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Routes
Running Trails
United States
New York
Dutchess County

Pawling

The best running trails around Pawling

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.

Best jogging routes around Pawling

  • The most popular jogging route is Running loop…

Last updated: May 17, 2026

4

runners

#1.

Running loop from Appalachian Trail

8.47km

00:53

60m

60m

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

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Moderate

3

runners

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

Moderate
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3

runners

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

Moderate

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

Moderate
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Popular around Pawling

Hiking around Pawling

Road Cycling Routes around Pawling

Cycling around Pawling

Tips from the Community

Lisa
September 28, 2024, Wetlands Along Maybrook Trailway

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!

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Buck R-T
July 10, 2022, Whaley Lake

It's along the rail trail. No fishing and no swimming from the trail side.

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Whaley Lake is the largest lake in Dutchess County. So nice to ride here!

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Whaley Lake is the largest lake in Dutchess County. So nice to ride here!

1

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Frequently Asked Questions

How many running routes are available in Pawling?

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.

What kind of terrain can I expect on jogging trails in Pawling?

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.

Are there any easy or beginner-friendly jogging routes in the Pawling area?

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.

What are some scenic viewpoints or natural features to look out for on Pawling's running trails?

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.

Are there any long-distance running options around Pawling?

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.

Are there any circular running routes in Pawling?

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.

What are the best times of year to go jogging in Pawling?

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.

Are there any dog-friendly running trails in Pawling?

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.

What are some notable landmarks or points of interest near the jogging routes?

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.

What do other runners enjoy most about jogging in Pawling?

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.

Is there public transport access to jogging trails in Pawling?

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.

Are there any routes that feature waterfalls?

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.

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