Macy's
34th Street Herald Square
Macy's is the originator of this tradition and back in the early days, the original Macy's window displays were mechanized and powered by store employees on treadmills! Today they actually offer two different displays, both classic NYC Christmas stories. 

On 34^th Street they highlight favorite scenes from The Miracle on 34^th Street movie: Kris Kringle complaining to the shop owner that the line up of reindeers is incorrect in his display, Susan watching the Thanksgiving parade from the apartment window and the dramatic finale in the courtroom with Santa’s letters overflowing on the judge’s desk.

On the Herald Square side delight in a retelling of the famous 19^th century letter to The Sun from young Virginia O'Hanlon questioning the veracity of Santa Claus.  The coolest thing about the windows this year is that they are made almost entirely of paper. If you look closely you will see it is all made of cut and glued paper. Fantastic!

Pit Stop:

While there head inside and upstairs to take a seat on Santa’s lap in their over the top North Pole. If you need a break you can grab a seat in Greeley Square, they have food kiosks ringing the seating area and usually a festive light display of their own.  

Pit Stop:   

If the kids are getting tired, you may want to take a break on the stairs outside the NYPL Stephen Schwartzman Building just a few blocks north.  A photo with Patience or Fortitude would make a great holiday photo for your cards, or pop into the lobby to check out their beautifully decorated Christmas tree.  If they aren’t tired, walk over to Sixth Avenue to take a spin on the ice at the Pond, hit the carousel and the holiday market in Bryant Park or check out the train display at the Lionel Pop up store across the street.

Saks
Fifth Avenue at 49th St

These windows are opening tonight so I wasn’t able to see them on my window walk. While there, don’t miss the beautiful snowflakes that light up and twinkle down on the Fifth Avenue storefront.

Pit Stop:

Grab some hot chestnuts from the vendor on the corner and grab a seat on the stair at St. Patrick’s Cathedral (or inside the church sans the chestnuts.) Hungry? Hit the classic NYC coffee shop Prime Burger (East 51^st Street) for a good old fashioned egg cream. Or head directly across the street and brave the crowds at Rockefeller Center to see NYC’s most famous Christmas tree.

Bergdorf Goodman  
Fifth Avenue at 58th St
Bergdorf’s has fantastically opulent holiday windows again this year and while they're not very traditional and don't have Santa in them, kids may still be intrigued by their fairy-tale likeness. This year the overall theme is travel with trains, ships, and carriages (along with the zodiac and a bunch of other stuff, too.)  Don’t miss the giant UNICEF snowflake in the middle of the street.

Pit Stop:

Take a rest on Grand Army Plaza outside The Plaza hotel.  The fountain is decorated with Christmas Trees for a great holiday card photo a good sit down.  Walk across the avenue to FAO Schwarz for some holiday shopping or a rest on the outside plaza. 

Bloomingdales
59th St at Lexington Avenue
This year the Bloomies windows feature 100 digital screens assembled in a mosaic that will whisk you away to a dreamy and peaceful winter landscape.  Watch as the magical cardinal lights up the Christmas Trees one by one.  Mesmerizing.

Pit Stop:

If you can make it go over to Third Avenue to check out the windows of Dylan’s Candy Bar, kids will love the giant marshmallow people, then head inside and upstairs for some decadent hot chocolate.

To walk it all:

Head up town from Macy’s by starting on 34^th Street, wrap around the corner to Herald Square and then head east to Fifth Avenue to get to Lord and Taylor.  From there head up Fifth Avenue to Grand Army Plaza and head east to Bloomingdales – then take the bus or train back downtown.

If you are heading downtown, start at Bloomingdales head west to Fifth Avenue and work your way down toward 38^th street to hit all the stores. After Lord and Taylor head west to Herald Square. Don’t forget to see the 34^th Street side of Macy’s too. Grab the train back uptown.

An easier way to get in the spirit:

To see all the Holiday Windows on foot can be a long trek with kids. For an easier way to catch some Holiday magic, you can take the 5th Avenue bus downtown from 59^th Street (or even further uptown if you want.) You won't see the windows up close, but places like Cartier, Trump Towers and Armani themselves are decorated and seeing all the shoppers milling around the crowded streets you can pick up some Holiday cheer without getting stuck in the crowds.

For more holiday fun check out the Mommy Poppins Holiday Guide.