5.0
(3)
51
hikers
7
hikes
Hiking around Dering Harbor offers access to the tranquil coastal landscapes and natural beauty of Shelter Island. The region is characterized by its picturesque harbor, waterfront views, and proximity to preserves with varied terrain. While Dering Harbor itself is small, its location provides opportunities for peaceful walks and exploring the island's natural splendor. The area features gentle elevations and a serene ambiance, ideal for outdoor pursuits.
Last updated: June 24, 2026
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.

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1
hikers
1.83km
00:28
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.
5.0
(3)
16
hikers
13.1km
03:21
50m
50m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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Popular around Dering Harbor
Nicoll's Creen is a marshy bay, part of Mashomack Preserve. This area is great for birdwatching and a scenic spot for a break.
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Be enchanted by the vibrant flutter of butterflies in the dedicated butterfly garden. This colorful haven is a delight for families and nature enthusiasts alike.
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Nestled on Shelter Island, Mashomack Preserve is a 2,039-acre natural wonderland. It features diverse ecosystems from woodlands to tidal creeks, offering picturesque trails for hikers. Rich in biodiversity, it's a haven for birdwatchers and nature enthusiasts, showcasing the beauty of Long Island's wildlife.
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The trails around Dering Harbor, particularly on Shelter Island, are generally characterized by gentle coastal landscapes and serene natural environments. You'll find paths suitable for tranquil strolls rather than rugged climbs. For instance, the Arshamomaque Preserve Red Trail offers very minimal elevation gain, making it ideal for an easy walk.
Yes, Dering Harbor and the surrounding Shelter Island area offer several easy and short options. The Mashomack Red Trail is an easy 2.8 km route with minimal elevation, perfect for a relaxed walk. Another great choice is the Inlet Pond County Park Black Trail and Blue Trail, which is just under 2 km and also rated easy.
The region is rich in natural beauty and historical points of interest. You can explore the diverse ecosystems of Mashomack Preserve, known for its forests and coastal views. Inlet Pond County Park offers serene lake views, while Hashamomuck Beach is perfect for enjoying sandy shores and sunsets. Further afield, the historic Cedar Point & Cedar Island Lighthouse stands as a maritime icon.
Yes, there are several excellent circular routes available. For a longer, moderate option, consider the Mashomack Preserve loop, which covers about 13 km. Another moderate loop is the Mashomack Red, Yellow, Green and Jone C. Coles Loop, spanning nearly 9 km.
The warmer months are generally ideal for hiking around Dering Harbor and Shelter Island. This period brings vibrant greenery and clear waters, creating an inviting climate for outdoor pursuits. The tranquil ambiance of the area is best enjoyed when the weather is mild, allowing for comfortable walks along the waterfront and through preserves.
Absolutely. The region's emphasis on peaceful walks and gentle terrain makes it very suitable for families. Many trails are short and easy, such as those found in Inlet Pond County Park or the Arshamomaque Preserve Red Trail, which are perfect for younger hikers or those looking for a leisurely outing.
The area is highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the serene coastal environment, the peaceful atmosphere, and the opportunity for tranquil walks that allow for appreciation of Shelter Island's natural beauty.
While Dering Harbor itself is a village, access to many of the natural preserves and parks on Shelter Island, such as Mashomack Preserve, may have specific entry requirements or suggested donations. It's always advisable to check the official websites of individual preserves or parks for the most current information regarding permits or fees before your visit.
Dering Harbor and the wider Shelter Island area offer various options for dining and accommodation. The village itself is known for its exclusive ambiance, and you'll find establishments catering to visitors. For more options, explore nearby areas on Shelter Island, which provide a range of cafes, pubs, and places to stay after your hike.
Hiking trails around Dering Harbor and Shelter Island generally feature very modest elevation gains, making them accessible for most fitness levels. For example, the Mashomack Red Trail has an elevation gain of only about 14 meters, while even longer routes like the Mashomack Preserve loop only climb around 52 meters over its 13 km distance.


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