The best fall date ideas in NYC

New York has some of the very best movie theaters, but there’s just something so romantic about watching a movie under the stars. This fall, Rooftop Cinema Club is showing classic horror films including The Shining, The Exorcist, Scream and Rosemary’s Baby on their outdoor screen high above Midtown. Snack on popcorn and your favorite candy while you feel the fall chill run up your spine. (Bonus points if you offer your sweater.)

This fall, the Bronx Zoo is open until 10pm for its first-ever Pumpkin Nights, featuring 5,000 glowing pumpkins, an assortment of local food trucks and plenty of photo ops. The theme is (ahem) “what animals do after dark,” although this event is totally family-friendly. Stroll down the jack-o’–lantern walk, have a bite for dinner and find out if their favorite animal is a red flag. 

OK, we have to ask—has anyone actually read this book? The actual content of Fitzgerald’s novel notwithstanding, the roaring (19)20s and the fabulous, frivolous Jazz Age has been killer party inspo for a hundred years. Transport your date to a world of flappers and Gin Fizzes as you spin them around the dance floor at this immersive experience.  

What could be more romantic than ice skating on the iconic rink at Rockefeller Center under the stars? Holding hands…sipping cocoa…offering your sweater…it’s like a romcom, starring you. The 2023-2024 ice-skating season starts October 21. This fall, they’ll also be opening private Après Skate Chalets, where you can drink a cocktail with your date while gazing out at all the other couples falling in love. 

New York’s newest food hall is an epically renovated historical site offering dosas, tacos, pizza, a raw bar, an Asian grocery and everything else you need to feel like you’re on an epic date, eating and drinking around the world. Jean-Georges’ Vengrochtin’s Tin Building at the South Street Seaport includes two stories of bakeries, bars, restaurants and more to browse and linger in. 

Celebrating a special occasion or anniversary this autumn? A sunset sail aboard the Schooner Adirondack fits the bill for a romantic evening on the water. The gorgeous 80-foot schooner will take you away from the noise of the city, so you can admire all the stunning fall foliage before the sky turns pitch black. You can even bring your own picnic aboard! The bright city lights will welcome you home after a night of conversing and sipping complimentary champagne with your date.

Scoring a coveted seat at a highly anticipated new restaurant is the ultimate New York date move, whether it’s your first offline meeting or a treat for your S.O. Check out some of this fall’s most exciting restaurant openings to reserve a table at an “unusual Italian restaurant,” eat Persian food on Billionaires Row or try kangaroo tartare on Avenue A.

In our humble option, fall’s the best time to take your date on a hike. There’s just something about the crisp air, the changing foliage and the apple cider doughnuts you pack as a romantic surprise to share at the summit. Check out some of our favorite hikes in the New York City area, many of which are easily accessible via train or bus for a day trip.  

Plan a picturesque date enjoying the beautiful autumnal colors on display at one of New York’s prettiest parks. Take a moment to enjoy the great outdoors and peep at all the multicolored leaves in Prospect Park, Central Park and Fort Tryon Park. Want to up the romance factor? Go ahead and pack a picnic for two.

While a trip to Munich may not be in the books, a fall date celebrating Germany’s favorite pastime—drinking beer—is perfect. Check out some of the best Oktoberfest events in New York City for plenty of brews, live music, pretzels, sauerkraut and more Germanic ways to woo your date while day drinking. Prost!

Combat cold autumn nights by warming up next to a brick pizza oven. At Pizza School (pizzaschool.com), you can sign up for a couple’s pizza-making class with your sweetheart. You’ll learn how to master the perfect crust and sauce, including how to properly place toppings, while getting creative (and a little messy). Note: In-person tickets are $325 for couples, and virtual options are available for an at-home date night.

The Great Jack O’Lantern Blaze is one of the best things to do in the fall in the New York area. Admire the beauty of your S.O. in the crisp air with nothing but the romantic glow of over 7,000 jack o’lanterns to light their face. Ogling your “honeybear” and all the pretty gourds isn’t the only draw; you can snuggle up with some hot cider or hot chocolate and take advantage of the stargazing opportunities inside the Pumpkin Planetarium.

No other activity screams, “hold me,” as much as the spooky ghost tours offered in New York during the Halloween season. Take a candlelit stroll through haunted venues such as the Merchant’s House Museum (merchantshouse.org), or explore 'hoods bursting with paranormal activity (i.e. Brooklyn Heights and Astoria) with the folks behind Boroughs of the Dead (boroughsofthedead.com). Your date will be latched onto you so tight, your circulation may suffer—but, like, in a sexy way.

The best way to entertain a date is to make them laugh, right? One of the biggest fall events in Gotham—the New York Comedy Festival—brings some of the best comedians to popular clubs such as the Beacon Theatre and the Apollo Theater. See stand-up legends including Margaret Cho, Nicole Byer and Dave Attell kill it in the spotlight.

Out of all the beer gardens and beer halls in New York, Spritzenhaus offers a romantic ambience, especially during the colder months (the haunt is craftily decorated with white twinkle lights and pine). Rather than plop your keisters at one of the long, wooden picnic tables, opt for more intimate seating by the bar. You and your date can snack on hearty traditional German processions such as pretzels and brats and sip spiked cider, mulled wine or a stein filled to the brim with suds.