25
runners
3
runs
If you've ever tried planning your next run, you know how overwhelming it can be to find the truly great jogging routes around Pomfret. With so many trails out there, it's tough to tell which ones are genuinely worth your time and effort, and which are just filler. That's where we come in. Our komoot community has hit the trails, mapped, and reviewed the best of Pomfret, so we've curated a shortlist of routes that are absolutely worth your legs.
Jogging in Pomfret means immersing yourself in "The Last Green Valley," a region defined by its unspoiled rural character, rolling hills, and dense forests. You'll find a fantastic mix of terrain, from the relatively flat, former railway beds of the Air Line State Park Trail to more challenging paths winding through Mashamoquet Brook State Park. This area offers a great range for all abilities, whether you're looking for an easy loop or a longer, more demanding run.
If you only do one route, we'd point you to the Indian Head Rail Trail loop from White Plains. It's a moderate 3.3 miles (5.4 km) that follows a former railway bed, making it wonderfully accessible and generally flat – perfect for a consistent pace. For those ready to stretch their legs a bit more, the Running loop from Waldorf offers a more challenging 9.5 miles (15.3 km) through varied terrain. Dive into these routes and more, and see why over 25 runners have already explored Pomfret with komoot.
Last updated: June 6, 2026
9
runners
5.37km
00:33
10m
10m
The Indian Head Rail Trail loop from White Plains offers a serene escape into nature, perfect for a refreshing jog. You'll follow a smooth, paved path that meanders through lush mature forests and extensive wetlands, providing a unique opportunity to spot local wildlife like deer and various bird species. The trail's flat terrain, built on an old railroad bed, makes for an incredibly easy and consistent running experience.
Planning your visit is straightforward, with convenient parking available at the White Plains trailhead. The trail is well-maintained and features amenities such as benches and occasional restrooms, ensuring a comfortable outing. While it's a great option any time, consider visiting in the spring or fall for the most comfortable temperatures and vibrant scenery.
This 3.3-mile (5.4 km) loop, with a negligible 34 feet (10 metres) of elevation gain, is rated moderate and takes about 33 minutes to complete. Its origin as a former railroad line, used to supply the Navy's Indian Head Powder Factory, adds a touch of history, with a train caboose at the eastern trailhead in White Plains serving as a nod to its past. It's an excellent choice for beginner joggers or anyone seeking a peaceful, accessible outdoor activity.
5
runners
10.0km
01:02
40m
40m
The Running loop from Westlake High School offers a consistent and accessible jogging experience, ideal for a steady workout. This route, likely featuring well-maintained surfaces around the school and local area, provides a straightforward path for runners. With a moderate difficulty and minimal elevation changes, it's a good option for those who prefer a predictable environment for their daily run, free from the challenges of technical trails.
Planning your visit to this loop is generally simple, with parking typically available in the vicinity of Westlake High School or nearby streets. It's always a good idea to check for any local restrictions or school events that might affect access, especially if you plan to run during school hours. Early mornings or evenings are often the best times to enjoy the route with fewer people and more comfortable temperatures.
While specific natural features are not highlighted for this particular loop, its urban-adjacent setting means you'll likely encounter a blend of residential and perhaps some green spaces. The route's primary appeal lies in its convenience and suitability for regular exercise, making it a practical choice for local joggers in the Waldorf, Maryland area. It serves as a reliable option for maintaining fitness without needing to travel to more remote trailheads.

Sign up for free
3
runners
15.3km
01:35
50m
50m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
runners
13.6km
01:25
50m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
runners
10.8km
01:07
40m
40m
Lace up your shoes for a proper cross country experience on the North Point High School jogging trails. This moderate 6.7-mile (10.8 km) loop, which takes about 1 hour and 6 minutes to complete, offers a genuine feel of a certified course, with its uneven terrain of dirt and grass. You'll find yourself navigating natural surfaces, including winding through the dark woods behind the school, making it a great spot for focused training.
