?

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.

Can I find routes that feature waterfalls in the Upperville area?

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.

What do other runners enjoy most about jogging in Upperville?

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.

Are there any hidden gem running routes in Upperville that are less crowded?

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.

Most popular routes around Upperville

Hiking around Upperville

Most popular attractions around Upperville

Places to see

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Explore more

Browse the best Running Trails & Routes in other regions.

New BaltimoreParisSky Meadows State Park

Nearby adventure guides

Things to Do around Paris

background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy