The best road cycling routes around Head Of The Harbor
4.2
(10)
373
riders
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rides
Road cycling routes around Head Of The Harbor, a village on Long Island's North Shore, are characterized by scenic landscapes and diverse terrain. The region features winding country roads, picturesque waterfronts along Stony Brook Harbor, and rolling hills. Road cyclists can explore routes that offer views of the harbor and pass through areas with varied ecosystems.
Best road cycling routes around Head Of The Harbor
- The most popular road cycling route is Mount Sinai Harbor Loop, a 48.8 miles…
Last updated: October 5, 2026
7
riders
78.6km
03:24
480m
480m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
1
riders
91.6km
04:04
710m
710m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
17
riders
47.3km
02:24
430m
430m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
4.0
(1)
15
riders
67.0km
03:03
630m
630m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
10
riders
26.5km
01:12
210m
210m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Tips from the Community
This beach is a nice spot for swimming, with restrooms, playground equipment, campsites and a refreshment stand. The water usually passes cleanliness standards.
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These wetlands are designated as a state conservation area due to their important habitat for coastal fish and wildlife. Keep an eye out for abundant birds, including endangered species like the short-eared owl and pie-billed grebe. Although you're less likely to see them, the mudflats, channels, and wetlands also provide vital habitat for fish and marine invertebrates.
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Avalon Nature Preserve, in Head of the Harbor, captivates with its diverse ecosystems. Spanning 216 acres, it features woodlands, wetlands, and serene trails, providing a peaceful haven for nature enthusiasts.
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Great view of the harbor as you peer across to Centerport. There is a small pier and beach that you can sit on and listen to the waves or watch the boats pass.
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Gorgeous views all around, very quiet and secluded. It'd be a lovely spot to have lunch and read a book. The roads there are very hilly and the town it's in is quite wooded and forest-y; it doesn't feel like the usual strip-mall suburbs of Long Island.
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This lake was formed by retreating glaciers. It is the largest freshwater lake on Long Island.
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The lighthouse sits on the northern tip of Old Field. It was first built in 1823, then rebuilt in 1868. The U.S. Coast Guard took it during WWII but gave it back to the Old Field community afterwards.
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Frequently Asked Questions
How many road cycling routes are available around Head Of The Harbor?
There are over 45 road cycling routes around Head Of The Harbor, offering a variety of options for different skill levels and preferences.
Are there road cycling routes suitable for beginners in Head Of The Harbor?
Yes, Head Of The Harbor offers 13 easy road cycling routes. These paths are generally less demanding, making them ideal for those new to road cycling or looking for a more relaxed ride.
What kind of terrain can I expect on road cycling routes in Head Of The Harbor?
Road cycling in Head Of The Harbor is characterized by winding country roads, picturesque waterfronts along Stony Brook Harbor, and rolling hills. You'll find a mix of flat sections and routes with significant elevation gain, offering diverse experiences.
Are there challenging road cycling routes with significant elevation gain?
Yes, many routes in the area feature rolling hills and notable elevation changes. For example, the Stony Brook University to Brentwood loop via Northport includes over 700 meters of elevation gain, providing a good challenge for experienced cyclists.
What are some scenic road cycling routes in the Head Of The Harbor area?
The region is known for its scenic beauty. The Mount Sinai Harbor Loop offers beautiful harbor views, while the Cordwood Park – Avalon Nature Preserve loop from Smithtown takes you through diverse ecosystems including woodlands and wetlands.
Can I find circular road cycling routes around Head Of The Harbor?
Yes, many of the road cycling routes in Head Of The Harbor are designed as loops, allowing you to start and end at the same point. Examples include the Mount Sinai Harbor Loop and the Stony Brook University to Brentwood loop via Northport.
What natural attractions can I see while road cycling in Head Of The Harbor?
While cycling, you can enjoy views of Stony Brook Harbor and pass by areas like Avalon Nature Preserve, known for its diverse ecosystems. The Arthur Kunz County Park, with its tidal creeks and forests, is also nearby.
Are there any historical landmarks or points of interest along the road cycling routes?
Yes, cyclists can encounter historical landmarks such as the Old Field Point Light, a historic lighthouse located on the northern tip of Old Field, which is featured on routes like the Old Field Point Light – Cordwood Park loop from Smithtown.
What do other road cyclists enjoy the most about road cycling in Head Of The Harbor?
The area is highly rated by the komoot community, with an average score of 3.75 stars from more than 5 reviews. Cyclists often praise the scenic landscapes, winding country roads, and the diverse terrain that offers options for various ability levels.
Is there a dedicated paved path for cycling in the Head Of The Harbor area?
Yes, the Setauket-Port Jefferson Station Greenway Trail is a 3-mile paved path that winds through old-growth forests, farmlands, and meadows, connecting to Stony Brook University and county parks. It's an excellent option for a smooth ride.
What is the best time of year for road cycling in Head Of The Harbor?
The region offers pleasant cycling conditions through much of the year. Spring and fall typically provide comfortable temperatures and beautiful scenery, while summer is also popular, though it can be warmer. Winter cycling is possible but may require checking for road conditions.
Are there routes that connect to other significant areas or parks?
Yes, some routes connect to or pass by notable locations. For instance, the Stony Brook University to Brentwood loop via Northport links to Stony Brook University, and the Setauket-Port Jefferson Station Greenway Trail connects to various county parks.
Most popular attractions around Head Of The Harbor
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