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.
Last updated: July 2, 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.
5.0
(1)
12
riders
23.6km
01:26
130m
130m
Easy bike ride. Great for any fitness level. 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.
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Popular around Southold
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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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