Pawling is a region in New York known for its diverse landscapes, offering a variety of outdoor activities. Nestled in the foothills of the Berkshires, the area features significant natural landmarks such as portions of the Appalachian Trail, the expansive Great Swamp, and the Maybrook Trailway. These features provide a scenic and varied backdrop for several sports like hiking, road cycling, touring cycling, and jogging.
For those seeking outdoor activities, Pawling provides more than 10…
39
Routes
4.9
(32)
Average rating
468
People visited

2
hikers
5.87km
01:37
100m
90m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

5.0
(1)
1
hikers
14.9km
03:49
40m
110m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

1
hikers
3.84km
01:05
80m
80m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

7.30km
02:10
270m
100m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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5.0
(8)
137
riders
103km
04:17
620m
620m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

5.0
(1)
72
riders
46.2km
01:54
250m
250m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

9
riders
64.5km
02:55
640m
640m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

12
riders
19.0km
00:49
90m
90m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
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4.5
(8)
67
riders
105km
06:13
650m
650m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(7)
28
riders
48.0km
02:47
270m
270m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(1)
14
riders
25.7km
01:31
160m
160m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4.8
(4)
20
riders
42.7km
02:30
210m
210m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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4
runners
8.47km
00:53
60m
70m
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.

3
runners
8.10km
00:51
70m
70m
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.
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Pawling offers diverse outdoor activities including hiking, road cycling, touring cycling, and jogging. The region features varied landscapes such as the Appalachian Trail, the Great Swamp, and the Maybrook Trailway. More than 10 routes are available for exploration.
Pawling features sections of the Appalachian Trail, including a 1,600-foot boardwalk over the Great Swamp and viewpoints like Cat Rocks. The Pawling Nature Reserve offers over 12 miles of trails with diverse natural communities. For more options, consult the Hiking around Pawling guide.
Yes, Pawling offers trails suitable for various skill levels, including easier options. The Appalachian Trail has sections with rolling paths, and the Pawling Nature Reserve provides well-maintained trails. For specific easy routes, refer to the Easy hikes around Pawling guide.
The Maybrook Trailway, a 15-mile (24 km) paved rail-trail, offers a scenic route for cyclists through woods and farm fields. This trail is part of the larger Empire State Trail. For detailed routes, explore the Road Cycling Routes around Pawling and Cycling around Pawling guides.
Lakeside Park provides wooded trails suitable for jogging, including a 1.68-mile (2.7 km) loop course. The Maybrook Trailway also offers a paved surface for running. More options can be found in the Running Trails around Pawling guide.
Key natural features include the Appalachian Trail, which passes through the region, and the expansive Great Swamp, accessible via a boardwalk. The Pawling Nature Reserve protects diverse ecosystems, and Cat Rocks offers views from approximately 1,100 feet (335 meters) above sea level.
Yes, approximately 16 miles (26 km) of the Appalachian Trail run through Pawling and Dover. This section is notably accessible, featuring the only Metro-North train station stop directly on the entire AT. Hikers can explore the Great Swamp boardwalk and climb Corbin Hill.
The Pawling Nature Reserve, managed by The Nature Conservancy, spans 1,060 acres (429 hectares) and features over 12 miles (19 km) of trails. It showcases diverse natural communities, including Duell Hollow Brook and views of the Great Swamp from Hammersley Ridge.
Pawling is a popular destination on komoot, with more than 600 visitors sharing their experiences. The routes in the region have an average rating of 4.58 out of 5 stars, indicating high satisfaction among users.
Komoot offers several guides for Pawling, including Hiking around Pawling, Easy hikes around Pawling, Road Cycling Routes around Pawling, Cycling around Pawling, and Running Trails around Pawling.
For general inquiries, the Village Clerk's office can be reached at (845) 855-1122 Ext. 10. Additional information and department-specific contacts are available on the official website. The official website for the Village of Pawling, NY is pawlingny.org.

