If you find yourself in New York City, the city that never sleeps, this winter holiday season, you may be overwhelmed by the amount of things you can do. But, don’t worry! We’ve got you covered on what to do and where you to go — and you can walk to it all.
First, choose when you’re going to visit. New York City, and especially Midtown, where most of these sites are is very busy during the winter season. While the happy and excited people around you may add to your experience, too many people may mean that you can’t enjoy the grandeur to the fullest extent. If you can, choose to go on a weekday, rather than a weekend. Either, take this tour earlier in the day or later at night. The most popular times tend to be the afternoon and earlier evenings. Just know that these sights are naturally better at night when you can see the lights best — and because it’s winter, the sun sets earlier in the day.
Next, here’s a quick itinerary for a tour to walk and see the biggest and brightest sights in New York City, especially during the winter; just make sure you wear good shoes to walk in and layer up if the forecast is going to be cold.
Stop 1: Columbus Circle Holiday Market
Southwest corner of Central Park
The first stop on your walking tour is the Columbus Circle Holiday Market. Open for winter through Dec. 31 (but closed on Christmas day), this market is much smaller than the holiday market in Bryant Park. The size of the market gives more of a small-town vibe than much of the rest of New York and though it can get pretty crowded, it’s a bit easier to see everything than in Bryant Park. There are lots of places to shop for last minute gifts, get New York City souvenirs, and eat yummy, seasonal, and winter foods. If nothing else, you’ll get to look at lots of pretty and cool handmade crafts.
When you’ve finished at the market, walk away from Columbus Circle and walk down 59th Street from 7th Ave to Lexington Ave, which is about seven blocks to Bloomingdale’s (though these are New York blocks, so they’re a bit longer). As you walk, be prepared to take detours to see other buildings’ Christmas lights around you. Keep your eyes peeled, as you might miss something while you walk.
Stop 2: Bloomingdale’s
1000 3rd Ave.
Here you’ll stop at your first windows decorated for the holidays. This year, Bloomingdale’s windows are in partnership with Wicked (2024). As you walk up to the building, you’ll see pink and green lights in every window, distinct from the rest of the lights in New York, which are greens and reds. The windows closer to 60th Street are decorated pink for Glinda and the windows closer to 59th Street are decorated in green for Elphaba. There are a few hidden easter eggs in the windows, though don’t expect an overly wintery or holiday-themed display. The window at Bloomingdale’s is easy to miss but it’s a clever tie-in worth seeing. If you need a warm drink, pop inside Bloomingdale’s at their cafe or visit their Wicked pop-up store.
Before you walk away from Bloomingdale’s, take a look at the Louis Vuitton window on the corner of 59th and Lexington Ave — this window is decorated to match the holiday carousel display at the flagship store near Bergdorf Goodman. Don’t worry, you’ll pass Louis Vuitton on your way there.
Your next stop is going to be Bergdorf Goodman, but your walk includes some other fun windows for winter, as that’s what this area of New York is known for. Walk back towards Central Park and away from Bloomingdale’s along 59th street. On the corner of 59th and 5th Ave is the Dior store, decorated by an elaborate under-the-sea theme, with really beautiful details.
Next to Dior is the glass Apple store. It’s not really dressed-up for the winter, but it’s fun to see when you’re in New York. Now, walk down 5th Ave. As you walk, you’ll see small installations along 5th Ave with fun facts about the area. Most of them are red or have Christmas trees on them.
Stop 3: Bergdorf Goodman
754 5th Ave.
This year, Bergdorf Goodman used their holiday windows to celebrate the 200th Anniversary of Fifth Avenue. These stunning works of art may be the best windows of the New York City winter. There are two buildings for Bergdorf Goodman, and though it may be inconvenient, start at the farther side from where you’ve walked.
Each window celebrates something 5th Ave is famous for: signs, window shopping, the New York Public Library, Central Park, taxi cabs… you name it. The display is fabulous and though I don’t want to spoil it, take a good look at the window shopping window — it’s a little bit meta! The details and hidden secrets in these windows are truly incredible and worth taking time to look at.
