NYC at Christmas Time: A Self-Guided Walking Tour of the City's MOST Festive Sites- The Adventuring Millennial
New York,  North America,  Walking Tours

NYC at Christmas Time: A Self-Guided Walking Tour of the City’s MOST Festive Sites

I don’t know about you, but I completely relate to Buddy the Elf when I think about NYC at Christmas time. The glittering lights, giant Christmas trees, and general cheer make me feel downright jolly!

Whether it’s your first or 50th time in NYC for the holiday season, there are a few sites you absolutely can’t miss: The Rockefeller Christmas Tree, the shop windows along 5th Ave, and Macy’s on 34th street!

I’ve already compiled a complete guide to the best Christmas Events in NYC for 2019 (which you can find HERE) but I thought it would also be fun to create a self-guided walking tour of Midtown Manhattan’s best Christmas decorations!

This 2-mile guide is designed to take you anywhere from a few hours to a full day! Use this guide to make sure you hit the NYC festive highlights + you might even learn a few fun facts along the way!

NYC at Christmas Time: A Self-Guided Walking Tour of the City's MOST Festive Sites- The Adventuring Millennial

Start: Bergdorf Goodman 5th Ave

754 5th Ave

This lux department store is the perfect place to start our tour! Take a yellow RW train to the 5th Ave Station and walk just a few minutes along 5th Ave until you reach Bergdorf Goodman.

Ok, so this store is actually two stores. One is just right across the street from the other. But the main store on the west side of Fifth Ave, which opened in 1928, features the best window displays. Each year, the team spends months planning and executing their impressive window displays. Walk around the store to admire the festive scenes before moving on to our next spot.

You don’t have to travel far! Just cross 57th street and you’re basically there. Hello Tiffany & Co!

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Stop 1: Tiffany & Co

727 5th Ave

NYC at Christmas Time: A Self-Guided Walking Tour of the City's MOST Festive Sites- The Adventuring Millennial

Even if you are just window-shopping, step inside this Tiffany & Co. The decorations usually continue inside + it’s just plain fun to pretend to be browsing the jewelry options. (I mean maybe you aren’t just browsing, but Tiffany’s is out of my budget for sure).

Before you move on, check out the fantastic window displays. Last year, the windows were decorated with futuristic robot-themed displays. Of course, everything was accented with the classic Tiffany-blue.

When you are ready for the next stop, continue along 5th Ave for five minutes until you reach Cartier. It’s pretty hard to miss. Oh and along the way, keep your eye out for other festive shops! I’m just calling out the best ones but most of the 5th Ave stores get in the holiday spirit!

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Stop 2: Cartier

653 5th Ave

NYC at Christmas Time: A Self-Guided Walking Tour of the City's MOST Festive Sites- The Adventuring Millennial

When I said you can’t miss Cartier, I meant it! This towering building is wrapped up like a present with a big red bow! Also, look for the glittering jaguars that are climbing up the side of the building.

P.S. The Cartier building is actually a 1905 mansion built for Morton F. Plant, the son of railroad tycoon Henry B. Plant. In 1916, Plant decided to move uptown as he felt the 5th Ave area was becoming “too commercial” (seem like we have a Charlie Brown connection)! Cartier purchased the building from Plant for $100 in cash and a Cartier double-stranded pearl necklace (worth $1 million at the time). Unfortunately for Plant, Kokichi Mikimoto’s cultured pearls soon came to the market and, when Plant sold the Cartier necklace in 1956, it was only sold for $150,000.

Once you get some pictures of the impressive Cartier building, let’s head to Radio City Music Hall! Can you already imagine the Rockettes getting in position for a kick line?

Walk southwest on 5th Ave towards 51st Street. Turn right on 51st Street and then turn left on 6th Ave.

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Stop 3: Radio City Music Hall

1260 6th Ave

NYC at Christmas Time: A Self-Guided Walking Tour of the City's MOST Festive Sites- The Adventuring Millennial

Even if you don’t step inside, you need to stop at Radio City during an NYC at Christmas time tour! The iconic high-kicking Rockettes have been performing in this music hall since 1932. Take in the gorgeous decorations on the front of the building and look for the Radio City Gingerbread House in one of the front windows.

Tickets are still available for many of the Rockette’s performances this season. (You can also look for discounted tickets on TodayTix). I first saw the Rockettes last year and it was a fun experience! My seats were cheap and I was pretty far from the stage, but the energy was worth it!

Once we leave Radio City, we aren’t going too far for our next stop. Head southwest on 6th Ave towards 50th St. Turn left towards Rockefeller Plaza and walk for about 0.1 miles until you see the iconic skating rink and Christmas Tree!

Stop 4: Rockefeller Center Christmas Tree

45 Rockefeller Plaza

NYC at Christmas Time: A Self-Guided Walking Tour of the City's MOST Festive Sites- The Adventuring Millennial

Would it really be Christmas in New York without the Rockefeller Center Christmas Tree? The first Rockefeller Christmas tree was raised in 1931 and the skating rink opened in 1936.

The 2019 tree is a Norway Spruce from the town of Florida, New York. Each year, Rockefeller Center gets tons of submissions for the tree. The choices are narrowed down until the perfect tree is selected, chopped down, and driven to NYC. After the Christmas season, the 2019 tree will be donated to Habitat for Humanity to be used as lumber.

