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

Despite being smaller than almost everything around it, including the humongous MetLife Building that dwarfs it from behind, the Grand Central Terminal is just so gorgeous and palatial-looking that it still manages to be the centerpiece of the whole East Side of Midtown Manhattan. Passing from here to Union Square, our self-guided tour is bound to introduce you to some of New York City’s most iconic landmarks!

Walking to the Empire State Building is a must, especially for the unique views of all the amazing sites NYC has to offer. The observation deck at the 102nd floor, which is a modern addition with unobstructed floor-to-ceiling windows, allows for only a small number of guests at a time, so it’s not overcrowded. You can walk all the way around and see the city from every angle!

Another quintessential NYC experience, Macy’s flagship location in Herald Square is a great place to shop if you’re looking to do that. And even if you’re not planning on buying anything, walking through at least part of it is a fun activity, just to say you've visited. On a few of the uppermost floors, they still have original escalator steps which are rather interesting.

Swing by the Madison Square Garden arena and the incredibly photogenic Flatiron Building before finally reaching Union Square – a nice place to be if you have no agenda and just want some place to hang out or people-watch. Despite the neighborhood having changed significantly over the years, it still attracts artists, performers, activists, students, chess players, locals and tourists, and is home to an amazing farmers market.

Make sure to bring your walking shoes, and select a nice day for wandering around. Our self-guided walk will do the rest, so why not give it a shot? ;)
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Grand Central Station to Union Square Map

Guide Name: Grand Central Station to Union Square
Guide Location: USA » New York (See other walking tours in New York)
Guide Type: Self-guided Walking Tour (Sightseeing)
# of Attractions: 6
Tour Duration: 2 Hour(s)
Travel Distance: 3.8 Km or 2.4 Miles
Author: doris
Sight(s) Featured in This Guide:
  • Grand Central Terminal
  • Empire State Building
  • Macy's in Herald Square
  • Madison Square Garden
  • Flatiron Building
  • Union Square
Grand Central Terminal

1) Grand Central Terminal (must see)

With 44 platforms and 67 railway tracks on two levels, the Grand Central Terminal is the largest train station in the world. It opened to the public in 1871, as part of the New York Central Railroad, when long-distance passenger trains were the most popular mode of transportation in the U.S.

The station was remodeled in 1913 upon which it got its current name, Grand Central Terminal. The ornate building features Beaux-Arts style with Corinthian columns and grand staircases. The ceiling on the top level has a beautiful blue fresco decorated with gold constellations by French artist, Paul Hellou. The lower level has a restaurant, called the Oyster Bar, which has vaulted ceilings with terracotta Gustavino tiles that form the support for the vaults.

In 1994, Grand Central Terminal was remodeled again – with lower ceilings and space for a retail mall and food court. It is now not only a transportation hub, but also an important tourist destination in New York City.

Why You Should Visit:
A great attraction to visit when the weather is wet, as it is mostly indoors. Awesome in size and lots of interesting details to look at.
Loads of eateries and quaint shops to check out between the commutes and trains.

Oyster Bar on the lower level offers a huge selection of oysters and other seafood.
Don't forget to visit the Whispering Gallery just outside the Oyster Bar. Stand in opposite corners and you can clearly hear the opponent. Quite fun!

Opening Hours:
Daily: 5:30am-2am
Empire State Building

2) Empire State Building (must see)

For 40 years, the Empire State Building had been the tallest building in the world until 1972 when it lost the title to the World Trade Towers. After the September 11th, 2001 attack on the WTC, it became the tallest structure in New York City once again.

The building was designed by William Frederick Lamb of the Shreve, Lamb and Harmon architectural firm. It has a simple art deco style typical of the high rise structures in pre-World War II New York. The simplicity was dictated by budget constraints, the time limit for construction and the city zoning laws. 3400 workers were involved in the project, including immigrant European workers and Mohawk metal workers from reserves in Canada. It was completed in one year and 45 days. Upon its inauguration in 1931, the building was declared one of the seven wonders of the modern world by the American Society of Civil Engineers.

Empire State building has 102 floors and stands 1,250 feet high. An iconic part of the New York City skyline, it has been a designated Historic Landmark since 1986.

Why You Should Visit:
The views on a clear day or evening are breathtaking. If you aren't afraid of heights, you should definitely buy a ticket to the 86th-floor observatory or the 102nd floor (for a little extra) to get a spectacular 360-degree view that is centrally located. It's an open deck, so great for pictures, and with binoculars (mounted there) you can look at places around!

