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United States
New York
New York County

High Line, Chelsea, and Flatiron Loop

Easy

4.7

(8821)

18,414

hikers

High Line, Chelsea, and Flatiron Loop

01:42

6.74km

10m

Hiking

This urban adventure takes you through some of Manhattan's most dynamic neighborhoods, offering a blend of elevated green space, historic architecture, and vibrant street life. You'll stroll along the High Line, an elevated park with lush plantings and art installations, before exploring the bustling streets of Chelsea and the architectural marvels of the Flatiron District, including the famous Flatiron Building. It's an easy 4.2-mile (6.7 km) loop with minimal elevation gain, making it a perfect way to experience the city.

Planning your visit is straightforward; the High Line has multiple access points, some with elevators, ensuring accessibility for many. While the route can be walked in about 1 hour and 42 minutes, you'll want to set aside more time to truly explore the art galleries, boutiques, and food options along the way. Public transport is the easiest way to reach the starting point, as is typical for New York City.

The High Line itself is a remarkable example of urban renewal, transforming an abandoned railway into a beloved public park. This innovative design provides unique perspectives of the city, allowing you to observe the bustling streets from 30 feet above. The loop immerses you in a cultural hub, showcasing Chelsea's art scene and the Flatiron District's rich architectural history.

Last updated: June 9, 2026

Waypoints

A

Start point

Bus stop

Get Directions

1

472 m

The High Line – Southern Section

Highlight • Trail

If you leave the Highe Line, street stalls can be strengthened here at the typical NY snack, yummy!

Translated by Google •

Tip by

2

972 m

The High Line

Highlight (Segment) • Trail

A beautiful walkway park on the old upper Westside railway line closed in the 1980s and upgraded to the park in 2009-2016. There is plenty of seating and all kinds of architecture to admire. In addition, there is always the possibility to leave the park and enjoy the dining and supply options of the Chelsea Neighborhood.

Translated by Google •

Tip by

3

1.58 km

The High Line

Highlight (Segment) • Trail

In between, make an excursion to Chelsea Market.

Translated by Google •

Tip by

4

2.52 km

The Edge - Sky Deck

Highlight • Viewpoint

When it rains, the panes are only partially transparent. Even if the clouds shouldn't obscure the view, rain-covered glass surfaces reduce the view considerably. Since visiting the viewing terrace is quite expensive (over $40 in 2022), I would also have to wait for good weather.

Translated by Google •

Tip by

5

3.17 km

Madison Square Garden

Highlight • Monument

Madison Square Garden is New York's best-known and largest event venue. It can accommodate up to 20,000 spectators. Every year numerous concerts and sporting events take place there. It is the home ground of basketball team New York Knicks and the New York Rangers ice hockey team. There is also a cinema, a theater, a restaurant and a conference center inside.

Translated by Google •

Tip by

6

3.71 km

Greeley Square Park

Highlight • Monument

This triangular park was named after Horace Greeley, who founded the New York Tribune in 1841 and inspired many to move to California with his famous quote, "Go West, young man, go West." Additionally, you'll find a bronze statue here in his memory.

Tip by

7

4.56 km

Met Life Tower

Highlight • Monument

Adjacent to the Flatiron Building, Madison Square Park (opened in 1847) is a popular green oasis in the Flatiron District. The park extends from 23rd Street and 26th Street on 5th Avenue and Madison Avenue. Especially during lunchtime, many New Yorkers use the park for their lunch break.

In the 19th century, the Madison Square Park area was considered one of the most desirable addresses in the city. In the '90s it was a drug hub and an area best avoided.

Since 2001, thanks to the Madison Square Park Conservancy, much has been redesigned, events created for artists and a Shake Shack restaurant built in the middle of the park.

