One 'Short' Day in Midtown - A Self-Guided Walking Tour

What to do in 16 hours in the middle of Manhattan?
by Lauren Hauptman

Short, of course, is relative. And with so much to do in the Big Apple, one day must be relegated to one area. There’s no better area than the one that contains the best shopping, theater and architecture in the world: Midtown Manhattan. We’ve set out an ambitious 16-hour tour within the roughly 2-square-mile area from 40th Street on the south to 59th Street on the north, and Third Avenue on the east to Ninth Avenue on the west.

Whatever your preferences, this itinerary is very adjustable, and the time guidelines are pretty rough. No one is timing you: Expand or skip at will. Want to spend more time shopping? Do some credit damage in the Fifth Avenue stores (not a big shopper? the shop stops we suggest are still worth a peek). Want to explore the park? Wander farther north for a green while. Raining? Spend time in the shops, buildings and museums along the way. All our recommendations are free unless otherwise noted.

Regardless of how you tweak your day, there’s a lot to do, see and eat, so get up early, put on some comfortable yet stylish shoes, and get going: Gotham awaits.


8 am: Grand Central Terminal ( & Breakfast Part 1, 42nd Street and Park Avenue)
Do as the locals do, and meet at the information booth under the four-faced clock in the center of Grand Central Terminal (as New Yorkers call it). Look around: The sunlight streaming in through the soaring arched windows gives the marble-laden Beaux Arts interior an other-worldly glow often missed by those running to catch the train to their Westchester and Connecticut suburbs.

Head down to the lower-level Dining Concourse for the first part of your breakfast. Get a cup of coffee (and a nibble if you’re really hungry; some bread and cheese from the fabulous Grand Central Market on the Main Concourse is also a nice holdover until Breakfast, Part 2) to drink while you explore Grand Central (as New Yorkers also call it).

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Surprisingly great shops abound, as do stunning architectural features. Back in the main concourse, be sure to find yourself a spot where you won’t get knocked over by rushers-by, look up at the zodiac ceiling, and feel free to gasp. Star-gazing will never be the same to you.

The entire station is full of wonderful history and secrets; alas, some discoveries will have to wait for your next visit. Do make a quick stop at the Transit Museum Store in the Shuttle Passage, which has some of the best New York subway souvenirs in the city. In 2011, Apple took over the eastside balcony, so this is, arguably, the coolest place ever to check your e-mail (extra-handy if your hotel charges for WiFi) or buy an iPad.

[Seasonal note: Roughly from Thanksgiving to the end of December, the building’s Vanderbilt Hall hosts the Grand Central Holiday Fair, one of the best gift fairs we’ve ever seen; other happenings are held here throughout the year.]

9:15 am: Park Avenue & Breakfast Part 2
Exit the north side of Grand Central, up the escalators, through the Met Life Building, out the doors onto 45th Street. Across the street you will see two tunnels; take the one on the right, which is East Helmsley Walk, which will let you out on Park Avenue, where you will continue walking north.

Head north up Park Avenue, which is a wide boulevard usually centered by colorful plant life and, sometimes, interesting sculpture. You will pass the famous Waldorf-Astoria Hotel and pretty St. Bartholomew’s Church. Just past St. Bart’s, make a right onto 51st Street and head east. When you reach the southwest corner of 51st and Lexington Avenue, look up and to your right for a great view of the top of the Chrysler Building.

Continue east to Third Avenue, where you will see Ess-A-Bagel (831 Third Ave., 51/52) staring back at you from across the street. Here are, arguably, the best bagels in New York and, therefore, the world. Ask for whatever’s hot and get it with butter, or a shmear of cream cheese to go. Be grateful if they give you a hard time, as this is how New Yorkers show love. Walk and eat at the same time, turning left out the door, then right on 49th Street, heading west to Fifth Avenue.

10 am: Saks Fifth Avenue (611 Fifth Ave., 49/50)
Stand in front of Saks, look across street at Rockefeller Center. If it’s December, you’ll see the famous tree at the end of the Promenade; other seasons offer beautiful foliage of their own. We will spend more time in Rockefeller Center later, so feel free to pop into Saks briefly.

