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Routes
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United States
New York
Suffolk County

Head Of The Harbor

The best walks and hikes around Head Of The Harbor

4.7

(36)

237

hikers

40

hikes

Hiking around Head Of The Harbor, New York, offers diverse landscapes for outdoor exploration. The region is characterized by coastal corridors with views of Long Island Sound, dense woodlands, and freshwater wetlands. Hikers can explore areas with picturesque ponds and boardwalks, with varied terrain including gentle hills suitable for different ability levels. Stony Brook Harbor defines the village's northern border, providing scenic vistas and waterfront areas.

Best hiking trails around Head Of The Harbor

  • The most popular hiking route is…

Last updated: May 12, 2026

5.0

(1)

3

hikers

#1.

Setauket-Port Jefferson Station Greenway Trail

8.73km

02:21

110m

90m

Embark on a moderate hike along the Setauket-Port Jefferson Station Greenway Trail, a paved path that stretches 5.4 miles (8.7 km) with an elevation gain of 373 feet (114 metres).…

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Moderate

2

hikers

Discover the David Weld Sanctuary Trail, an easy hiking route that offers a diverse landscape shaped by glacial activity. This 1.7-mile (2.7 km) path involves a gentle elevation gain of…

Easy
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Hike the easy 0.9-mile Avalon Nature Preserve Green Trail through tranquil woodlands, featuring diverse ecosystems and unique art installati

Easy

2.15km

00:34

20m

20m

Hike the easy 1.3-mile Red Trail in Caleb Smith State Park Preserve, gaining 64 feet in about 34 minutes through peaceful forest.

Easy

4.32km

01:08

30m

30m

Hike the easy 2.7-mile Lower River Trail in Sweetbriar Nature Center, gaining 93 feet of elevation in just over an hour.

Easy
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Popular around Head Of The Harbor

Road Cycling Routes around Head Of The Harbor

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MTB Trails around Head Of The Harbor

Tips from the Community

oliviakellis
May 25, 2024, Caleb Smith State Park

Nestled in the heart of Smithtown, Caleb Smith State Park Preserve spans 543 acres of diverse habitats that offer picturesque views throughout the seasons. As one of four state nature preserves on Long Island, it provides a serene escape from the daily hustle and bustle. The park's passive use policy protects local plant and wildlife populations, ensuring a quiet, peaceful environment for visitors.

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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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Frequently Asked Questions

How many hiking trails are there in Head Of The Harbor?

There are over 20 hiking trails around Head Of The Harbor, offering a variety of experiences from easy strolls to moderate loops through diverse landscapes.

What do other hikers enjoy the most about hiking in Head Of The Harbor?

The area is highly rated by the komoot community, with an average score of 4.8 stars from more than 30 reviews. Hikers often praise the diverse natural settings, including coastal views, dense woodlands, and picturesque ponds, as well as the well-maintained trails.

Are there easy hiking options suitable for families or beginners?

Yes, Head Of The Harbor offers many easy hiking options. For instance, the Avalon Nature Preserve loop — Head of the Harbor is an easy 2.9-mile trail that explores a diverse preserve with coastal views and forested areas, perfect for a family outing.

Are there any challenging hikes in Head Of The Harbor?

While most trails are easy to moderate, some routes offer varied terrain with more elevation changes. For a moderate challenge, consider the Blydenburgh County Park & Forestwood Park loop — Smithtown, which is 5.5 miles and features varied terrain through woodlands and around a lake.

What is the best time of year to hike in Head Of The Harbor?

The trails in Head Of The Harbor are enjoyable year-round. Spring brings blooming flora, summer offers lush greenery, autumn showcases vibrant fall foliage, and winter provides a serene, quiet experience, especially in areas like Avalon Nature Preserve or Caleb Smith State Park.

Are there circular walks available in the area?

Yes, many of the popular routes in Head Of The Harbor are circular. Examples include the Avalon Nature Preserve loop and the Caleb Smith State Park loop, allowing you to start and end at the same point.

Can I bring my dog on the hiking trails?

Many parks and preserves in the Head Of The Harbor area, such as Blydenburgh County Park, are dog-friendly, typically requiring dogs to be on a leash. It's always best to check specific park regulations before you go.

Are there any trails with good viewpoints or scenic spots?

Absolutely. The Avalon Nature Preserve offers a coastal corridor with views of Long Island Sound. Caleb Smith State Park features views of Willow Pond and a 140-foot hill called High Point. Blydenburgh County Park also provides scenic views, particularly on the west side of Stump Pond.

What kind of wildlife can I expect to see while hiking?

The diverse habitats in Head Of The Harbor, including coastal areas, woodlands, and wetlands, support a variety of wildlife. Hikers may spot various bird species, deer, and smaller mammals. The Avalon Nature Preserve, for example, is known for its diverse flora and fauna.

Is there parking available at the trailheads?

Yes, most major parks and preserves in the Head Of The Harbor area, such as Avalon Nature Preserve, Caleb Smith State Park, and Blydenburgh County Park, provide designated parking areas for hikers.

Are there any interesting places to explore near the hiking trails?

Beyond the trails, you can explore several nearby attractions. Consider visiting the Setauket-Port Jefferson Station Greenway Trail for more walking, or the historic Old Field Point Light. The Arthur Kunz County Park also offers additional natural areas to discover.

Are there trails suitable for a longer day hike?

For a longer day hike, the Blydenburgh County Park – Blydenburgh County Park Lake loop from Hauppauge is a good option, covering over 5.7 miles around Stump Pond with varied terrain. Nissequogue River State Park also offers longer sections, including parts of the 32-mile Long Island Greenbelt Trail.

Can I access the trailheads using public transport?

While some areas might be accessible via local bus routes, many trailheads in the Head Of The Harbor region are best reached by car. It's advisable to check local Suffolk County transit schedules for specific routes and stops near your desired starting point.

Most popular routes around Head Of The Harbor

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