Ossining is a region in Westchester County, New York, defined by its diverse landscape and proximity to the Hudson River. Its terrain features rolling hills and dense woodlands, offering varied environments for outdoor activities. This area provides opportunities for several sports like hiking, touring cycling, jogging, road cycling, and more. The natural setting makes it suitable for exploring a range of routes.
Ossining offers a variety of outdoor activities across 8 routes, catering to several…
75
Routes
4.7
(46)
Average rating
1126
People visited

2
hikers
2.72km
00:46
50m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

3.09km
00:48
20m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

2.21km
00:38
60m
60m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

1.60km
00:25
10m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?

4.0
(4)
72
riders
11.3km
01:05
190m
190m
Moderate mountain bike ride. Great for any fitness level. Advanced riding skills necessary.

5.0
(5)
63
riders
8.31km
00:49
160m
160m
Moderate mountain bike ride. Great for any fitness level. Advanced riding skills necessary.

3.0
(2)
16
riders
6.50km
00:39
130m
120m
Hard mountain bike ride. Great for any fitness level. Advanced riding skills necessary. Some portions of the route may require you to push your bike.

8
riders
32.0km
02:32
440m
440m
Moderate mountain bike ride. Good fitness required. Advanced riding skills necessary.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?

6
riders
59.2km
03:08
690m
690m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

21
riders
61.4km
02:38
500m
500m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

18
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

7
riders
26.9km
01:20
330m
330m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?

5
riders
36.3km
02:28
450m
450m
Hard bike ride. Good fitness required. You may need to push your bike for some segments of this route.

1
riders
34.9km
02:34
360m
360m
Hard bike ride. Good fitness required. You may need to push your bike for some segments of this route.

1
riders
55.8km
03:36
680m
680m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(2)
37
riders
27.9km
01:36
120m
120m
Easy bike ride. Great for any fitness level. 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?

95
runners
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

77
runners
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

75
runners
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

20
runners
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?

3.9
(10)
16
riders
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4.5
(2)
8
riders
47.1km
03:19
390m
390m
Hard gravel ride. Good fitness required. You may need to push your bike for some segments of this route.

5.0
(1)
8
riders
26.5km
01:31
190m
190m
Hard gravel ride. Good fitness required. You may need to push your bike for some segments of this route.

5.0
(1)
2
riders
43.5km
02:35
290m
290m
Moderate gravel ride. 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?
Ossining offers a variety of outdoor activities, including Hiking, Touring cycling, Jogging, Road cycling, Mountain biking, and Gravel biking. The region features 8 routes, which have received an average rating of 4.73 stars from more than 5,000 visitors on komoot.
Ossining provides numerous hiking opportunities, including trails at Teatown Lake Reservation and sections of the historic Old Croton Aqueduct. These areas offer diverse landscapes for exploration. For more details, refer to the Hiking around Ossining guide.
Yes, Ossining features easy hiking routes suitable for various skill levels. The Old Croton Aqueduct offers relatively flat sections, and Teatown Lake Reservation has trails of varying difficulty. Explore options in the Easy hikes around Ossining guide.
Ossining is suitable for touring cycling, road cycling, mountain biking, and gravel biking. Notable routes include the New Croton Reservoir Loop and sections of the Old Croton Aqueduct. The Cycling around Ossining guide provides further information.
Joggers can utilize paved paths like the Sing Sing Kill Greenway and sections of the North County Trailway. Many local parks also offer suitable terrain for running. For specific routes, consult the Running Trails around Ossining guide.
Ossining offers opportunities for mountain biking, with trails available in the region's diverse landscape. These routes cater to different experience levels. More information can be found in the MTB Trails around Ossining guide.
Key scenic highlights include views of the Hudson River from waterfront parks like Louis Engel, the New Croton Reservoir, and the historic Old Croton Aqueduct with its famous 'double arch.' Teatown Lake Reservation also offers natural beauty.
Ossining provides several family-friendly options, such as walking along the paved Sing Sing Kill Greenway or exploring easier trails at Teatown Lake Reservation. Many local parks also offer recreational spaces suitable for families.
Outdoor activities in Ossining are popular on komoot, with more than 5,000 visitors having explored the region. The 8 available routes have received 233 ratings, averaging 4.73 out of 5 stars.
Komoot offers several guides for Ossining, including Easy hikes around Ossining, Hiking around Ossining, Cycling around Ossining, and Running Trails around Ossining. Guides for road cycling, mountain biking, and gravel biking are also available.
Official information about the Village of Ossining can be found on their website at www.villageofossining.org. For direct inquiries, the Village of Ossining can be reached by phone at +19149413554.