Check the weather forecast before you visit. If it's not a clear day, DO NOT GO.

Opening Hours:
Daily: 8am-2am
Macy's in Herald Square

3) Macy's in Herald Square

Since opening in 1902, the legendary Macy's flagship store in Herald Square has been a shopping paradise for visitors and an architectural icon and landmark of New York City. A store like no other, it has continued to be a trendsetter right from the inception, and was the first building to have a modern-day escalator. With 1,250,000 square feet (116,000 m2) of retail space under one roof, Macy's is one of the largest department stores in the United States. It was added to the National Register of Historic Places and was made a National Historic Landmark in 1978.

The store covers an entire city block with 11 levels of the latest fashions, featuring a dazzling array of designer brands, the choice and quality of which never fail to amaze. Restaurants and cafes can be found throughout the store and exciting events are held here almost every day.

The place is known for its great sales, especially compared to some other major New York City department stores. If you crave some refreshment or feel like having a bite, there are plenty of dining options to consider, from casual, fast-food eateries (such as Starbucks, Tabo Noodles, The Rooster’s Crow, etc.) to the more refined sit-down restaurants (Herald Square Cafe, Rowland's Bar & Grill, Stella 34 Trattoria), so there's no reason for you to go hungry or thirsty while at Macy's.

Weekdays before lunch are the least crowded times to visit.
The lower floors tend to be more crowded than the upper floors.
There is a package and coat check at the Visitor Information Center on the Mezzanine Level.
You can ask cashier to have your purchases shipped straight to your home.
International shoppers can get a discount card at the Visitor's Center for 10% off most purchases.
Madison Square Garden

4) Madison Square Garden

One of the most famous venues in the world, Madison Square Garden hosts each year over 300 sporting events, musical performances and other gatherings. The arena was built in 1968 on the site of the demolished Pennsylvania Railway Station, and was the first structure of this sort to be placed atop a railway station. The venue incorporates a large indoor theater, expo center for trade and car shows, two cafes and a 9,500 feet terrace.

Madison Square Garden is the longest active sporting facility in New York City, hosting basketball, ice hockey, and boxing matches on a regular basis. On two occasions, in 1972 and 1994, the Stanley Cup Finals and NBA Finals were held here simultaneously. Some of boxing’s biggest fights were held at Madison Square Garden as well, including the first Muhammad Ali – Joe Frazier bout.

Based on the annual ticket sales, MSG is the third biggest music venue in the world which, throughout its history, has seen practically all the top performers in the world. In 1972 Elvis Presley made history becoming the first entertainer to sell out four consecutive shows at MSG. The March 3 1988 concert by Michael Jackson is considered to be the greatest concert ever held here. The Garden is also the only venue at which each of the four former members of The Beatles played solo concerts after the breakup, with John Lennon’s final concert at MSG taking place just before his murder in 1980. Sir Elton John has played MSG 62 times – more than any other artist, and Justin Bieber claims the record for selling out Madison Square Garden the fastest of any artist – two shows for his 2012 Believe tour sold out in just 30 seconds.

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.

Go to the Madison Square website and check what events are taking place during your visit!
The facility tour is very interesting, but make sure there are no events scheduled for the day you want to take it, because it may not be offered.
Flatiron Building

5) Flatiron Building

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!

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.

Opening Hours:
Daily: 10am-5pm
Union Square

6) Union Square

Named so for being an intersection of New York's once two major thoroughfares – Bloomingdale Road (today's Broadway) and the currently extinct Eastern Post Road, Union Square has been the scene of many gatherings (social, political and other) throughout its long history.

In 1831, developer Simon Ruggles, the then owner of the surrounding lands, convinced the city to rename the area as "Union Square" and worked further with the NYC corporation to fence and develop the area, eventually turning it from a triangular to a rectangular form. At first, the place served as an entrance to New York City and was a residential neighborhood. After the Civil War, the area became a commercial hub. Famous rallies took place here including the patriotic rally with a quarter of a million people gathered in support of the Union troops after the fall of Fort Sumter during the American Civil War, and the historic Labor Day March, one of the first workers' demonstrations in the world that inspired workers movements all over the world. More recently, the square was a public gathering point for mourners after the terror attacks on September 11th, 2001.

Why You Should Visit:
Many interesting things worth checking out here, including: the central fountain, subway kiosks, equestrian statue of George Washington, Abraham Lincoln statue, a sculpture of Marquis de Lafayette, a sculpture 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.

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!

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