In the heart of Manhattan, Madison Square Park is more than just a green retreat—it’s a window into New York City’s storied past.

On this tour, we’ll uncover how the park became a gathering place for the city’s elite, relive its most notable moments, and explore the surrounding buildings that have witnessed history unfold. 

From there, we’ll journey up Fifth Avenue, diving into the fascinating backstories of some of New York’s most iconic landmarks.

This is your insider’s guide to Old New York and the lasting impact it has on the city today. Join us for an unforgettable walk through time.

Places you will see and discover

Just some of the locations and so much more:

.: The Gilded Age

Find out the backstory that shaped the area and how it came to be the playground of the wealthy

.: Madison Square Park

How it came to be and notable moments.

.: Notable monuments and moments

Discover corrupt politicians who scored statues in the park and notable moments that have occurred over the park’s history.

.: The Flatiron building

Built to fit an odd sized block of land, it became an icon of the skyline.

.: Empire State Building

An icon built on the site of one of New York’s most popular hotels.

.: New York Public Library

Built on the site of a reservoir, it has come to be a city favorite, featured in countless movies and tv shows.

Not everything is in the highlights, everyone loves a good surprise! We’ve included:

• Pop-Up tour points on local insights and food
• Hidden gem spots and activities
• Handy travel tips and insights to enhance your journey.

Inclusions and exclusions

The tour price includes access to all tour points. Our tour points have free entry, unless otherwise specified.

One minute expert

The Ylore Travel app is your gateway to adventure. Discover curated tours, explore points of interest, or design your own itinerary. Become an instant travel expert in just one minute.

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Start your adventure

1 Add the tour to your Tours list

2 Reorder the itinerary if you need

3 Select your mode of travel for the tour with walking, bike and vehicle

4 Press Play

Start

The tour start point is nominal. It’s your tour, your way. 

You can re-order tour points and start close to you. Long press the tour marker and adjust up/down in the itinerary. Stop and restart the tour at any time. It’s yours to keep.

Mid way changes

Running out of time to see it all? You can delete tour points part way through a tour.

End

Tour your way. You can choose to end the tour as per the tour itinerary OR you can delete tour markers that aren’t of interest or don’t fit your time schedule. Simply long press the tour marker.

Authentically us

We believe in authenticity. Each tour we have walked and photographed. Got an update? Tell us at hello@yloretravel.com with the name and ID of the tour.

Key points

Transport

We create our tours with accessibility in mind. Our goal is to start tours close to public transport. You will need to make payment for any public transport you use.

Comfort

With so much to see, comfort is key. Wear appropriate shoes and dress for the weather. 

Battery

Consider bringing a portable charger to ensure your phone stays powered throughout, and after your tour.

Safety

Navigating unfamiliar locations can be chaotic. It's essential to stay safe by always looking both ways before crossing the street and obeying traffic laws. You are responsible for your own safety.

Travel usually involves crowds, particularly during peak times. Keep calm and carry on.

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