Grand Central Station to Union Square (Self Guided), New York

It may well be puzzling as to why New Yorkers use the terms “Grand Central Terminal” and “Grand Central Station” as if they’re the same thing... Here’s the secret: one is the rail terminal, the other is the post office attached to it, and the whole complex is busy enough that no one pauses to sort out the terminology.

The place's story began with Cornelius Vanderbilt, the 19th-century business titan, who collected railroads the way others collect postcards. After buying the Hudson River and New York Central lines in 1867, he fused them together and launched the construction of Grand Central Depot two years later.

The original depot, designed by architect John B. Snook, arrived in full Second Empire style—mansard roofs, ornate flourishes, and the confidence of a building that knew it had somewhere important to be. By 1874, it was ready for service. Trains glided into the Park Avenue Tunnel at 96th Street, slipping underground for the final approach. This solved the small problem of locomotives barreling down Manhattan streets, which city residents understandably found less than charming.

Then came 1902. A steam locomotive, blinded by smoke in the Park Avenue Tunnel, missed its signals and collided with another train. The crash sealed the depot’s fate. Within a few years, it was demolished, making way for the Grand Central Terminal we know today. The firms Reed & Stern and Warren & Wetmore teamed up to create the Beaux-Arts landmark—one focused on the functional layout, the other on the dramatic exterior.

Inside, the terminal doubled as an art gallery long before that was fashionable. The Main Concourse ceiling famously charts a glowing, backwards zodiac. The façade features the Glory of Commerce sculpture, a bronze statue of Vanderbilt stands guard out front, and cast-iron eagles keep watch over the whole scene.

Vanderbilt Hall regularly hosts exhibitions and seasonal events, while the Dining Concourse adds its own glow with rows of illuminated lightboxes. And every so often, the terminal surprises commuters with performance art—from choreographed flash mobs to unexpected installations—turning an everyday commute into something slightly cinematic.

Meet the undisputed champion of New York’s Art Deco era: the Empire State Building, a 102-story giant that rises over 1,450 feet above Midtown’s daily hustle. It once ruled as the tallest building on Earth; today it’s still impressive enough to hold a lineup of titles—seventh-tallest in New York, ninth in the United States, and still one of the tallest freestanding structures anywhere in the Americas.

Its name comes straight from New York’s proud nickname, the “Empire State,” and its streamlined design was the work of the Shreve, Lamb & Harmon architectural firm. Construction began in 1930, wrapped up just a year later, and replaced the former Waldorf-Astoria Hotel that once stood on the same block. From the start, the goal was simple: to build the biggest, boldest skyscraper the world had ever seen.

You’ll find this landmark in Midtown South, planted along Fifth Avenue between 34th and 35th Streets. Three observatories—on the 80th, 86th, and 102nd floors—offer wraparound views that make the city look like an architectural toy box. And thanks to its starring role in more than 250 films and TV shows, beginning with King Kong in 1933, the building’s Hollywood résumé is nearly as tall as the tower itself.

The exterior keeps things classic: Indiana limestone, granite, and clean geometric ornamentation that embodies Art Deco style without telling a story in symbols. The main entrance features metal doors framed by sleek vertical piers topped with sculpted eagles, along with a gold-lettered transom that proudly spells out the building’s name.

In recognition of its cultural and architectural significance, the Empire State Building was declared a New York City Landmark in 1980 and added to the National Register of Historic Places in 1986. Today, it remains one of Manhattan’s most enduring icons—an unmistakable marker on the skyline and an essential stop for anyone wanting to feel the full vertical spirit of New York.

Step into Herald Square, and you’ll find a retail heavyweight that has been dazzling New Yorkers since 1902. Macy’s flagship store isn’t just big—it’s the kind of big that makes you wonder if someone accidentally ordered the “extra-large city block” option. From the moment it opened, the place was already ahead of its time, proudly installing one of the very first modern escalators and setting the tone for every shopper who ever wanted to be whisked upward in style. With more than 1.2 million square feet packed under one roof, it still ranks among the largest department stores in the United States and earned the National Historic Landmark status back in 1978.

Inside, the scale only gets more impressive. Eleven levels of fashion, accessories, cosmetics, and designer labels unfold like a vertical universe of retail possibilities. You can wander from trendy streetwear to luxury couture in a single elevator ride, pausing along the way for anything from a caffeine boost to a sit-down meal. Macy’s hosts events throughout the year as well, so you may stumble upon a mini-concert, a product launch, or a holiday-themed spectacle when you least expect it.

Speaking of holidays, the store is practically a Broadway production in its own right every December. Its animated window displays along the Broadway side attract crowds who gather to admire whatever whimsical theme Macy’s dreams up for that season. Each year brings a fresh set of scenes, crafted with enough charm and detail to stop even the most hurried New Yorkers in their tracks.

And of course, part of Macy’s fame comes from its sales—serious discounts that often outshine those at other major department stores in the city. Whenever your shopping spirit needs a break, the food options scattered throughout the building make refueling easy, from quick bites to full meals. In short, this is one place where you can shop, snack, explore, and repeat without ever stepping outside.

