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United States
New York
Suffolk County

Shelter Island Heights

The best cycling routes around Shelter Island Heights

4.6

(12)

187

riders

26

rides

Best touring cycling routes Shelter Island Heights offer a diverse landscape for exploration. The island features a mix of green hills, sandy beaches, and dense woods, with nearly one-third dedicated to preserves like Mashomack Nature Preserve. Cycling routes often follow well-paved roads, though some sections may include sandy gravel. The region's 20 miles of coastline provide varied views of Peconic Bay and Gardiners Bay.

Best touring cycling routes around Shelter Island Heights

  • The most popular touring cycling route is Shelter Island Heights – Dickerson Creek loop from Shelter Island, a 26.4 miles (42.5 km) trail that takes 2 hours 36 minutes to complete, offering varied terrain through the island's interior.
  • Another top favourite among local touring cyclists is Shelter Island Heights loop from Shelter Island Heights, a moderate 22.2 miles (35.7 km) path. This route provides views of coastal areas and passes through wooded sections.
  • Local touring cyclists also love the Hashamomuck Beach – Orient Beach State Park loop from Southold, a 29.8 miles (47.9 km) trail leading through coastal landscapes and natural preserves, often completed in about 2 hours 43 minutes.
  • Touring cycling around Shelter Island Heights is defined by green hills, coastal paths, and dense woodlands. The network offers options for different ability levels, from easy loops to more challenging distances.
  • The routes in Shelter Island Heights are highly rated by the komoot community with an average score of 4.6 stars from over 10 reviews. More than 200 touring cyclists have used komoot to explore Shelter Island Heights's varied terrain.

Last updated: October 5, 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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5.0

(1)

12

riders

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

4.5

(2)

17

riders

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

Moderate

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
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Popular around Shelter Island Heights

Hiking around Shelter Island Heights

Running Trails around Shelter Island Heights

Road Cycling Routes around Shelter Island Heights

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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Custer Institute and Observatory, established in 1927, opens exclusively on Saturdays from 7 p.m. to 12 a.m. for Saturday Night Observing. Long Island's oldest public observatory offers tours led by knowledgeable volunteer staff members. Visitors can tour the facilities and view the night sky through powerful telescopes, as well as explore the library, exhibit room, and gift shop. Custer Institute and Observatory also hosts lectures, classes, concerts, art exhibits, and other special events.

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Alex
February 21, 2024, Hummels Pond

You gain a good view of this lake as you cycle past it. Set in peaceful surroundings, it is worth taking a look for the varied wildlife that inhabit it as you cycle by.

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Alex
February 6, 2024, Lake view

You gain a good view of this lake as you cycle past it. Set in peaceful surroundings, it is worth taking a look for the varied wildlife that inhabit it as you cycle by.

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Alex
February 6, 2024, Horton Point Lighthouse

Horton Point Lighthouse, situated on the northeastern coast of Long Island, has guided sailors since 1857. Its iconic beacon served as a vital maritime aid, guiding ships through treacherous waters. Today, it stands as a cherished historic landmark, preserving the rich seafaring heritage of the region for future generations.

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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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Frequently Asked Questions

How many touring cycling routes are available in Shelter Island Heights?

There are over 25 touring cycling routes available in Shelter Island Heights, catering to various skill levels. This includes 14 easy routes, 13 moderate routes, and 1 difficult route, ensuring options for every cyclist.

What kind of terrain can I expect on touring cycling routes in Shelter Island Heights?

Cyclists can expect a diverse landscape, including green hills, majestic beaches, and dense woods. Most routes follow well-paved roads, but some sections, like the spur to Shell Beach, may feature sandy gravel. The island's extensive preserves, such as Mashomack Nature Preserve, offer varied natural beauty.

Are there any family-friendly touring cycling routes in Shelter Island Heights?

Yes, Shelter Island Heights offers several easy touring cycling routes suitable for families. For example, the Shelter Island Heights loop from Village of Dering Harbor is an easy 23.6 km (14.7 miles) route that takes approximately 1 hour 26 minutes, providing a pleasant experience for all ages.

What are some scenic viewpoints or attractions I can visit along the cycling routes?

Many routes offer breathtaking views of Peconic Bay and Gardiners Bay. You can also explore historic architecture in areas like "The Heights" with its gingerbread cottages, or visit landmarks such as Shelter Island Heights itself. The Mashomack Preserve is another significant natural attraction along some routes.

Are there any circular touring cycling routes on Shelter Island Heights?

Yes, many touring cycling routes in Shelter Island Heights are circular, allowing you to start and end at the same point. A popular moderate option is the Shelter Island Heights loop from Shelter Island Heights, which covers 35.7 km (22.2 miles) and offers coastal and wooded sections.

What do other touring cyclists say about the routes in Shelter Island Heights?

The touring cycling routes in Shelter Island Heights are highly rated by the komoot community, with an average score of 4.6 out of 5 stars from over 10 reviews. Cyclists often praise the diverse terrain, from green hills to coastal paths, and the well-maintained roads that make for an enjoyable ride.

Can I reach Shelter Island Heights by public transport with my bike?

Shelter Island is primarily accessed by ferry. You can take a ferry to the island with your bicycle, which is a popular way to start a touring cycling adventure. It's advisable to check the ferry schedules in advance.

Where can I find parking for touring cycling routes in Shelter Island Heights?

Parking is generally available at various points around Shelter Island Heights, especially near ferry terminals or public access areas. Many cyclists opt to take the ferry to the island and begin their tour directly from there, eliminating the need for car parking on the island itself.

Are there any natural preserves or wildlife areas accessible by bike?

Absolutely. A significant portion of Shelter Island is preserved land. The Mashomack Nature Preserve, covering 2,000 acres, is a prime example, offering rich habitats and natural beauty. Other preserves like Mildred Flower Hird Nature Preserve and Crab Creek Preserve also contribute to the island's abundant natural areas, where you might spot blue herons or ospreys.

What is a good moderate touring cycling route for exploring the island's interior?

For a moderate route exploring the island's interior, consider the Shelter Island Heights – Dickerson Creek loop from Shelter Island. This 42.5 km (26.4 miles) route takes approximately 2 hours 36 minutes and offers varied terrain through the heart of the island.

Are there any coastal touring cycling routes that include beaches or state parks?

Yes, you can find routes that lead through coastal landscapes and natural preserves. The Hashamomuck Beach – Orient Beach State Park loop from Southold is a moderate 47.9 km (29.8 miles) trail that takes about 2 hours 43 minutes, offering views of coastal areas and leading to a state park.

Where can I find maps of Shelter Island's open spaces and cycling routes?

Maps of Shelter Island's walkable open space and preserved land, which can be helpful for cyclists, are often available locally. You can also check resources like the official town website for more information: shelterislandtown.gov/266/Maps-Trails.

Most popular routes around Shelter Island Heights

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