Best Holiday Things To Do On The Upper West Side

If you’re wondering whether the holiday season seems to start earlier with each passing year, you’re not alone. There are early deals in brick-and-mortar stores, and packages on stoops everywhere. The holiday season also provides a welcome opportunity for festive experiences. Traditional holiday events and activities are always a highlight of the year. With Thanksgiving, Hanukkah, Christmas, and Kwanzaa right around the corner, now is a good time to plan some holiday things to do. 

Whether you’re looking for visual or musical entertainment, animal or art exhibits, spectacular feats of human nature, eating, running, skating, or dancing, we’ve got you covered!  Here are 14 great ideas for things to do that will be sure to serve up the magic of a good old-fashioned New York City Christmas. Best of all, you can avoid a lot of pesky traveling with these tried and true reasons to get together with family and friends right here on the Upper West Side. Enjoy! 

Central Park Ice Skating – Wollman Rink – Season starts October 28, 2023

Wollman Rink, near the southeast corner of Central Park, New York City, will host a full day of activities on Saturday, October 28, when it opens for the season. Although hours vary, the rink is open every day thereafter, and you can bring your own skates or rent a pair. There is also a café on site.  This is the perfect place to do what New Yorkers have been doing since the 1950’s – get some exercise, while enjoying an iconic New York experience with friends, family, or a date. So get going! The closest entrance is at 59th Street and 6th Avenue.  Wollmanrinknyc.com

Shop & Skate at Bryant Park’s Winter Village – Oct. 27, 2023 – March 3, 2024

A little farther south is something for the entire family. Bryant Park’s Winter Village is located on 40 – 42^nd Streets, between 5^th and 6^th Avenues, and is open early to late.  With around 180 kiosks for shopping and eating, this annual event also brings a whole host of activities to its 17,000-square-foot space. There are igloos in which to eat, an ice skating rink that’s free to use (if you bring your own skates), and an open-air holiday market that has crafts and gifts from around the world.  Bryantpark.org

New York Marathon – November 5, 2023

New Yorkers love to get out and cheer the runners brave enough to take on their New York City Marathon! This incredibly exciting event brings together over 50,000 runners from around the world.  The 26.2-mile race makes its way through all five boroughs. Those of us not running also count it as one of our most active days of the year.  Stake out a good viewing spot in advance, pack your snacks and extra layers of clothing and get to your chosen location early. The NYC Marathon is on November 5th, and coincides with the end of Daylight Savings Time, when clocks “fall back” an hour. This means we will all be well rested, and in good cheering spirits! 

On the Friday before the Marathon – November 3rd starting at 5 p.m.- there will be an opening ceremony that features the Parade of Nations. This is a showcase for runners from all over and ends with a spectacular show of fireworks over the finish line. The New York Road Runners Club notes that spectators can watch from the Grand Stand seating by entering the Park at Central Park West and 63^rd Street.

Big Apple Circus – November 8, 2023 – January 11, 2024

The Big Apple Circus is a one-ring circus that began in 1977 as a more intimate alternative to the traditional three-ring circuses. It boasts “an eye-popping, jaw-dropping extravaganza of imaginative acts and wondrous spectacles that give a fresh take on the classical circus tradition”. Performances include 14 circus and variety acts, as well as dance and music. There are no animals in this all-new show. The show runs approximately 2 hours and 15 minutes and promises a great way to spend an evening with kids.  Located at Damrosch Park at Lincoln Center between Amsterdam & W. 62nd Street. The circus runs from November 8 through January 11, 2024. bigapplecircus.com

AMNH – “The Secret World of Elephants”

Have you ever wanted to see a life-size model of an elephant? Wondered about an elephant’s trunk? Thought about how an elephant processes between 300 and 500 pounds of food a day. Did you know that elephants use very low sound waves to send messages through the ground to other elephants?  How did elephants evolve anyway? And how are they similar to humans? If these sound like interesting questions, then this new exhibit at the American Museum of Natural History is for you. The exhibits showcase the ways in which humans and elephants have shared the planet and co-existed for thousands of years. It opens Monday, November 13^th, and can be seen daily, except when the Museum is closed on Thanksgiving Day and Christmas Day. An additional ticket is required to visit the exhibit, although museum members can visit for free. Amnh.org

