Visiting NYC During the Holiday Season: Exploring, Shopping, and Sightseeing- Itineraries for Two and Five Days

When I returned to New York as an adult, a new friend and co-worker said to me, "New York City around the holidays is absolutely magical. The lights, the store windows, the snow - it is all so exciting! Then January and February hit and you wish all the snow and cold would disappear!" As a native, and now, seasoned New Yorker, I couldn't agree more with her statement.

With the Thanksgiving holiday, New York turns into a snow globe of magic. If it snows, even more so. People bundled up and sloshing around make for a quiet and pretty New York City experience. Sure, people are still as feisty as ever, it is the holiday season after all, and shopping can be overwhelming even for those prepared with lists and gifts already purchased, but there is an overall sense of happiness and delight that comes with interacting with strangers.

The holiday season is also the busiest for New York City travel wise. Many visitors from around the world come to experience all that New York offers during the season including the endless shopping. EtsyNY team members know all about the shopping season, as they're currently and hurriedly making and packing goods for upcoming markets. 

In preparation for the season upon us, I've put together a list, with the help of native New Yorkers and current residents, of what is considered "must do/see" when visiting New York in December depending on a two-day/weekend or a full five-day/week schedule.

Two Days in NY: Holiday Windows + Handmade Markets at Bryant Park and Union Square + Rockerfeller Center

1. You definitely want to see the windows of Macy's at 34th Street and Lord & Taylor at 5th Ave. Both are gorgeous displays of holiday merriment.

2. If you're looking for unique and special gifts for the holidays, you want to make sure you visit the holiday markets set up at Bryant Park at 42nd and 5th Ave (on the map in point 3) and Union Square* at 14th Street. There are a few more open holiday markets such as Columbus Circle (no map available), but, these two I can confirm definitely have EtsyNY Team members selling their handmade and locally made wares.

If you're visiting Union Square, I highly, and I mean highly, recommend you stop at The City Bakery on 18th between 5th and 6th Avenues. They have some of the most decadent hot chocolate in the world. They also have these amazing homemade marshmallows that slowly melt by the temperature of the hot chocolate. YUM! As you're walking along this tour, you'll be glad to have one! 

Note on this map that Chelsea Market, which is hosting our annual Handmade Cavalcade, is listed on here and is the main focus on this map. Our Handmade Cavalcade is detailed below in the five day/week long schedule.

Note on this map that Chelsea Market, which is hosting our annual Handmade Cavalcade, is listed on here and is the main focus on this map. Our Handmade Cavalcade is detailed below in the five day/week long schedule.

3. Last, but not least, you'd have to see 42nd Street, or Times Square. Minutes away from there is Bryant Park, which is listed as a place to shop at their open holiday market; Grand Central Terminal, which is a beautiful building and also has trains to points North by way of Metro North; Rockerfeller Center, which has their famous Christmas Tree; and Radio City Music Hall, which currently has the Rockettes Holiday Show, "Christmas Spectacular" performing and is a must see.

Five Days in NY:  Holiday Windows + Handmade Markets at Bryant Park and Union Square + Rockerfeller Center + NY Botanical Garden Annual Train Show + Christmas Lights in Dyker Heights, Brooklyn

1 - 3.  See the three maps above and check out all of those options, as they're within walking distance from each other.

4. If you have a couple of hours to spend walking the grounds of the New York Botanical Garden, I recommend it. Currently, the annual Train Show (celebrating its 25th year!) is on display and it is perfect for children and adults! The trains have history and, as is New York City, are always evolving. I suggest you add this to your visit to Grand Central Terminal. You can purchase a ticket upon arrival, or on MTA's website to take the Metro-North Harlem local line to Botanical Garden Station.  It's a 20-minute train ride. The main entrance is across the street from the train station. You can't miss it!

Note: Almost directly across from the NY Botanical Garden is the Bronx Zoo. I'm not sure what they have on display for the Holidays, but if you're up there, you might want to make a full day and visit both locations. Remember, they're both large and you'll want to map your day accordingly if you do both.

Note: Almost directly across from the NY Botanical Garden is the Bronx Zoo. I'm not sure what they have on display for the Holidays, but if you're up there, you might want to make a full day and visit both locations. Remember, they're both large and you'll want to map your day accordingly if you do both.

5. Take a tour of the houses with Christmas light displays in Dyker Heights, Brooklyn! This is another option that requires some time and should be done in the evening. The lights go on at dark, around 5pm and stay on until around 9pm, give or take. The lights are definitely worth seeing around mid-December, if you can trek out to Dyker Heights. When I visited a few years ago, I did a bus tour through A Slice of Brooklyn that ran 3.5 hours, met at Union Square, and had a cannoli and coffee stop at the end. Their website (link above) has all details, including how to purchase tickets. Well worth the money in my opinion!

If you're not interested in spending that kind of money, you can take the subway to Dyker Heights, averaging around an hour each way and walk around the houses. There are some hills, so if you go the walking way, don't complain that you were not warned! Also, depending on when you go, it may be really cold, so you'll want to be bundled warmly if walking around.  Free Tours by Foot has some great instructions on how to best get there, along with streets and houses you want to make sure you see.

Note: Brooklyn is not scaled and therefore is not accurate. It should be wider.

Note: Brooklyn is not scaled and therefore is not accurate. It should be wider.

4. Last, but not least, you should head over to Chelsea Market. It's an institution and the High Line Park is around the corner. It has delicious eats and some great shops and most importantly, it will have the EtsyNY team Holiday Handmade Cavalcade (HHC) for the third year!

This year, the HHC will run for a full week - opening Monday, December 5th and closing on Sunday, December 11th. We are hosting a "Sip 'n' Shop" event on Thursday, December 8th between the hours of 6:30pm and 9:00pm. The event is sponsored by Brooklyn Brewery and will have alcoholic beverages for you to drink while shopping. The Handmade Holiday Cavalcade is a sought after event and we highly recommend RSVPing ahead of time for both the Cavalcade and the Sip 'n' Shop event. Shoppers without an RSVP will be charged $2.00 at the door.

If your holiday travels bring you to NYC at any time through the holiday season, we welcome you! Not to mention, you have a few ideas on how to spend your time. We hope you'll enjoy them, if you do decide to use these suggested schedules.

If you happen upon our glorious City during December 5th-11th, we hope you'll find your way into Chelsea Market and into the doors of our Handmade Holiday Cavalcade, leaving you with everlasting treasures from your holiday visit.

Happy Holidays!

Sara Stroman

Sara is a stationery maker and paper lover and runs S2 Stationery & Design. Since the young age of seven, she loved grabbing handfuls of deposit slips from banks and using the carbon copy paper to trace designs. In 2012, she traveled to Echizen, Japan to learn paper making from well known paper makers in the community with the blessing of their paper goddess. She also loves to travel and as you can see, doodling maps not set to scale.