Formerly resembling the Doge's Palace in Venice around 1900, the Altoid, which has since been relocated, stood proudly between Seventh and Eighth Avenues atop Penn Station. It holds a legendary status in the realm of sports, primarily due to its association with the thrilling sport of boxing. Today, as "The World's Most Famous Arena," it serves as the home for various renowned teams and hosts a myriad of events, both uplifting and controversial.

Within its hallowed walls, you can catch the electrifying NBA action of the Knicks, with notable figures like Spike Lee and supermodels gracing the courtside. The NHL's Rangers also call this iconic venue their home, and St. John's University's Red Storm showcases their talents here as well. In addition to sporting events, Madison Square Garden plays host to concerts, tennis tournaments, dog shows, political conventions, and even caters to enthusiasts of monster truck rallies and "professional" wrestling for those seeking a different kind of entertainment. For a more intimate experience, The Theater at Madison Square Garden presents shows that cater to diverse tastes.

A monumental $1 billion renovation, completed in 2013, transformed Madison Square Garden, upgrading nearly every aspect of the facility. Notably, two bridges were added, running parallel to the arena floor, offering a unique and elevated perspective for those seated high above.

Why You Should Visit:
Great arena with great amenities; a magnet for sports fans and live show aficionados alike. It boasts an amazing bowl-like arena that provides great viewing and good acoustics for whatever event you choose to attend.

Tip:
For a comprehensive list of upcoming events, it is advisable to explore Madison Square Garden's official website, where you can find a full calendar of captivating experiences awaiting your attendance.
While the facility tour is undoubtedly fascinating, it is important to check for any scheduled events on the day you plan to take it. The tour may not be available during days when events are scheduled.

Perhaps the most photographed edifice in New York City, the Flatiron Building owes its popularity and name to the unique design. The isosceles triangle-shaped building may not be as high as the nearby high risers of today, but when it opened its doors for the first time in 1901, it surely was one of the tallest in New York – 307 feet, 21 floors – rising like a Greek column, contrary to the other New York skyscrapers rising from a lower base block.

The Flatiron building was designed by Chicago architect, Daniel Burnham, as an office building for the Fuller Construction Company. Styled renaissance palazzo with beaux art detailing, it has the exterior of steel clad with terra cotta. Upon inauguration, the building was dubbed Burnham’s Folly by skeptics who doubted it would stand against strong winds. The design, however, has defied their misgivings and remained structurally sound till the present. Nowadays, it houses the headquarters of the McMillan Publishing Company.

The Flatiron building symbolizes New York City in picture postcards, television commercials and documentaries. It became a New York City landmark in 1966 and was added to the National Register of Historic Places in 1976.

Why You Should Visit:
The exterior of the structure is certainly unique and well worth a photo!

Tip:
At the crossroads between 5th Avenue and Broadway, this should be not the only attraction in the area. The district is trendy, and you can sit outside at one of the many local cafes or in Madison Square Park and just watch people go about their lives all day long. Alternatively, if you're more creatively inclined, the area has plenty of stores catering to those loving artistic design, as well as hip cafes and restaurants.

Union Square derives its name from its historical significance as the intersection of two major roads in New York City-Bloomingdale Road (now Broadway) and the Eastern Post Road (now extinct). Throughout its rich history, the square has served as a gathering place for various social, political, and cultural events. Initially, it functioned as an entrance to the city and a residential neighborhood. However, following the Civil War, it transformed into a bustling commercial hub.

The square witnessed notable rallies and demonstrations that shaped American history. One such event was the patriotic rally held after the fall of Fort Sumter during the Civil War, where a quarter of a million people gathered to support Union troops. Additionally, it was the site of the historic Labor Day March, one of the earliest workers' demonstrations in the world, which served as an inspiration for labor movements worldwide. In more recent times, the square became a central gathering point for mourners in the aftermath of the 9/11 terrorist attacks.

Today, Union Square remains vibrant and bustling, particularly during the summer months. Visitors can find people relaxing on the steps, enjoying lunch, and observing captivating street performances. Adorned with remarkable statues paying homage to prominent figures such as Gandhi, Washington, and Lincoln, the space hosts a remarkable year-round farmers market, operating on Mondays, Wednesdays, Fridays, and Saturdays, which showcases the talents of local chefs and offering an abundance of fresh produce.

Exploring Union Square offers a sweet experience of leisurely strolls, shopping, and indulging in delectable meals. To make the most of your visit, plan your itinerary around a satisfying meal or multiple dining experiences. It's worth noting that weekends tend to be crowded, so for a more relaxed experience, consider visiting during weekdays when the crowds are smaller.

Why You Should Visit:
Many interesting things worth checking out here, including: the central fountain, subway kiosks, the equestrian statue of George Washington, the Abraham Lincoln statue, a sculpture of Marquis de Lafayette and another of Gandhi, plus a year-round greenmarket where you can sample goods from local farmers. It also has several playgrounds, a lively holiday market, and benches you can sit on and watch a slice of New York go by. Cafes and restaurants also abound, so no need to worry about food.

Tip:
Stop by the Union Square station to read messages on the sticky notes left by passers-by, and feel free to leave one of your own!