4.7
(9)
298
riders
15
rides
Road cycling around Village of Greenport offers routes through diverse landscapes, characterized by generally flat terrain and low-traffic country roads. The area features picturesque paths winding through lush farmland, vineyards, and small towns, often skirting the coast. Cyclists can expect mostly well-paved surfaces, with many routes presenting no significant hills. The region's natural features include salt marshes, red cedar forests, and expansive coastal views.
Last updated: August 26, 2026
4.7
(3)
90
riders
53.9km
02:33
380m
380m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(1)
44
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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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.
11
riders
37.8km
01:36
120m
120m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Village of Greenport
Nice State Park with a swim beach, hiking trails, picnic area, snack bar, great birding, etc.
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A save beach, and one of a lot one Long Island
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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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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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There are over 15 road cycling routes around Village of Greenport listed on komoot, offering diverse options for cyclists. These routes are highly rated by the komoot community, with an average score of 4.8 stars from over 9 reviews.
Yes, Village of Greenport offers many easy road cycling routes. Out of the 15 available, 12 are classified as easy, making them ideal for beginners or family outings. An example is the Truman's Beach – Orient Beach loop from Village of Greenport, an easy 21.6-mile path with coastal views.
Road cycling in Village of Greenport is characterized by generally flat terrain and low-traffic country roads. You'll find picturesque paths winding through lush farmland, vineyards, and small towns, often skirting the coast. Most routes feature well-paved surfaces with no significant hills, though longer routes may include modest climbs.
For experienced riders seeking a challenge, there is at least one difficult route available. The Foster Memorial Bathing Beach – Sag Harbor loop from Greenport is a demanding 102-mile route with significant elevation gain, offering a substantial ride for those with good fitness.
Many routes offer expansive coastal views and pass through picturesque farmland. You can also explore specific attractions like Orient Beach State Park, known for its unique salt marshes and red cedar forests. Mitchell Park also offers great views. For a cultural stop, consider the Custer Institute and Observatory.
Yes, many of the road cycling routes around Village of Greenport are circular. For instance, the popular Shelter Island Heights loop from Silver Beach is a 28.4-mile circular route, and the Shelter Island Heights loop from Town of Shelter Island is a shorter 14.3-mile option.
The region is enjoyable for road biking across multiple seasons. Spring and fall offer pleasant temperatures and beautiful scenery, with fewer crowds. Summer is also popular, though it can be warmer. Winter riding is possible, but cyclists should be prepared for colder conditions and potentially less daylight.
While specific parking details for each route vary, many routes start from or pass through areas with public parking. For example, routes around Orient Beach State Park would likely have parking within the park. When planning your ride on komoot, check the route details for suggested starting points and parking information.
The area is highly rated by the komoot community, with an average score of 4.8 stars. Reviewers often praise the low-traffic country roads, the scenic views of vineyards and the coast, and the generally flat, well-paved surfaces that make for an enjoyable ride. The diversity of routes, from easy coastal loops to more challenging distances, is also frequently highlighted.
Yes, Village of Greenport is well-connected. The New York State Bicycle Route 25 provides an extensive path connecting Smithtown east to Orient Point and links with Route 48 in Southold Town. Additionally, the Seaview Trails network boasts 57 miles of bicycle trails throughout Southold Town, offering further exploration opportunities.
Absolutely. Orient Beach State Park offers biking trails and is known for its unique blend of salt marshes and red cedar forests. You can also find Inlet Pond County Park, which features trails through woodlands and an observation platform for birdwatching, making it a great stop during a ride.
The road cycling routes around Village of Greenport vary in length to suit different preferences. You can find shorter loops, such as the Shelter Island Heights loop from Town of Shelter Island at 14.3 miles (23 km), which takes about 1 hour 8 minutes. Longer options include the Shelter Island Heights loop from Silver Beach at 28.4 miles (45.7 km), taking around 2 hours 3 minutes, and even a difficult 102-mile (164 km) route for extended rides.


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