4.6
(11)
102
riders
16
rides
Touring cycling around Head Of The Harbor, New York, features a landscape characterized by its waterfront views of Stony Brook Harbor and winding country roads. The region includes rolling hills, diverse ecosystems, and natural preserves such as Avalon Nature Preserve and Arthur Kunz County Park. These features provide varied terrain for cyclists, ranging from serene coastal paths to more challenging routes through forested areas.
Last updated: July 2, 2026
4.5
(4)
37
riders
37.5km
02:09
110m
110m
The Bike loop from Port Jefferson offers a diverse touring cycling experience, blending the hilly, winding sections of the Setauket-Port Jefferson Station Greenway with the largely flat and easy North…
5.0
(1)
7
riders
43.6km
02:43
400m
400m
The Old Field Point Light – Cordwood Park loop from Port Jefferson is a fantastic touring cycling route that delivers stunning coastal views and a good workout. You'll pedal through…

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3.0
(2)
12
riders
11.8km
00:46
130m
130m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
8
riders
50.2km
03:04
420m
420m
The Avalon Nature Preserve – Old Field Point Light loop from Smithtown offers a fantastic touring cycling adventure, blending natural beauty with coastal charm. You'll pedal through diverse landscapes, from…
5.0
(1)
7
riders
53.4km
03:22
560m
560m
Embark on a truly challenging touring cycling adventure with the Cordwood Park – Avalon Nature Preserve loop from Port Jefferson. This difficult route spans 33.2 miles (53.4 km) and climbs…
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The Setauket-Port Jefferson Station Greenway Trail, or Setauket Greenway, is a 3-mile paved path on Long Island’s north shore. It connects scenic old-growth forests, farmland, meadows, business districts, Stony Brook University, and county parks. The trail features a mix of wooded sections and occasional sunny spots, with several road crossings, and some short sections that pass through utility corridors and sand pits.
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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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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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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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There are over 20 touring cycling routes in and around Head Of The Harbor, offering a variety of options for different skill levels and preferences.
You'll find a diverse landscape for touring cycling, characterized by winding country roads, rolling hills, and beautiful waterfront views of Stony Brook Harbor. Routes often pass through diverse ecosystems, including woodlands and wetlands, providing varied scenery.
Yes, Head Of The Harbor offers several easy touring cycling routes. For instance, the Bike loop from Setauket is an easy 7.3-mile (11.8 km) trail that provides a pleasant ride through local scenery, ideal for a relaxed outing.
For more experienced cyclists seeking a challenge, there are difficult routes available. The Arthur Kunz County Park – Meadowlark Park loop from Smithtown is a difficult 38.5-mile (61.9 km) route with significant elevation gain, offering a rewarding ride through varied terrain.
Many touring cycling routes around Head Of The Harbor are designed as loops. Examples include the Avalon Nature Preserve – Old Field Point Light loop from Smithtown, a moderate 31.2-mile (50.2 km) path, and the Cordwood Park – Hilltop Meadow loop from Stony Brook, which is 23.5 miles (37.8 km).
Routes often feature beautiful natural settings and historical landmarks. You can pass by the Old Field Point Light, a historic lighthouse, or explore areas near the Avalon Nature Preserve and Arthur Kunz County Park, which offer diverse ecosystems and serene natural settings.
Absolutely. Many routes offer stunning waterfront views of Stony Brook Harbor. The Avalon Nature Preserve – Old Field Point Light loop from Smithtown, for example, provides views of the Old Field Point Light and the surrounding coastal landscape.
The spring and fall seasons generally offer the most pleasant conditions for touring cycling in Head Of The Harbor, with milder temperatures and beautiful foliage. Summer can also be enjoyable, though it may be warmer, while winter cycling is possible but requires appropriate gear for colder weather.
While specific parking details vary by route, many trailheads and parks in the Head Of The Harbor area, such as those near Avalon Nature Preserve or Arthur Kunz County Park, typically offer designated parking areas for visitors. It's advisable to check specific route details for the most convenient parking.
Public transport options to specific trailheads might be limited, as many routes traverse scenic, less urbanized areas. However, some routes, like those connecting to the Setauket-Port Jefferson Station Greenway Trail, may be more accessible from local towns with public transport links.
The touring cycling routes in Head Of The Harbor are highly rated by the komoot community, with an average score of 4.5 stars from over 10 reviews. Cyclists often praise the picturesque landscapes, the blend of winding country roads and waterfront views, and the opportunity to explore diverse natural preserves.
Yes, some areas like Arthur Kunz County Park feature trail systems that link to the Long Island Greenbelt Trail, offering potential extensions for longer touring routes and further exploration of the region.


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