The park owes its name to James Madison, the fourth President of the United States.

lovingnewyork.de/sightseeing/parks-in-new-york/madison-square-park

Translated by Google •

Tip by

8

5.06 km

Broadway, New York City

Highlight • Settlement

Broadway - Went to the Broadway hit show in New York City called WICKED. Its full of fun and sing! It was fantastic and I will recommend it. Its about 2 1/2 to 3 hours long and you get a 15 break

Tip by

9

5.25 km

Union Square

Highlight • Monument

The square owes its name to the fact that it connects Broadway with Park Avenue. The park opened in 1839. Union Square is known for an impressive equestrian statue of George Washington, designed by Henry Kirke Brown and unveiled in 1856.

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Tip by

10

6.41 km

Museum of Illusions

Highlight • Monument

Interesting museum with many optical illusions, which children especially find funny and interesting. Admission is quite expensive (current prices at newyork.museumofillusions.us), but pretty much everything is expensive in New York anyway. And if the children refuse to go further, this museum is sure to be an alternative.

Translated by Google •

Tip by

B

6.74 km

End point

Bus stop

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Way Types & Surfaces

Way Types

6.70 km

< 100 m

Surfaces

3.62 km

1.80 km

1.29 km

< 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

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Today

Wednesday 8 July

28°C

18°C

0 %

Additional weather tips

Max wind speed: 8.0 km/h

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Frequently Asked Questions

How long does it take to complete the High Line, Chelsea, and Flatiron Loop?

This urban loop typically takes about 1 hour and 42 minutes to complete, covering a distance of approximately 6.7 kilometers (4.2 miles). It's a leisurely walk, perfect for soaking in the city sights.

Is this route suitable for beginners or all fitness levels?

Yes, this route is classified as easy and is suitable for all ages and fitness levels. The High Line portion, in particular, offers a flat and paved walking surface, making it very accessible.

What is the terrain like on this urban loop?

The terrain is entirely urban, featuring flat, paved pathways. The High Line itself is an elevated linear park built on former railway tracks, integrating sections of the original rails into the concrete paths. You'll be walking on smooth surfaces throughout the loop.

What kind of scenery and landmarks can I expect along the way?

You'll experience a unique blend of natural and urban landscapes. The High Line features meticulously designed gardens and public art installations. Along the route, you'll pass iconic New York City landmarks such as Madison Square Garden, Greeley Square Park, the Met Life Tower, and Union Square. You'll also get views of the city skyline, the Hudson River, and the Flatiron Building in the distance.

What is the best time of year to visit the High Line, Chelsea, and Flatiron Loop?

The High Line is beautiful year-round, but spring and fall offer the most pleasant walking temperatures and vibrant plant life. Summer can be hot and crowded, while winter provides a starker, yet still interesting, urban landscape. Weekdays are generally less crowded than weekends.

Is the High Line, Chelsea, and Flatiron Loop dog-friendly?

No, dogs are generally not permitted on the High Line itself, with the exception of service animals. For other sections of the loop that are on city streets and parks, leash laws apply. It's best to leave your furry friends at home for this particular route.

Do I need a permit or pay an entrance fee for this route?

No, there are no permits or entrance fees required to walk the High Line or any other public sections of this loop. It is freely accessible to the public.

Where can I find parking or access public transport for this route?

Parking in Manhattan can be challenging and expensive. It's highly recommended to use New York City's extensive public transportation system. The loop is easily accessible via multiple subway lines and bus routes, with many stops near Madison Square Garden, Union Square, and various High Line entrances.

Does this route intersect with other well-known paths?

Yes, this route incorporates sections of several city streets and paths. You'll find yourself on parts of Broadway, 5th Avenue, 6th Avenue, and 8th Avenue. It also includes significant portions of the High Line and passes near the Hudson River Greenway.

Are there any hidden gems or insider tips for exploring this area?

To avoid the busiest crowds on the High Line, consider visiting early in the morning or later in the evening. Explore the side streets of Chelsea for unique galleries and boutiques. Don't miss the opportunity to look down from the elevated perspective of the High Line for unique views of the city's architecture and street life.

Are there cafes or restaurants nearby?

Absolutely! This loop takes you through some of New York City's most vibrant neighborhoods, including Chelsea and the Flatiron District. You'll find an abundance of cafes, restaurants, and eateries catering to all tastes and budgets along Broadway, near Union Square, and around the High Line entrances.

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