32
runners
13
runs
Jogging around Pawling, New York, offers diverse landscapes for outdoor enthusiasts. The region is characterized by extensive trail networks, including sections of the Appalachian Trail and the Maybrook Trailway. Runners can explore deciduous forests, wetlands, and open fields, with routes often featuring streams, ponds, and scenic views of the Harlem Valley. The terrain includes gentle gradients along converted railway lines and more varied paths within nature reserves.
Last updated: May 17, 2026
4
runners
8.47km
00:53
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
runners
9.15km
00:58
80m
80m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Sign up for free
3
runners
8.10km
00:51
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
7
runners
10.1km
01:03
50m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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 Pawling
This paved rail trail traverses two counties in New York — you can bike more than 28 miles on it if you go from end to end. This particular section passes through a sort of wetland land — keep an eye out for birds!
0
0
It's along the rail trail. No fishing and no swimming from the trail side.
0
0
Whaley Lake is the largest lake in Dutchess County. So nice to ride here!
0
0
Whaley Lake is the largest lake in Dutchess County. So nice to ride here!
1
0
There are 10 dedicated jogging routes around Pawling available on komoot, catering to various preferences and fitness levels. These include routes ranging from easy to challenging.
Pawling offers a diverse range of terrains for runners. You'll find relatively flat, paved surfaces along the Maybrook Trailway, ideal for a smoother experience. Other routes, particularly within the Appalachian Trail sections and the Pawling Nature Reserve, feature more varied paths through deciduous forests, wetlands, and open fields, with some elevation changes and natural surfaces.
Yes, Pawling offers routes suitable for beginners. While most routes are moderate, you can find paths with gentle gradients, especially along converted railway lines like sections of the Maybrook Trailway. These provide a good starting point for those new to jogging or looking for a less strenuous run.
Jogging in Pawling offers many scenic rewards. You can enjoy picturesque views of the Harlem Valley region, especially from trails within the Pawling Nature Reserve. The Appalachian Trail section includes a unique 1,600-foot boardwalk across the Great Swamp, offering wildlife viewing. Additionally, routes like Spring Lake loop from Sherman and Whaley Lake – Whaley Lake loop from Holmes provide beautiful lakeside vistas.
Yes, for longer runs, the Maybrook Trailway is an excellent choice. As part of the larger Empire State Trail, it offers extended possibilities for continuous running. Additionally, sections of the Appalachian Trail through Pawling provide miles of scenic terrain that can be combined for longer distances.
Yes, many of the jogging routes in Pawling are designed as loops. For example, the Running loop from Appalachian Trail, Spring Lake loop from Town Meadows, and Running loop from Village of Pawling are all circular paths, allowing you to start and end at the same point without retracing your steps.
Pawling's trails are enjoyable throughout the year, but spring and fall offer particularly pleasant conditions with mild temperatures and vibrant natural scenery. Spring brings active small waterfalls and lush greenery, while fall showcases stunning foliage. Summer can be warm, so early morning or late afternoon runs are recommended. Winter jogging is also possible, though some trails may require appropriate gear for snow or ice.
Many trails in the Pawling area, including sections of the Appalachian Trail and trails within the Pawling Nature Reserve, are generally dog-friendly. However, it's always recommended to keep dogs on a leash and to check specific trail regulations before heading out to ensure a safe and enjoyable experience for everyone.
Beyond the trails themselves, you can find several points of interest. The Pawling Nature Reserve offers impressive gorges and diverse habitats. The Maybrook Trailway is a landmark in itself as a converted railway line. You might also encounter Whaley Lake or wetlands along the Maybrook Trailway, providing scenic backdrops for your run.
Runners frequently praise the diverse landscapes and the peaceful, natural environment of Pawling. The blend of well-maintained trails, including sections of the Appalachian Trail and the Maybrook Trailway, offers variety for all skill levels. Many appreciate the scenic views of the Harlem Valley, the presence of lakes like Spring Lake and Whaley Lake, and the opportunity for wildlife viewing, making for a refreshing escape.
Yes, the Metro-North Railroad's Harlem Line has a station in Pawling, offering access to the area. A significant section of the Appalachian Trail, for instance, can be accessed directly from the Metro-North AT Train Station on Route 22, making it convenient for those relying on public transportation.
The Pawling Nature Reserve features streams, ponds, and small waterfalls, which are particularly active and impressive in the spring. While specific jogging routes might not be centered around a single large waterfall, exploring the trails within the reserve during the wetter seasons will likely offer views of these natural water features.


Browse the best Running Trails & Routes in other regions.