The Coolest Things to Do in NYC This Fall Season

Instead of making pumpkin spice a personality trait, welcome the arrival of autumn in true NYC style.

Elsewhere | Photo by Luis Nieto Dickens
Elsewhere | Photo by Luis Nieto Dickens

When that Tuesday after Labor Day hits, New Yorkers are already fully committed to stanning fall.

And on top of delving into the quintessential aesthetic of cable knit sweaters, leaf peeping, and apple picking while breathing in that crisp Upstate New York air, we’re also kicking seasonal activities up a notch with everything that’s pumpkin spice adjacent (we’ll pass on the actual flavor though).

Whether it's dancing the night away at a Shrek-themed rave or shopping small at a vintage pop-up concept in Nolita, we pinky swear to set you up with must-try recs to welcome the arrival of autumn. Here are the coolest things to do in NYC this fall.

Oktoberfest New York
Oktoberfest New York

Friday, September 2 to Monday, October 31
The perfect excuse to spend the day sipping on huge steins of German beer, munching on brats and pretzels, and flexing your finest pair of matching lederhosen is this year’s Oktoberfest activities at Pier 15’s Watermark. Here, enjoy live music, tons of themed goodies, a decked-out 3,500-square-foot venue, and stellar views of the Brooklyn skyline. With events happening seven days a week until October 31, there’s plenty of opportunities to snag a free RSVP via the website.
Cost: RVSP for free

West Indian Day Parade
West Indian Day Parade | a katz/Shutterstock

Monday, September 5, 11 am–6 pm
Crown Heights
A NYC tradition dating back to the 1920s, this year, we welcome back the vibrant and West Indian Day Parade with eager appetites. After undergoing a two-year hiatus due to the pandemic, the colorful seven hour-long carnival—which honors the heritage of folks hailing from Trinidad and Tobago, Haiti, Barbados, Jamaica, Guyana, and many more countries—will promenade down its usual route in Crown Heights, starting at Schenectady Avenue and ending at Grand Army Plaza. During the celebrations, nearly 2 million spectators experience lively performances from dancers; shows courtesy of steel-pan and calypso bands; traditional West Indian fare from food vendors; participants flaunting extravagant handmade costumes; and more.
Cost: Free for entry

Interior at Abbode
Interior at Abbode | Photo by Sophie Sahara

Friday, September 9 to Sunday, September 11, 11 am–7 pm
Known for its sublime collection of vintage and one-of-a-kind home decor and lifestyle goodies, the Abbode store in Nolita is teaming up with the collaborative design brand, Infinite, for a limited-time pop-up during New York Fashion Week. Spotlighting women- and BIPOC-owned brands, expect shelves stocked with everything from artwork and candles to vases and jewelry, all sourced from more than 15 small businesses. In addition, if you find yourself in need of event planning or any interior design help, Abbode’s owner Abby Price specializes in those realms as well.
Cost: Free for entry

Feast of San Gennaro
Feast of San Gennaro | Stuart Monk/Shutterstock

Thursday, September 15–Sunday, September 25
Little Italy
In dedication to the patron saint of Naples, the 96th Annual Feast of San Gennaro once again hits the streets of Little Italy, bringing along with it the mouthwatering smells of zeppoles, loads of sausage-and-pepper sandwich stands, and a bevy of themed eating contests. Situated on Mulberry Street between Canal and Houston, the grand procession where a giant statue of San Gennaro makes an appearance alongside speeches by former NASA Astronaut Michael J. Massimino and Mayor Eric Adams will take place on Saturday, September 17 from 2 pm–4 pm. In addition, the festival stage on the corner of Grand and Mott will host live performances every night, but the can’t-miss show is, as always, the 24th Annual Cannoli Eating Contest.
Cost: Free for entry

Cooper Hewitt, Smithsonian Design Museum
Cooper Hewitt, Smithsonian Design Museum | Unwind/Shutterstock

Saturday, September 17
Various locations
As we well know, New York City is home to a slew of illustrious museums that draw crowds from around the world. And this year, on the Smithsonian’s Museum Day, hit up some of our best cultural establishments completely free of charge. Hosted by the Smithsonian Magazine organization, this one-day event encompasses around ten institutions across New York State including spots within the five boroughs like The Jewish Museum; The AKC Museum of the Dog; Cooper Hewitt, Smithsonian Design Museum; and more. From fine art to historical heritage, there’s something for everyone. Find a full list of participating museums via the website.
Cost: Tickets are free online

Webster Hall
Webster Hall | Angelina Pilarinos/Shutterstock

Friday, September 23
East Village
Since debuting on the silver screen in 2001, the movie Shrek has become a cult classic. From the iconic soundtrack (including gems like “All Star” by Smash Mouth) and the unmatched villainy of characters like Lord Farquaad, to inimitable one-liners from the A+ cast of Donkey (voiced by Eddie Murphy), Shrek (Mike Meyers), and Princess Fiona (Cameron Diaz), a die-hard fan base seems to sprout with every new generation and helps maintain the film’s relevancy. So, forget about having to “play it cool” all the time and join the other ogre-lovers at Webster Hall’s Shrek Rave 2. While most details are being kept under wraps, expect DJs playing early 2000s hits off the official album, loads of green face paint, and hours of nonsensical fun.
Cost: Tickets from $54 online, tickets at the door from $35

rolling loud
rolling loud

Friday, September 23 to Sunday, September 25
Squad up with your fellow hip-hop lovers for this year’s Rolling Loud festival hosted at Citi Field. With big name performances by Nicki Minaj, A$AP Rocky, Future, and Playboi Carti, the lineup guarantees a huge crowd. Other heavyweight appearances include Big Sean, Lil Baby, Lil Uzi Vert, Pusha-T, 21 Savage, Saint Jhn, and more. If you’re feeling a bit extra, splurge for VIP access which includes private tables, bottle service, dj sets in between performances, and stage views from an elevated deck. For the full lineup and details on locker rentals, check out the website.
Cost: Three-day general admission tickets from $379

