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United States
New York
Suffolk County

Shinnecock Hills

The best walks and hikes around Shinnecock Hills

11

hikers

12

hikes

Hikes around Shinnecock Hills explore a landscape of rolling hills, coastal wetlands, and rare maritime grasslands. The region, located in Southampton, New York, features trails that wind through protected nature preserves and along the shores of Shinnecock Bay. The terrain is generally flat with minimal elevation, making it accessible for most ability levels.

Best hiking trails around Shinnecock Hills

  • The most popular hiking route is Tuckahoe Woods Preserve via Paumanok Path loop — Southampton, a 2.2 mile (3.6 km)…

Last updated: May 17, 2026

#1.

Penny Pond Loop Trail

8.18km

02:07

50m

50m

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Moderate

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate
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Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

1

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Tips from the Community

Zachary
April 29, 2025, Paumanok Path - Penny Pond

The Paumanok Path meets the Penny Pond loop trail at this junction. Both are well-marked. The trail around Penny Pond takes you to an observation blind right on the water, where you can picnic and watch for wildlife.

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The Paumanok Path traverses a lovely series of rolling hills and ponds here. The path is well-marked and, for the most part, rests on a bed of soft pine needles. Be weary of chiggers in the warmer months.

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The two adjacent preserves, Big Wood Forest & Wolf Swamp Sanctuary, offer you to experience an abundance of natural life. From the red maple and tupelo swamp with frogs and native azalea to the oak-beech forest with century-old trees.

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Tuckahoe Woods Preserve, nestled in Southampton, is a serene natural oasis spanning 84 acres. It boasts lush woodlands, meandering trails, and diverse wildlife. This is a particularly special spot for birdwatchers, as the avian wildlife is plentiful.

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oliviakellis
October 10, 2023, Paumanok Path

The Paumanok Path is a scenic hiking trail spanning 125 miles across Long Island from Rocky Point to Montauk Point State Park. It showcases diverse landscapes, from forests to beaches, and the perfect opportunity to experience Long Island at its finest.

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Frequently Asked Questions

Are there many hiking trails to choose from around Shinnecock Hills?

Yes, there are a number of trails available. While this guide highlights the top 5, komoot features a selection of about 8 routes that explore the region's woodlands, wetlands, and coastal areas. All currently listed trails are rated as easy, making the area very accessible.

Are the hiking trails in Shinnecock Hills suitable for families with children?

Absolutely. The terrain around Shinnecock Hills is generally flat with minimal elevation gain, making it ideal for family outings. A great option is the Big Woods Preserve & Wolf Swamp Sanctuary loop, which is an easy 2.5-mile (3.9 km) walk through a mature forest.

Can I bring my dog on the trails?

Many preserves in the Southampton area are dog-friendly, but dogs are typically required to be on a leash. Policies can vary between parks and preserves, so it's always a good idea to check for signs at the trailhead before you start your hike.

What is the best time of year to hike in Shinnecock Hills?

Hiking is enjoyable year-round, but late spring is particularly beautiful. During this time, the rare maritime grasslands are in bloom with wildflowers and shrubs like beach plum, offering a unique scenic experience. Autumn also provides pleasant temperatures and colorful foliage in the woodlands.

Are there any circular or loop trails available?

Yes, most of the popular trails in the area are loops, allowing you to start and end in the same place without retracing your steps. For example, the Tuckahoe Woods Preserve via Paumanok Path loop is a 2.2-mile (3.6 km) circular route through scenic woodlands.

Where can I find a good hike along the coast or on a beach?

For a coastal experience, the Ponquogue Beach loop from Hampton Bays is an excellent choice. This 3.7-mile (6.0 km) trail offers beautiful views of the water. Additionally, Shinnecock East County Park provides access to an undeveloped barrier beach for those looking to explore the shoreline.

What are some of the most scenic spots or beautiful places to hike to?

The region is known for its diverse scenery. For panoramic views over Peconic Bay, head to the summit of Tuckahoe Hill within the Tuckahoe Hill Preserve. For serene marshland vistas, the trails in Big Woods and Wolf Swamp Preserves overlooking Sebonac Creek are ideal. The rare maritime grasslands in the Shinnecock Hill Preserve also offer a unique and beautiful landscape.

Is Shinnecock Hills a good destination for birdwatching?

Yes, it's an excellent area for birdwatching. The mix of forests, wetlands, and coastal habitats attracts a wide variety of birds. Pine Neck Sanctuary is particularly noted for its birding opportunities, with chances to see warblers, vireos, and various shorebirds along its trail overlooking Shinnecock Bay.

What should I know about parking at the trailheads?

Most preserves and parks have designated parking areas, but they can be small and fill up quickly, especially on weekends. Some trailheads are located in residential areas with limited street parking. It's always best to arrive early to secure a spot.

Are there any trails that explore the local towns or cultural sites?

Yes, you can combine hiking with local culture. The Art Center Southampton – Agawam Park with Monument loop is a pleasant walk that takes you through the heart of Southampton, past galleries and historic sites. Another option is the Village Hall – First Presbyterian Church loop, which also explores the charming village.

How difficult are the hikes around Shinnecock Hills?

The hikes in this area are generally considered easy. The landscape consists of rolling hills with very little significant elevation change. All of the routes currently featured in this guide are rated easy, making them suitable for hikers of all ages and fitness levels.

Most popular routes around Shinnecock Hills

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