Parking for running North Point High School loop is typically available on the school grounds, making trailhead access convenient. Given the outdoor conditions, plan your visit according to seasonal running conditions in Charles County, Maryland; early mornings or evenings are often best during warmer months. Remember to bring water, especially if you're tackling this 140 feet (43 metres) of elevation gain on a hot day.
This route is primarily known as an official cross country course, certified for 5K events, providing a consistent and reliable running environment. While it doesn't boast dramatic vistas, it offers a solid workout on varied ground. For those seeking more diverse scenery, Charles County also features other trails in parks like Mallows Bay Park and Gilbert Run Park, known for their natural landscapes.
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 Pomfret
Perfect asphalt surface, a beautiful route for the family. On some sunny Sundays it can be more crowded, but it is usually a quiet and sparsely populated trail.
0
0
Komoot features several running routes around Pomfret. Currently, you can explore five distinct routes, offering a variety of distances and experiences for joggers of all levels.
Pomfret's jogging trails offer diverse terrain, from the relatively flat, accessible surface of the Air Line State Park Trail, ideal for easy runs, to the varied landscapes within Mashamoquet Brook State Park, which include dense forests, rocky ledges, and scenic brook valleys. You'll find a mix of well-maintained paths and more natural, unpaved trails.
Yes, Pomfret offers great options for families. The Air Line State Park Trail, with its flat former railway bed, is excellent for a leisurely run or walk with children. Additionally, Pomfret Recreation Park provides well-maintained trails in a serene setting, suitable for family outings. Mashamoquet Brook State Park also has trails that can be enjoyed by families, though some sections may be more challenging.
Many trails in Pomfret are dog-friendly, provided your pet is on a leash. Areas like Mashamoquet Brook State Park and the Air Line State Park Trail are popular choices for runners with dogs. Always check local regulations for specific trails, but generally, Pomfret welcomes leashed dogs on its outdoor paths.
While jogging in Pomfret, you can encounter several points of interest. The historic Wolf Den is located within Mashamoquet Brook State Park, offering a unique historical stop. The Indian Head Rail Trail itself is a notable feature, providing scenic views. You might also pass through areas like Myrtle Grove or the Mattawoman Natural Environment Area, known for their natural beauty.
Yes, komoot features several circular running routes in the Pomfret area. For example, you can try the Indian Head Rail Trail loop from White Plains, which offers a moderate 5.3 km circuit. Other loops, such as the Running loop from Westlake High School, provide longer distances for those seeking more extensive circular runs.
Pomfret is beautiful for jogging year-round, but spring and fall offer particularly pleasant conditions with mild temperatures and vibrant foliage. Summer mornings and evenings are also great to avoid the midday heat. Winter running is possible, especially on well-maintained trails like the Air Line Trail, but be mindful of snow and ice conditions.
The running routes around Pomfret vary in difficulty. Most routes are classified as moderate, such as the Running loop from North Point High School (13.6 km) or the Running loop from North Point High School (10.7 km). There is also a more challenging option, the Running loop from Waldorf, which covers over 15 km.
Absolutely. For those looking for longer runs, the Air Line State Park Trail offers extensive stretches, being Connecticut's longest multi-town trail. You can also find specific routes like the Running loop from Waldorf, which is over 15 km, or the Running loop from North Point High School, at 13.6 km, providing ample distance for endurance training.
Parking is generally available at key access points for popular jogging areas. For instance, Mashamoquet Brook State Park has designated parking facilities. The Air Line State Park Trail often has parking near its various access points, including near the Pomfret Town Hall. Pomfret Recreation Park also provides parking for visitors.
While Pomfret is a rural area, public transport options might be limited directly to trailheads. It's advisable to check local bus schedules or ride-sharing services for connections to the general Pomfret area. However, for direct access to many trails, personal vehicles are often the most convenient option.


Browse the best Running Trails & Routes in other regions.