As you walk down from 59th to 58th and cross back over to see the windows on the other side of the street, take another look down 58th at the Louis Vuitton store. In this area, on the corner of 58th and 5th, is a building dressed up like a giant stack of Louis Vuitton suitcases. Louis Vuitton dressed up this building’s scaffolding in their iconic patterns as part of a super cool promotional tactic — it’s the best scaffolding in New York City.
After you finish basking in the glory that is the Bergdorf Goodman winter windows (really, take some time with them; they’re fantastic!), continue walking down 5th Avenue towards Saks.
Stop 4: Saks Fifth Avenue
611 5th Ave
As you walk down 5th Ave, the sidewalk is going to get very busy. You’re going to walk closer to Rockefeller Center and the world-famous Christmas tree, so it’ll definitely be crowded — it is New York during Christmas time, after all.
The Saks holiday windows are a bit understated this year, especially compared to the way the rest of New York does the holidays; they’ve turned to cost-cutting measures following, “softer,” sales. Unfortunately, there is no light show as in previous years, but the window display is fun to look at. These windows hold less to the themes that the other windows have, but they have a nice wintery atmosphere with snow, crystals, and sparkles.
Stop 5: Rockefeller Center
45 Rockefeller Plaza
Turn around from the Saks windows and you’ll be staring directly at the Rockefeller Center Christmas tree. Though the decorations are pretty similar every year, the glory of the huge tree in New York City never gets old. It will be very, very crowded here. If you can get closer, it’s totally worth it; but fighting the crowds might not be. If it interests you, guests can go ice-skating here, although it can get pretty pricey and you have to pay a separate fee for renting skates (it is less expensive to skate at Bryant Park).
Stop inside Rockefeller Center for more shopping or food, including the latest location of lil sweet treat. There are also windows inside the building you can see the tree from.
From here is a straightshot to the most iconic of all, Macy’s. If you want, take a quick detour down 49th Street, away from Rockefeller Plaza, to FAO Schwarz, New York City’s world-famous toy store. There, the legendary toy store is celebrating 25 years of Jellycat, hosting the viral Jellycat diner. However, the wait for it can be pretty lengthy. For another suggestion: you can simply walk in and look around without waiting in line. The windows are also very cool, as FAO pulled out all the Christmas stops with their Jellycat set-up.
From FAO continue down to 6th Ave and up the street to see the Radio City Music Hall tree, scaled up the side of the building. If you’re able to get tickets, definitely stop to see the Rockettes dressed for winter. If not, the tree is pretty fun, too.
Stop 6: Bryant Park Winter Village
42nd St. and 6th Ave.
Walk back down 6th Ave towards Bryant Park for the annual Winter Village. This houses very similar vendors to the Columbus Circle market, but is at least twice the size with more options. There is a tons of food, drinks, and sweet treats here— including apple cider donuts.
Bryant Park has its own skating rink (which is less expensive than Rockefeller Center, as mentioned above) and it’s own Christmas tree. However, this area can get quite overwhelming, moreso in the winter, which you should be aware of in advance.
When you’ve finished Christmas shopping and wandering at Bryant Park, walk back onto 6th Ave and walk down to Herald Square.
Stop 7: Macy’s Herald Square
151 W. 34th St.
The most iconic of iconic holiday destinations: Macy’s Herald Square. Depending which part of winter season you visit during, the Thanksgiving turkey may still be on display above the main entrance. If not, every window is decorated with wreaths and bows for the winter. The Toys-R-Us windows are the best ones, with winter wonderland scenes featuring your favorite toys; some are interactive with have little games you can play.
If you’re brave enough to head for the winter crowds face on, go inside Macy’s to visit their holiday market. Again, it will be similar to Columbus Circle and Bryant Park, but there is fun, Macy’s-exclusive merch and you never know what you can find. Be careful— this is the biggest Macy’s ever and it is incredibly easy to get lost. If you’re up for it, stop at Santaland on the 8th floor and see the Macy’s Santa Clause. This will, of course, will also be crowded, with a line you could wait in for hours.
When you’ve finished at Macy’s, you can continue to explore downtown, or walk back up to Times Square. There’s an abundance of restaurants and things to do; you might happen on something fun while you walk, especially during the winter. That’s what New York City is all about: You intend to go one place and you end up stopping five times for something else fun on your way.
Hope this brings some extra winter holiday cheer to your winter season, while you walk New York City!
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