10:15 am: Fifth Avenue, east side
Exit through one of Saks’ front doors and turn right; walk up the east side of Fifth Avenue, heading north toward Central Park. This is one of the world’s major shopping meccas, but the first building you’ll encounter after Saks is St. Patrick’s Cathedral; if you like churches, stop inside. You’ll pass a plethora of high-end stores on your way to the park.

[Tip: Department stores are the best places to use the bathroom; the nicer the store, the nicer the bathrooms — usually.]

As you continue up Fifth Avenue, stops may include Trump Tower (long past its heyday); a peek down 57th Street, home of the world’s most well-known luxury brands; the New York flagship of Apple Store, accessed through a giant Louvre-esque cube in front of former FAO Schwarz.

[Tip: The Apple Store is a great place to check your e-mail if you don’t have free WiFi in your hotel]

If you are hungry, buy a pretzel, hot dog and/or chestnuts from one of the ubiquitous street vendors. Chances are they won’t taste great, but it’s something you need to do anyway.

11:15 am: Central Park
Designed near the end of the 19th century by Frederick Law Olmsted, “the Park” is an idyllic pastoral paradise in the chaotic city. You could spend a week just wandering around, eat all your meals and do everything but sleep there (though some do that, too), but, alas, there’s only time for a quick peek today.

[Note: If you do want to spend a little more of your short day here, highlights of the southern part of the park include the Central Park Zoo (time it to be there on the hour or half-hour to see and hear the George Delacorte Musical Clock), Wollman Rink in winter, the carousel and rowing on the lake (not in winter) by the Boathouse.]

11:30 am: Fifth Avenue, west side
Once you extricate yourself from the park, pretend you’re Madeleine, and run through The Plaza Hotel (Fifth Avenue at Central Park South). Head south on Fifth Avenue. A quick stroll through the ground floor of old-line New York department store Bergdorf Goodman just south is warranted (note: The men’s store is across the street), if only to see the wealthiest New Yorkers buying their upscale accessories under the beautifully, wonderfully ornate ceilings. As you continue south on Fifth Avenue, make time for a stop into Manhattan’s other uber-store, Henri Bendel (712 Fifth Ave., 55/56). Bendel’s famous Lalique windows, brown-and-white-striped everything (the cosmetic and travel cases are world-renowned), and unusual accessories and jewelry make this one of our favorite stores.

Continue south on Fifth Avenue, passing flagship store after flagship store. If you’re not a shopper, try to appreciate the architecture. Make a right on 53rd Street. On the right (north) side of the street is the Museum of Modern Art (11 W. 53rd St.), which reopened in 2004 to mixed reviews following a major renovation. Entrance to MoMA is expensive, though if you can stand huddling with the masses, Fridays from 4–8 pm are free. Cross the street to the MoMA Design Store (44 W. 53rd St.), which is phenomenal for arty souvenirs and minimalist MUJI items. Turn right out of the store onto 53rd Street, then make a right back on to Fifth Avenue.


12:30 pm: Rockefeller Center (Fifth Avenue, 49/50)
Rockefeller Center is especially fun in the winter, when you can watch the ice skaters go round and round (if you’re really lucky, an Olympian will be doing spirals, or a marriage proposal will be under way on the ice). Have lunch in the Rockefeller Center Concourse overlooking the rink or in the gardens that replace it during other seasons. There are myriad restaurants ranging from food court–style options to the upscale Sea Grill. Get to the concourse level by taking the glass elevators from the street on the north and south sides of the plaza, or through 30 Rock (30 Rockefeller Center, the tall building behind Prometheus) to see its beautifully muraled Art Deco lobby.

2 pm: Radio City Music Hall (Sixth Avenue [Avenue of the Americas], 50/51)
On the west side of Rockefeller Center at Sixth Avenue is Radio City Music Hall, the Art Deco home of the Rockettes and any number of visiting acts. There are also tours and, in December, the famous Christmas Spectacular.

Continue south on Sixth Avenue, and grab a cupcake for dessert at the Magnolia Bakery (of Sex and the City fame) location at 49th Street (northeast corner). Continue south on Sixth, and turn left on 47th Street to the stretch known as Diamond Jewelry Way, named for the, well, diamond and jewelry stores that line the street. Walk east to Fifth, then down the other side of 47th back to Sixth. Ogle at the jewelry lining the windows; avoid the sidewalk diamond-hawkers who are there to convince you life would be so much better with a few more carats (well, it would). Continue west on 47th Street to Broadway.

