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Routes
Hiking trails & Routes
United States
New York
Suffolk County
Northwest Harbor

Chatfields Hole via Northwest Path

Easy

4.7

(3461)

12,458

hikers

Chatfields Hole via Northwest Path

00:50

3.20km

20m

Hiking

Hike an easy 2.0-mile (3.2 km) route through diverse woodlands to Chatfield's Hole, a glacial kettle hole in the Grace Estate Preserve.

Last updated: February 26, 2026

Waypoints

A

Grace Estate Preserve

Highlight • Forest

Grace Estate Preserve offers over 500 acres of water and woods for exploring. It has miles of trails and nice views of Northwest Harbor, and it's ideal for bird watching, …

Tip by

1

2.71 km

Two Holes of Water Park

Highlight • Lake

You can walk almost all the way around the ponds of this small park on wide, well-maintained trails that lead you deeper into the South Fork trail systems. There are …

Tip by

B

3.20 km

End point

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Way Types & Surfaces

Way Types

2.96 km

166 m

< 100 m

Surfaces

2.70 km

440 m

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

Powered by Foreca

Today

Monday 25 May

20°C

12°C

93 %

Additional weather tips

Max wind speed: 19.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

Where is the trailhead for Chatfields Hole via Northwest Path and is there parking?

The trailhead for this route is conveniently located at the kettle pond on Two Holes of Water Road in East Hampton's Northwest Woods. There is usually parking available directly at this location.

What is the difficulty level of this hike?

The Chatfields Hole via Northwest Path is generally considered to be of moderate difficulty. It's a manageable hike for most, but a moderate pace is suggested to fully enjoy the experience.

How long does it typically take to complete this trail?

Based on an average hiking pace, this 3.2 km (2-mile) route typically takes around 50 minutes to complete. However, you might want to allow extra time to enjoy the scenery, especially around Chatfield's Hole.

What kind of terrain can I expect on the Chatfields Hole via Northwest Path?

Hikers will traverse an oak forest interspersed with pitch pines and white pines. The Northwest Woods are known for their large stands of white pine, creating a soft, needle-covered path underfoot. The trail leads to a beautiful glacial kettle hole and freshwater wetlands.

What wildlife and natural features can I see along the way?

The area is a haven for wildlife, including painted and snapping turtles, green and bullfrogs, freshwater fish, raccoons, deer, belted kingfishers, and broad-winged hawks. The main natural feature is Two Holes of Water Park, which includes the kettle pond at the trailhead, and Chatfield's Hole itself, a significant glacial kettle hole and freshwater wetland.

Is the Chatfields Hole via Northwest Path dog-friendly?

Yes, dogs are generally welcome on this trail. Please ensure your dog remains on a leash to protect the local wildlife and ensure a pleasant experience for all hikers.

Are there any fees or permits required to hike this trail?

No, there are typically no fees or permits required to access the Chatfields Hole via Northwest Path, as it is part of East Hampton's preserved open space.

What is the best time of year to hike this route?

The trail offers diverse scenery year-round. Spring and fall are ideal for pleasant temperatures and vibrant foliage. Winter hiking can also be a unique experience, offering a quiet, snow-dusted landscape, though conditions may vary.

Does this trail connect with other hiking paths?

Yes, the area around Chatfield's Hole is part of a network of trails. This route specifically follows the Northwest Path and also intersects with sections of the Paumanok Path and Fosters Path, offering opportunities for longer explorations.

What should I know about hiking in the Grace Estate Preserve?

The Chatfields Hole via Northwest Path is located within the Grace Estate Preserve, an important conservation area. Please help preserve its natural beauty by staying on marked trails, packing out all trash, and respecting wildlife. The preserve was one of East Hampton's first open-space acquisitions for public use.

Is this a loop trail or an out-and-back route?

This specific route, 'Chatfields Hole via Northwest Path', is designed as a loop trail, allowing you to experience different sections of the preserve without retracing your steps.

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