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Cycling routes
United States
New York
Suffolk County

Southold

The best cycling routes around Southold

4.6

(10)

189

riders

14

rides

Touring cycling around Southold, located on the North Fork of Long Island, New York, offers diverse landscapes for exploration. The region features a blend of coastal areas, tranquil roads, and natural preserves, providing varied terrain for cyclists. Routes often include views of the Long Island Sound and Southold Bay, with some paths leading through forest and wetland habitats. The area's relatively flat topography makes it suitable for a range of cycling abilities.

Best touring cycling routes around Southold

  • The most popular touring cycling route is Hashamomuck Beach – Orient Beach State Park loop from Southold, a 29.8 miles (47.9 km) trail that takes 2 hours 42 minutes to complete. This moderate route offers scenic coastal views and passes through Orient Beach State Park.
  • Another top favourite among local touring cyclists is Shelter Island Heights – Dickerson Creek loop from Shelter Island, a moderate 26.4 miles (42.5 km) path. This route explores Shelter Island, including views of the Shelter Island Heights Historic District.
  • Local touring cyclists also love the Shelter Island Heights loop from Village of Dering Harbor, a 14.7 miles (23.6 km) trail leading through Shelter Island's coastal areas, often completed in about 1 hour 26 minutes.
  • Touring cycling around Southold is defined by coastal views, tranquil roads, and diverse natural preserves. The network offers options for easy rides to more moderate routes, catering to different fitness levels.
  • The routes in Southold are highly rated by the komoot community with an average score of 4.6 stars from over 13 reviews. More than 199 touring cyclists have used komoot to explore Southold's varied terrain.

Last updated: July 29, 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

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 Southold

Hiking around Southold

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Road Cycling Routes around Southold

Tips from the Community

Gary
June 8, 2025, Beach

Beware of broken shells

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

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Nice views of the creek and out to the bay.

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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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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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Frequently Asked Questions

How many touring cycling routes are available in Southold?

Southold offers a good selection of touring cycling routes, with over 15 routes documented on komoot. These routes cater to various preferences, including 8 easy and 7 moderate options, ensuring there's something for every cyclist.

What is the overall difficulty level of touring cycling routes in Southold?

The touring cycling routes in Southold are generally accessible, with a mix of easy and moderate options. You'll find 8 easy routes perfect for a relaxed ride, and 7 moderate routes for those looking for a bit more challenge. There are no difficult routes listed, making the area suitable for a wide range of cyclists.

Are there any circular touring cycling routes in Southold?

Yes, many of the touring cycling routes in Southold are designed as loops, offering convenient circular journeys. For example, the Shelter Island Heights – Dickerson Creek loop from Shelter Island is a popular moderate option, and the Shelter Island Heights loop from Village of Dering Harbor provides an easier circular ride.

What kind of landscapes can I expect to see while touring cycling in Southold?

Touring cycling in Southold offers a diverse range of landscapes. You can expect scenic coastal views along the Long Island Sound and Southold Bay, tranquil roads winding through natural preserves, and paths that take you through forest and wetland habitats. The area's relatively flat topography allows for enjoyable rides through these varied environments.

What natural features can I explore along touring cycling routes in Southold?

Southold is rich in natural beauty. Many routes will take you past stunning coastal areas like Hashamomuck Beach and Orient Beach State Park. You can also explore preserves and ponds such as Arshamomaque Pond, Dam Pond, and Laurel Lake Preserve. For specific natural highlights, consider visiting Mashomack Preserve or Elizabeth A. Morton National Wildlife Refuge.

Are there any historical landmarks or points of interest accessible by bike in Southold?

Absolutely. Southold offers several historical landmarks and points of interest that are great to visit by bike. The Shelter Island Heights Historic District, known for its preserved Victorian houses, is a highlight on routes like the Shelter Island Heights – Dickerson Creek loop from Shelter Island. You can also visit the historic Horton Point Lighthouse, offering scenic views of the Long Island Sound. For more local attractions, you can explore the Attractions around Southold guide.

Are there family-friendly touring cycling routes in Southold?

Yes, Southold has several family-friendly touring cycling routes, particularly the easier ones. The relatively flat terrain and scenic views make it enjoyable for all ages. Routes like the Shelter Island Heights loop from Village of Dering Harbor, which is an easy 23.6 km ride, are great options for families.

Where can I find parking for touring cycling routes in Southold?

Parking availability varies by route and starting point. Many state parks and public access points in Southold, such as Orient Beach State Park, offer designated parking areas. When planning your ride, it's advisable to check specific route details for parking information near your chosen starting location. For general information on places of interest, you can consult the Southold Town website's Places of Interest section.

Is public transport available to reach touring cycling routes in Southold?

Public transport options to reach touring cycling routes in Southold are available, though they might require some planning. The Long Island Rail Road (LIRR) provides service to the North Fork, including stations in Southold and Greenport, which can be a starting point for many routes. Additionally, accessing Shelter Island often involves a short ferry ride, which accommodates cyclists.

What do other touring cyclists enjoy the most about touring cycling in Southold?

The touring cycling experience in Southold is highly regarded by the komoot community, with an average rating of 4.6 stars from over 13 reviews. Cyclists frequently praise the region's diverse landscapes, including coastal views and tranquil roads, as well as the well-maintained paths that make for enjoyable rides. The blend of natural beauty and charming local attractions also contributes to a positive experience.

Are there any wineries along or near touring cycling routes in Southold?

Yes, the North Fork of Long Island, including Southold, is renowned for its vineyards. Many touring cycling routes pass through or near beautiful wineries such as Mattebella Vineyards and The Old Field Vineyards. These offer a chance to integrate a tasting experience into your ride, enjoying the scenic surroundings and local produce.

What is the best time of year for touring cycling in Southold?

The best time for touring cycling in Southold is generally from spring through fall. The weather during these seasons is typically pleasant, offering comfortable temperatures for riding. Summer provides warm conditions perfect for coastal rides, while spring and fall offer cooler temperatures and beautiful foliage, especially in the more wooded areas.

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