On December 4, 2019, from 8-10 pm, the official Tree Lighting ceremony will be held. This is a huge televised event that is free to attend. But, just know that the viewing areas are available on a first-come-first-serve basis and it gets pretty packed.

If you happen to stop by Rockefeller Center before December 4, you will likely see the tree under scaffolding as they work hard to decorate it! After December 4, the tree will be lit under January 17, 2020.

Besides checking out the tree, you can watch (or participate) in the ice skating. There are no online sales for general admissions skating.

Take your time in Rockefeller Center. There are plenty of festive photo spots in the plaza. From here, we are heading to Saks Fifth Avenue, which is right behind the Plaza. In fact, you probably already saw the decorations as you walked around the plaza, but let’s head here for a closer look.

Walk through the Plaza towards 5th Ave. You will pass through the Channel Gardens which usually have festive decorations. Soon you will see the massive Saks Fifth Avenue display!

Stop 5: Saks Fifth Avenue

611 5th Ave

NYC at Christmas Time: A Self-Guided Walking Tour of the City's MOST Festive Sites- The Adventuring Millennial

Each year Saks Fifth Avenue is decked out like a glittering palace. Even if you visit during the day, you can still admire the impressive castle and festive window displays.

For 2019, Saks Fifth Avenue is partnering with Disney to present a Frozen 2 themed display! The windows and castle will be unveiled on November 25 with Idina Menzel to perform a few songs! Don’t worry if you miss this performance, the castle will dance and glitter each night afterward.

If you are getting a bit hungry, our next stop is perfect! We are now going to head to the Bryant Park Winter Village for another tree sighting and some festive food!

From Saks Fifth Avenue, walk south on 5th Ave. Once you reach 42nd Street, turn right. You will soon see the park!

Stop 6: Bryant Park Winter Village

40th and 42nd Streets & Fifth and Sixth Ave

NYC at Christmas Time: A Self-Guided Walking Tour of the City's MOST Festive Sites- The Adventuring Millennial

Welcome to the Bryant Park Winter Village! Honestly, you could spend the entire day here. There are a ton of festive activities and it is one of my go-to spots during the Christmas Season.

Here you will find another skating rink (that is actually free if you have your own skates, otherwise you just need to rent skates), a massive Christmas tree (which will be lit on December 5), holiday shops, eateries, and more! Spend some time strolling throughout the pop-up shops and checking out the food options. Step inside the greenhouse-like Lodge for a bar and more food options.

Some of my favorite eats in the Winter Village are:

Ok, I guess I really love sweets. But there are also plenty of savory options at the Winter Village, too!

If you want to end your tour here, I completely get it! There is a ton to do in Bryant Park, it’s close to Times Square, and you are near the BDFM subway. If you want to keep going, we are going to walk 0.5 miles to Macy’s on 34th St. Exit Bryant Park on 6th Ave and walk south. Once you reach 34th, turn right.

Stop 7: Macy’s 34th Street

151 W 34th St

NYC at Christmas Time: A Self-Guided Walking Tour of the City's MOST Festive Sites- The Adventuring Millennial

I know I said this about Rockefeller Center, but would it really be Christmas in NYC without a stop at Macy’s? This iconic department store really brings the Christmas cheer. Walk around the store to see the sparkling Believe sign and the welcoming Santa sitting over one of the entrances. Admire the massive window displays which were unveiled on November 21.

After taking everything in from the outside, step inside for even more cheer! The store is decorated beautifully with shades of blue and silver. Step to the 1st-floor mezzanine to write a letter to Santa. Just stick the letter in one of the red post boxes to donate to the Make a Wish Foundation.

From November 29-December 24, 2019 you can visit the Big Man himself in Macy’s Santaland! You can actually make your reservation in advance online if you want.

Alright, now that you’ve made it to 34th Street, our tour officially ends! I hope you’ve enjoyed seeing the city decked out in Christmas cheer! From the 34th Harold Square station, you can catch the BDFM or NQRW trains.

I have one last optional stop, but it is a 0.6-mile walk from Macy’s. If you are up for it, make your way to Broadway and walk south. Once you reach 27th St, turn left. You will see the entrance to the 230 5th Rooftop bar.

Bonus: 230 5th Rooftop Bar

230 5th Ave

NYC at Christmas Time: A Self-Guided Walking Tour of the City's MOST Festive Sites- The Adventuring Millennial

I know you might be thinking it is a bit cold for a rooftop bar, but hear me out. In the winter, this rooftop lounge features igloos so you can still enjoy the view without dealing with the wind.

These clear igloos are extremely Instagram-friendly and are available on a first-come-first-serve basis (so no reservations required). There is no entrance fee or minimum purchase to enjoy these igloos, but 230 Fifth has a pretty good happy hour Monday-Friday from 4:00 pm – 7:00 pm.


Now we have actually come to the end of this NYC at Christmas time self-guided walking tour! Are you heading to the city for the holidays? What are you most excited about?

If you are looking for more, check out these posts:

NYC at Christmas: The Complete Guide

How I Survived New Years Eve in Times Square

The Best Coffee Shops in NYC

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