The best road cycling routes around Southold
4.8
(12)
556
riders
30
rides
Road cycling around Southold offers routes characterized by flat to gently rolling terrain, typical of coastal regions. The area features scenic roads that often run alongside the coastline, providing views of the water and access to charming villages. While significant elevation changes are uncommon, some routes include minor undulations. The landscape is primarily defined by its proximity to the water, agricultural fields, and occasional wooded sections.
Best road cycling routes around Southold
- The most popular road cycling route is Shelter…
Last updated: October 5, 2026
15
riders
164km
06:27
660m
660m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
30
riders
66.7km
02:50
180m
180m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
50.4km
02:03
150m
150m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
14
riders
13.5km
00:39
50m
50m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
13
riders
11.2km
00:26
30m
30m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Tips from the Community
A save beach, and one of a lot one Long Island
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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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Arshamomaque Cemetery, also known as the Hashamomack Old Families' Burying Ground, is open to the public and a great spot to stop by and check out some of the oldest graves on Long Island. Here lie settlers from the 17th, 18th, and 19th centuries, and the oldest known grave here is over 200 years old.
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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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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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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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The Shinnecock Canal was the first saltwater canal in New York State, built between 1884 and 1892. Once a site used by Native Americans to carry canoes over land, the Canal today connects two of the most stunning bays on Long Island's eastern side, Shinnecock Bay and Great Peconic Bay, which had become landlocked over time. Though the Hamptons officially begin 10 miles (16.09 km) west of the Canal, it is known as the starting point of this exclusive summer resort, as every modern bridge leading to the Hamptons crosses the Canal.
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Frequently Asked Questions
How many road cycling routes are available in Southold?
Southold offers over 20 road cycling routes, catering to various skill levels. You'll find a good selection of easy, moderate, and even some challenging options to explore the region's coastal landscapes and charming villages.
What kind of terrain can I expect on road cycling routes in Southold?
Road cycling in Southold is characterized by flat to gently rolling terrain, typical of coastal regions. Routes often run alongside the coastline, providing scenic views of the water, agricultural fields, and occasional wooded sections. Significant elevation changes are uncommon, making it accessible for many riders.
Are there easy road cycling routes suitable for beginners in Southold?
Yes, Southold has a great selection of easy road cycling routes. For instance, the Truman's Beach – Orient Beach loop from Village of Greenport is an easy 21.6-mile path offering coastal views and passing through local points of interest. Another accessible option is the Shelter Island Heights loop from Town of Shelter Island, which is 23.0 km long.
Where can I find longer or more advanced road cycling routes in Southold?
For those seeking a longer or more challenging ride, the Foster Memorial Bathing Beach – Sag Harbor loop from Greenport is a difficult 164.0 km trail. A moderate option that offers varied scenery across Shelter Island is the Shelter Island Heights loop from Silver Beach, which is 45.7 km.
What are some scenic road cycling routes in Southold?
Many routes in Southold offer scenic coastal views. The Truman's Beach – Orient Beach loop from Village of Greenport provides beautiful coastal vistas. Another popular choice for its coastal landscapes is the Mitchell Park – Orient Beach loop from Peconic, which also passes through charming areas.
Are there any loop road cycling trails in Southold?
Yes, many of the road cycling routes in Southold are designed as loops, allowing you to start and end in the same location. Popular loop options include the Shelter Island Heights loop from Silver Beach and the Mitchell Park – Orient Beach loop from Peconic.
What can I see along the road cycling routes in Southold?
Along Southold's road cycling routes, you can discover various points of interest. Consider visiting Shelter Island Heights, the historic village of Sag Harbor, or enjoying the views from Mitchell Park. You might also pass by natural areas like Elizabeth A. Morton National Wildlife Refuge or Inlet Pond County Park.
What do other road cyclists enjoy most about road cycling in Southold?
The road cycling routes in Southold are highly rated by the komoot community, with an average score of 4.8 stars from over 10 reviews. Cyclists often praise the scenic coastal roads, the flat terrain, and the beautiful views of the Long Island Sound and Peconic Bay.
Are there any routes that avoid heavy car traffic in Southold?
While many routes utilize public roads, Southold's coastal and agricultural areas often feature quieter roads, especially outside of peak tourist season. Routes that explore Shelter Island, such as the Shelter Island Heights loop from Town of Shelter Island, can offer a more serene cycling experience due to the island's generally lower traffic volume.
What is the typical duration for road cycling routes in Southold?
The duration of road cycling routes in Southold varies depending on the distance and your pace. Easy routes like the Truman's Beach – Orient Beach loop (34.7 km) can take around 1 hour 30 minutes. Moderate routes, such as the Shelter Island Heights loop from Silver Beach (45.7 km), typically take about 2 hours. Longer, more challenging routes will naturally require more time.
Are there any road cycling routes that pass by beaches in Southold?
Yes, several road cycling routes in Southold offer access to or views of beaches. The Truman's Beach – Orient Beach loop from Village of Greenport specifically passes by Orient Beach. You might also encounter Hashamomuck Beach on some coastal rides.
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