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United States
New York
Suffolk County

Dering Harbor

The best cycling routes around Dering Harbor

4.8

(6)

148

riders

12

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.

Best touring cycling routes around Dering Harbor

  • The most popular touring cycling route is Shelter Island Heights – Dickerson Creek loop from Shelter Island, a…

Last updated: August 8, 2026

5.0

(1)

39

riders

#1.

Shelter Island Heights – Dickerson Creek loop from Shelter Island

55.4km

03:26

330m

330m

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

4.5

(2)

17

riders

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Popular around Dering Harbor

Hiking around Dering Harbor

Running Trails around Dering Harbor

Road Cycling Routes around Dering Harbor

Tips from the Community

gabinchuck
May 27, 2025, Orient Beach State Park

Nice State Park with a swim beach, hiking trails, picnic area, snack bar, great birding, etc.

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Andrus
February 23, 2024, Truman's Beach

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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Alex
February 21, 2024, Hashamomuck Beach

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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Jamie S.
January 23, 2024, Little Bay

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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Oyster Ponds Waterway Access Site is home to Truman's Beach. It's a good kayak launch site and fishing spot. You can ride by and enjoy seeing the clear blue water, and you can even stop for a dip. Visit in the evening to catch a great sunset.

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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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Scott
January 10, 2024, Shelter Island Heights

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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Frequently Asked Questions

How many touring cycling routes are available around Dering Harbor?

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.

Are there any easy touring cycling routes suitable for beginners or families?

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.

What kind of terrain can I expect on touring cycling routes in Dering Harbor?

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.

Are there any circular touring cycling routes around Dering Harbor?

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.

What are some scenic viewpoints or natural features to look out for on the routes?

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.

What attractions or points of interest can I explore along the touring cycling routes?

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.

Are there any places to stop for refreshments or food during a touring cycling trip?

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.

What do other touring cyclists enjoy most about cycling in Dering Harbor?

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.

Can I combine touring cycling with other outdoor activities in the area?

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.

Are there any routes that offer views of lakes or ponds?

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.

What is the longest touring cycling route available?

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.

Is it possible to start a touring cycling route directly from the Village of Dering Harbor?

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.

Most popular routes around Dering Harbor

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