Light Show at Saks 5th Avenue – November 23, 2023 – early January 2024

If there is one sight guaranteed to stop busy New Yorkers and out-of-towners in their tracks, it’s the Saks Fifth Avenue Annual Light Show. This festive show unites and delights scores of pedestrians on neighboring sidewalks, as they crane their necks to get a look at the front of the Saks building (611 5th Avenue between 49th & 50th Streets). The light show has thousands upon thousands of LED lights dancing on the building, and these are perfectly synchronized to holiday music. The show lasts under 5 minutes and repeats several times an hour. It is spectacular and well worth a look. Saks also has terrific holiday window displays.

Macy’s Thanksgiving Day Parade – November 23, 2023

Pretty much everyone has had the chance to see snippets of the Macy’s Thanksgiving Day Parade on TV over the years. Seeing it live and in person is a different kind of magic! Since its inception in 1924, the Parade has delighted kids of all ages. Who doesn’t love giant balloons, floats, live music, marching bands, TV personalities, scenes from Broadway shows, and Santa Claus? This year, as usual, the annual parade will begin at 9:00 a.m. at 77th Street & Central Park West, before heading downtown to 34th Street at Macy’s Herald Square.

The parade’s giant character balloons are typically inflated the night before, in preparation for their Thanksgiving Day appearances.  If you would like to see the Balloon Inflation Event up close and personal, it is set for the afternoon of Wednesday, November 22, 2023 near 77th Street & Central Park West.

George Balanchine’s Nutcracker – November 24-December 31, 2023

If you haven’t already had the pleasure, this really is one of those annual holiday traditions you might not want to miss.  Tchaikovsky’s music, Balanchine’s choreography, and the combined talents of dancers, musicians, stagehands, and children from the School of American Ballet guarantee an always mesmerizing performance. Sumptuous sets and costumes enhance this timeless classic. The Nutcracker begins the day after Thanksgiving and runs through New Year’s Eve. Tickets for afternoon and evening performances can be found at nycballet.com.

Columbus Circle Holiday Market – November 28 – December 31, 2023

Check out this outdoor holiday pop-up market. It’s got rows and aisles of booths filled with unique foods, jewelry, art, home goods, and other unusual items. It runs from 11 a.m. to 7 p.m. daily. This is typically a festive experience, chock-full of good-humored vendors, New Yorkers, tourists, and holiday cheer.

Tree Lighting at Rockefeller Center – November 29, 2023

Although the tree itself arrives early in November, The Rockefeller Center Christmas Tree comes into all its glory when it is lit (around 9:00 p.m.) on the Wednesday after Thanksgiving.  If you’d like to be a part of this captivating experience, plan to get to the Rockefeller Center area early. Join the crowds for what always feels like something unique, magical, and spectacular.

New York Philharmonic Handel’s Messiah – December 12-16, 2023

First performed in 1742 in Dublin, Handel’s Messiah is a well-recognized part of the New York City Holiday Tradition. Perhaps best known for its famous Hallelujah Chorus, performances of Handel’s Messiah are invariably beautiful and memorable. These can be found in several of the majestic churches and choral spaces around the city throughout the month of December. The New York Philharmonic, in particular, offers a performance not to be missed.

Christmas on Fifth Ave: The Boys of St. Thomas Choir with Juilliard MAP String Ensemble – Thursday, December 14, 2023

Check out the wonderful music and beautiful setting that is St. Thomas Church at 1 W. 53rd Street. This hour-long concert is scheduled for Thursday, December 14^th from 5:30-6:30 p.m.

Jazz at Lincoln Center: Big Band Holidays – December 13-17, 2023

In this annual event, the Jazz at Lincoln Center Orchestra performs new and traditional arrangements of classic favorites such as “Winter Wonderland”, “Deck the Halls” and “Dreidel, Dreidel, Dreidel”. Shows will be held from December 13 to 17^th at the Rose Theater, located at Broadway and 60th Street.

New York Philharmonic: Holiday Brass – December 16-17, 2023

An annual holiday tradition for the past 25 years, these family-friendly concerts are scheduled for 2:00 p.m. on Dec. 16-17th at the David Geffen Hall at Lincoln Center.  Get ready for a festive afternoon.