Autumn on the Upper West Side: A Guide to Fall Festivals

Manhattan, skyscrapers and colorful trees Credit to Mikael Damkier

Fall in NYC’s UWS is a beautiful time to enjoy all the city has to offer. The leaves begin to change color and the sky gets a little bluer as sweater weather approaches. Apples from upstate, colorful squash, and chrysanthemums make their appearance at farmer's markets along curbs throughout the city. 

These are not the only harbingers of NYC’s autumn season; fall festivals begin popping up all over the city, especially on the Upper West Side. From pumpkin carvings to food tastings and even an old-fashioned county fair, you don’t have to leave the city to experience fun things to do with friends in the fall.

Uptown Night Market in Harlem

The Uptown Night Market in Harlem takes place from April through the month of October. There are over 80 vendors representing more than two dozen countries that reflect the diversity of Harlem and the city itself. Come celebrate the food, music, and art of different cultures starting at 4 pm every second Thursday of the month Under the Arches of Harlem at 701 W.133rd Street, 10 minutes from The Wallace.

The Great Jack O'Lantern Blaze

The Great Jack O'Lantern Blaze is an exceptional autumn festival that combines the magic of Halloween with artistic creativity. It’s held from September 13 through to November 17 at the historic Van Cortlandt Manor, the event showcases over 7,000 intricately hand-carved jack-o'-lanterns arranged into mesmerizing displays, including life-sized dinosaurs, a pumpkin Ferris wheel, and themed exhibits like the Day of the Dead. The festival's special effects, set against an all-original soundtrack, make it an immersive experience perfect for all ages. Visitors can also enjoy live pumpkin carvings and seasonal treats, making it a delightful celebration of autumn.

Located in Croton-on-Hudson, it's about a 50-minute drive from The Wallace Hotel, offering a scenic and festive escape from the city​.

The Harlem Meer Pumpkin Flotilla at Central Park

Every year Central Park hosts the Pumpkin Flotilla on The Harlem Meer. Free and fun activities include crafts, storytelling, scavenger hunts, and a “spirited” parade. The highlight of this event is the pumpkin carving. Once you’ve created the perfect jack-o-lantern watch them sail across the Harlem Meer at twilight as the enchanting flotilla unfolds. This fun family event is free and more information is found on the park's website. Pumpkins are not provided so be sure to bring your own soccer ball-sized pumpkin to carve and wear your costume too!

The New York Wine and Food Festival

Of course one of the biggest draws as fall festivities go is the New York Food and Wine Festival. This year's festival starts on Thursday, October 17th, and runs through Sunday, October 20th. Over 80 events are held all over the city as well as across the river in Brooklyn. One of the most popular close-to-the-UWS events is Thursday night’s dinner hosted by renowned chef Rocco DiSpirito at the Carlyle on Madison between 76th and 77th, just across the park from The Wallace, a 10-15 minute car ride.

The NYCWFF is a very popular festival and worth traveling a bit from the UWS to enjoy some once-in-a-lifetime festivities and flavors. Check out their website for more information and the schedule of events. 

OktoberFest NYC

OktoberFest NYC, held at Pier 15 from September 14 to October 27, is an incredible autumn festival that brings the lively traditions of Munich's Oktoberfest to New York City. Set against the backdrop of the stunning Brooklyn skyline, this festival features authentic German beers, bratwursts, and giant pretzels, along with live music and a festive atmosphere that truly captures the spirit of fall. Attendees can enjoy traditional Bavarian celebrations without leaving the city, making it a perfect local getaway during the autumn season.

Located at 242 W 76th St, The Wallace Hotel is just a 25-minute drive or a 50-minute subway ride from Pier 15, making it a convenient spot to experience the lively atmosphere of OktoberFest.

NYC’s Favorite UWS Luxury Accommodations

Fall in love with autumn in Gotham as you enjoy the festivals and festivities throughout NYC’s UWS in fall. Do it all conveniently during your stay at The Wallace. Our luxury hotel provides the perfect accommodations for your visit to NYC. Book your stay at The Wallace today.