Elsewhere | Photo by Luis Nieto Dickens

Monday, October 31
As far as Brooklyn clubs go, Elsewhere is undoubtedly a year-round staple. Embodying that free-spirited and underground energy of Bushwick, this three-story venue includes multiple stages, several dance floors, a rooftop bar, and an arts space. This year, the lively spot is celebrating its fifth birthday with a wild night of DJ sets (featuring Mura Masa, Riobamba, and Tama Gucci) and, of course, tons of dancing. Seeing that the party falls on Halloween, costumes are highly encouraged and don’t expect to be tucked into bed early that night. Spots are opening up over the next few months, so get your name on that waitlist ASAP.
Cost: Tickets from $103.52

The Manhattan Vintage Clothing Show
Photo courtesy of The Manhattan Vintage Clothing Show

Friday, October 14, and Saturday, October 15
Fill your closet with those impossible to find Y2K threads that have been taking over our social media feeds with a new vintage fit from The Manhattan Vintage Clothing Show. A visit here gives guests access to 70 vintage dealers with their finest threads on display to peruse and snag IRL like olden days. It’s the perfect excuse to old-update your wardrobe and cop accessories that channel the 2000s look we’re all so obsessed about right now. Afterwards, continue your shopping spree with an excursion to the city’s best secondhand thread shops.
Cost: Tickets $15 pre-show online, $20 at door

Saturday, October 22
Randalls Island Park
If a lengthy commitment to training for the 51st New York City Marathon isn’t up your alley, maybe pivoting to an “adventure race” is more your speed. Held on Randalls Island, the New York City Challenge Race features more than 25 urban obstacles over three miles for you to go over, around, and through. All fitness levels are welcome, but be prepared to carry heavy items, scale over walls, slide across cars, and perform other action hero-esque feats.
Cost: Entry starts at $80

Steve Edreff/Shutterstock

Embody spooky vibes via city-wide Halloween festivities

Throughout fall
Various locations
Although we may be too old to trick-or-treat, the city is full of ways to get into a spooky vibe courtesy of cherished October 31st activities. First up, we have another edition of the iconic Village Halloween Parade, which first made its debut back in 1973 and travels up Sixth Avenue in Greenwich Village, beginning at Spring Street and ending at 16th Street. Alternatively, take to the great outdoors in the Glen Oaks neighborhood and get lost in the Queens Farm corn maze. For Manhattan-based al fresco activities, catch a classic creepy flick, like Halloweentown or Halloween (1978), under the stars at the Rooftop Cinema Club. Finally, pull up to Bushwick’s beloved nightclub destination, House of Yes, for the Gala Of The Gone event which features a Halloween evening filled with elaborate costumes, aerialists hanging from above, high energy DJ sets, and more.
Cost: Varies

Roller rink at Rockefeller Center
Roller rink at Rockefeller Center | Rendering by ImageFiction

Through October
It’s official: we’re currently living in a nostalgia era. And thanks to talented influencers like the Berlin-based Oumi Janta or our very own resident Central Park Dance Skaters Association (which has linked up almost every weekend since 1995)—roller skating is also having its moment as one of the hottest trends on TikTok. Now, the can’t-miss spot for this extra special throwback activity is The Rink at Rockefeller Center, which pulls inspiration from original Flipper’s Roller Boogie Palace—an iconic Los Angeles-based rink of the late ‘70s and ‘80s created by Ian “Flipper” Ross. Show off your best moves for the mass of tourists gazing into the sunken plaza or go off and explore the bevy of other roller rink gems spread throughout the boroughs.
Cost: Tickets from $21.85

'A Strange Loop'
'A Strange Loop' | Photo by Marc J. Franklin

Throughout fall
Theater District
After the recent Tony Awards announced its winners in June, we’re more excited than ever to snag tickets for Broadway’s most sought-after shows. Along with the productions that gathered accolades like Six: The Musical and A Strange Loop, plus the recent popular additions like In The Woods, theater-lovers are being blessed with a multitude of new and long-beloved shows. And not to worry, we’ve got all the best tips on how to snag cheap tickets and whether for before an opening number or after the final curtain closes, we’ve got you covered on pre- and post-show eats at the best restaurants in the Theater District and Midtown West.
Cost: Varies

Aunts et Uncles
Aunts et Uncles | Photo by Cole Saladino for Thrillist

Throughout fall
Here in New York City, we own the title for the best pizza and bagels in the world (and we won’t hear it any other way). That being said, these two iconic dishes barely crest the rich culinary breadth that has become synonymous with the Big Apple food scene. While it’s impossible to list them all, we’ve done our best to roundup up a vast range of categories our city excels at including the most iconic old-school eateries, best Chinatown spots, can’t-miss omakase experiences, top tier barbecue joints, essential Black-owned restaurants, sought-after Mexican staples, stellar vegan/vegetarian go-to’s, plus many more you can peruse on our NYC homepage.
Cost: Varies

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Izzy Baskette is a Staff Writer for Thrillist New York. Find her on Instagram.