4.7
(7)
147
riders
11
rides
Touring cycling around Dering Harbor offers routes through picturesque coastal landscapes and verdant scenery on Shelter Island. The area features bay views and access to numerous beaches, providing a mix of paved and some hard-packed gravel sections. Routes are generally designed to avoid steep climbs, making for an enjoyable cycling experience across varied terrain.
Last updated: May 16, 2026
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.
5.0
(1)
16
riders
32.0km
01:58
170m
170m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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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.
4.5
(2)
16
riders
22.2km
01:20
160m
160m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
riders
15.7km
00:55
90m
90m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Dering Harbor
Nice State Park with a swim beach, hiking trails, picnic area, snack bar, great birding, etc.
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Nice little beach out towards the end of the North Fork of Long Island. The "sand" is actually more rock so bare feet might get a bit sore. The sunsets can be incredible on the right day.
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Hashamomuck Beach, composed of sand and shells, sits just off Highway 48. It provides a picturesque spot for enjoying sunsets or sunrises. Visitors can enjoy the sound of small, crashing waves and make use of the ample parking.
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Orient Beach is a small, beautiful beach on a narrow strip of land on Orient Point. The beach is part of Orient Beach State Park and a must visit if in the area.
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Little Bay is a narrow bay on the southeastern side of Orient Point. With Little Bay on one side of the road, and Gardner's Bay on the other, you are surrounded by water on this unique stretch of road.
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Ram Island County Park is a beautiful little headland park and it makes for a good bike ride. Whilst you will not be able to have coastal views all the way, the ones you will have will be super good and the rest will be along tranquil tree lined roads. It's nice too as once you are down on the headland, you can do a small loop to come back a slightly different way.
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Explore the Shelter Island Heights Historic District, lined with preserved Victorian houses and offering a glimpse into the island's past.
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This picturesque peninsula known for its vibrant shells and serene atmosphere, is a great place to search for treasures like seashells, colorful stones, and maybe even a piece of sea glass.
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There are 13 touring cycling routes available around Dering Harbor. These routes offer a mix of easy and moderate options, with 7 easy routes and 6 moderate routes, ensuring there's something for various skill levels.
Yes, Dering Harbor offers several easy touring cycling routes perfect for beginners or families. One excellent option is the Shelter Island Heights loop from Village of Dering Harbor, which is 23.6 km long and generally takes about 1 hour 26 minutes to complete. This route allows you to enjoy the scenic beauty without challenging climbs.
The touring cycling routes around Dering Harbor primarily feature paved roads, offering a smooth ride. Some routes may include short sections of hard-packed gravel, such as the spur to Shell Beach, which is generally manageable even for road bikes. The area is known for avoiding steep climbs, making for a more relaxed cycling experience through picturesque coastal and verdant landscapes.
Yes, many of the touring cycling routes around Dering Harbor are circular, allowing you to start and end at the same point. A popular moderate loop is the Shelter Island Heights loop from Shelter Island Heights, which covers 35.7 km and provides a comprehensive tour of the island's charming villages and natural features.
Dering Harbor and Shelter Island are rich in scenic beauty. You'll encounter picturesque harbors, breathtaking views of the Peconic Bay, beautiful green hills, and majestic beaches. Routes often pass by numerous beaches, and you can enjoy verdant landscapes throughout your ride. The Dering Harbor Inn, for example, offers spectacular views over the harbor.
There are several interesting places to explore. You can cycle through the charming Shelter Island Heights, visit Hashamomuck Beach, or explore Orient Beach State Park. For those interested in history or science, the Custer Institute and Observatory and Cedar Point & Cedar Island Lighthouse are also nearby.
Absolutely! The area offers several pleasant stops. The Farmstand at Sylvester Manor is a popular choice for fresh vegetables, baked goods, and cold drinks. You might also enjoy a stop at the Shelter Island Craft Brewery, which has outdoor tables and tastings. For a post-ride treat, the Dering Harbor Inn features a gelato stand.
The touring cycling routes in Dering Harbor are highly rated by the komoot community, with an average score of 4.7 stars from over 9 reviews. Cyclists often praise the picturesque coastal landscapes, the verdant scenery, and the generally flat terrain that makes for an enjoyable and relaxed ride. The variety of routes, from easy to moderate, is also frequently appreciated.
Yes, Dering Harbor and Shelter Island are excellent for combining cycling with other outdoor pursuits. For instance, you can park your bike and enjoy an optional nature hike at Mashomack Preserve. The region also offers opportunities for running, swimming, and general hiking, making it a versatile destination for outdoor enthusiasts.
While Dering Harbor is known for its bay and coastal views, you can also find routes that pass by serene water bodies. For example, you might encounter areas near Inlet Pond County Park or Nicoll's Creen, offering a different natural landscape to enjoy during your ride.
The longest touring cycling route around Dering Harbor is the Hashamomuck Beach – Orient Beach State Park loop from Southold. This route spans 47.9 km and typically takes about 2 hours 43 minutes to complete, leading you through coastal areas and parkland.
Yes, you can certainly start your touring cycling adventure directly from the Village of Dering Harbor. The Shelter Island Heights loop from Village of Dering Harbor is an easy 23.6 km route that begins and ends in the village, allowing you to explore the area's charm right from the start.


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