2:45 pm: TKTS Booth (47th and Broadway, under red steps; opens at 3 pm for evening performances)
This glass-encased booth is where you will buy discounted tickets for your evening activity: Broadway! Get on line and be ready with a prioritized list of shows you want to see (available performances are shown on the TKTS signs). Ask the other theater-goers for recommendations; you will meet both locals and tourists while you wait. When you get to the window, conduct your business quickly and decisively so you don’t annoy your new friends on line behind you.

4 pm: Times Square/42nd Street
Pretend you are a local, and shake your head in disbelief at Disneyfication of Times Square. Note the news ticker on the One Times Square (The New York Times) Building (where the New Year’s ball drops), the NASDAQ board, the giant Coke bottle, and all the fantastically, overwhelmingly bright lights and signs.

Turn left onto 42nd Street heading west, and make a right on Fifth Avenue.

4:15 pm: New York Public Library (Fifth Avenue, 40/42)
Take your photo with the giant stone lions, named Patience and Fortitude, who guard the front of the library. You’ll be tempted to rest your weary soles on the steps, which will be crowded on a nice day, but there’s a better option behind the library.

4:30 pm: Two Options

1. Bryant Park (behind library)
Rescued from a dilapidated, drug-riddled fate nearly two decades ago, Bryant Park has become a midtown haven with lots of public tables and chairs among the pretty greenery. Winter hosts yet another skating rink; summer welcomes lots of outdoor events, including the popular and free Monday-night movies. Purchase a coffee or other beverage, and relax until dinner.


2. Empire State Building (350 Fifth Ave., 33/34)
A bit south of the rest of our itinerary — just a quick stroll south on Fifth Avenue to 34th Street — you will find the Empire State Building. Currently the tallest building in New York City, it offers awe-inspiring panoramas from observation decks on the 86th and 102nd floor (there are entrance fees for both). The Art Deco tower is often lighted in different colors at night in honor of an event, holiday or sports team.


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6 pm: Dinner (5 pm if Tuesday)
There are so many restaurants in the Theater District. Be sure to choose ahead and make a reservation to avoid disappointment, hunger and/or bad food. Two of our favorite pre-theater eating spots:

Toloache (251 W. 50, Broadway/8) This is not just one of the best pre-theater restaurants, but one of our favorites in the whole city. Chef/owner Julian Media serves authentic Mexican dishes twisted with unusual flavors. Who knew guacamole is better with fruit? Yes, fruit. Trust us. The Guacamole Frutas is a taste sensation, as is the Quesadilla de Huitlachoche y Trufas, a heavenly disc of Mexican mushrooms, manchego cheese, corn and black truffle. The impressive sheet of tequilas is a bonus.

Cascina Ristorante (647 Ninth Ave., 45/46) Well-priced house-made pastas and stone-oven pizzas shine here, especially when paired with wine from the owner’s own vineyard in Italy. Start with the Focaccia al Rosmarino (focaccia bread with rosemary and olive oil), and ask for the pre-theater menu for an extra good deal.

7:30 pm: Broadway Show (for 8 pm curtain; 6:30 pm for 7 pm curtain if Tuesday)
Arrive at your show in plenty of time to use the restroom and take your seat, so you don’t upset any locals by being late.

10:30 pm (approx)–midnight: Post-Theater
Revel in the glow of a wonderful show that changed the way you think of modern theater, or take the opportunity to lambast the indulgent director, inarticulate playwright or past-her-prime star over a post-theater drink or dessert. Both are available at perennial favorite Joe Allen Restaurant (326 W. 46, 8/9). Don’t lambast too loudly, as there’s a good chance your show’s cast or crew is there, too, as this is still a celebrity hangout.

Alternatively, if you didn’t include a visit earlier in the day, this is a great time to visit the Empire State Building, which is open until 2 am every day. What better way to end your very long Short Day in Midtown than by taking in the twinkling night lights from high above the City That Never Sleeps?
Lauren Hauptman is a native New Yorker who is temporarily a long-term tourist in San Francisco. She has been a contributing editor and writer for WHERE San Francisco and Pulse Guides, and is an editorial and creative services consultant for numerous other publications and organizations through . She believes New York is the center of the universe.

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