Dering Harbor is a village located on Shelter Island, New York, offering access to the island's diverse natural environment. The region features preserved wetlands, woodlands, and scenic coastlines, providing varied terrain for outdoor activities. Approximately one-third of Shelter Island is maintained in its natural state, making it suitable for several sports like hiking, touring cycling, road cycling, and jogging.
Outdoor enthusiasts exploring Dering Harbor will find 2 routes available for various activities. More than…
28
Routes
4.6
(11)
Average rating
388
People visited

19
hikers
8.91km
02:18
50m
50m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

10
hikers
2.81km
00:44
10m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

1.26km
00:19
0m
0m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

1.83km
00:28
10m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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5
runners
13.1km
01:36
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

13
runners
9.96km
01:02
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

13
runners
12.5km
01:19
90m
90m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

9
runners
5.73km
00:36
20m
20m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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4.8
(4)
82
riders
47.5km
02:17
360m
360m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

5.0
(1)
43
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

15
riders
164km
06:27
660m
660m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

12
riders
11.2km
00:26
30m
30m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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5.0
(1)
39
riders
55.4km
03:26
330m
330m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4.0
(1)
21
riders
47.9km
02:43
120m
120m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4
riders
19.4km
01:08
60m
60m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

7
riders
22.4km
01:20
140m
140m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Dering Harbor, located on Shelter Island, offers a range of outdoor activities including hiking, touring cycling, road cycling, and jogging. The region features preserved wetlands, woodlands, and scenic coastlines suitable for these pursuits. Approximately one-third of Shelter Island is maintained in its natural state.
Mashomack Preserve is a prominent hiking destination near Dering Harbor, offering over 20 miles (32 km) of trails through diverse habitats. Sylvester Manor Educational Farm also provides nearly 5 miles (8 km) of footpaths through old-growth forests and along Gardiners Creek. For more options, consult the Hiking around Dering Harbor guide.
Yes, there are easy hiking options available in the Dering Harbor area. Mashomack Preserve offers trails suitable for various skill levels, including less strenuous paths. The Easy hikes around Dering Harbor guide highlights specific routes designed for accessibility.
Dering Harbor and Shelter Island offer routes for both touring and road cycling. These routes traverse picturesque coastal landscapes, providing bay views and access to beaches. The Cycling around Dering Harbor guide details various options for cyclists.
The diverse landscape of Shelter Island, with its preserved wetlands, woodlands, and coastlines, offers varied scenery for jogging. A network of trails winds through diverse ecosystems, providing a tranquil environment for runners. Specific routes can be found in the Running Trails around Dering Harbor guide.
Mashomack Preserve is a significant natural area on Shelter Island, encompassing 2,350 acres of interlacing tidal creeks, oak woodlands, fields, and freshwater marshes. It features 11 miles (18 km) of coastline and over 20 miles (32 km) of hiking trails. The preserve is considered a rich habitat in the Northeast.
Sylvester Manor Educational Farm is a historic site near Dering Harbor offering nearly 5 miles (8 km) of roadways, groomed trails, and footpaths. Visitors can explore old-growth forests, open fields, and the shorefront of Gardiners Creek. The site connects to the maritime history of Shelter Island.
Yes, Dering Harbor and the surrounding Shelter Island offer family-friendly outdoor activities. The generally flat terrain and diverse trails in areas like Mashomack Preserve and Sylvester Manor are suitable for various ages. Easy hiking and cycling routes provide accessible options for families.
Dering Harbor is a popular destination for outdoor enthusiasts on komoot. More than 600 visitors have shared their experiences, with routes receiving an average rating of 4.82 out of 5 stars. There are 2 routes currently available for various activities.
Komoot offers several guides for Dering Harbor, including Hiking around Dering Harbor, Easy hikes around Dering Harbor, and Cycling around Dering Harbor. Guides for road cycling and running are also available.
The official website for the Incorporated Village of Dering Harbor is deringharborvillage.org. For direct inquiries, the Village of Dering Harbor can be reached by phone at +1-631-749-0020.
Cycling routes around Dering Harbor and Shelter Island generally feature picturesque coastal landscapes and verdant scenery. Routes are designed to avoid steep climbs, offering an enjoyable experience across varied terrain. This includes both paved roads and some hard-packed gravel sections.
Yes, specific routes are available for road cycling around Dering Harbor. These routes often provide comprehensive tours of Shelter Island's charming villages and natural features. The Road Cycling Routes around Dering Harbor guide offers detailed information.

