The Best NYC Date Ideas to Spark Romance This Fall

Whale watching, tandem bike rides in Central Park, food festivals, and more.

With the carefree days of summer now officially behind us, next on our priority list: staying as warm and cozy as possible throughout the crisper season.

Along with rib-sticking meals from exciting fall restaurant openings (expect projects from industry heavyweights behind favs like Carbone, Dame, Dhamaka, and Raoul’s), it’s also the ideal time of year to swipe right to dating, because chunky sweaters alone won’t keep us snuggled up at night.

For autumn, we’ve rounded up plenty of ways for you and your special someone to embrace the romance of fall in full force. From whale watching and tandem bike rides to food festivals and spooky pop-ups, here are the best places to go on a date in the upcoming months.

Event Cruises NYC
Event Cruises NYC

Saturday, September 10 to Sunday, October 30
Pier 36, Lower East Side
One of the many benefits to living in New York City is our proximity to sparkling rivers. Embark on the East River with your plus one on Event Cruises’s Whale Watching NYC Adventure Cruise. The ship takes off every weekend, and boarding begins 30 minutes before departure from Pier 36. Voyagers may spot species such as humpbacks, minkes, and more, while sipping on specialty cocktails and hot cocoa. Prepare to encounter a myriad of whales flipping and flopping and don’t forget your binoculars!
Cost: $85 a ticket

Paragon
Photo courtesy of Paragon

Throughout fall
Bed-Stuy
As chilly weather falls upon us and we bid adieu to backyard parties, it’s time to get back inside. Relatively new multi-storey discotheque Paragon has popped up just in time to carry us into the changing season, with lineups of notable DJs like Tory Stiletto and Khadija. Backed by John Barclay, who previously operated multiple Brooklyn nightlife spaces like Bossa Nova Civic Club and 285 Kent, the club has earned a reputation for its inclusive environment and glamorous interior. It’s also the perfect place to dance with abandon and show off your Y2K fits as you bring out your date’s wild side. Make sure to purchase tickets in advance.
Cost: Varies

Black Lagoon
Hellraiser cocktail | Photo courtesy of Black Lagoon

Saturday, October 1 to Monday, October 31
East Williamsburg
Starting in October, industrial-chic live venue Our Wicked Lady will transform into a horror-filled pop-up bar called Black Lagoon, adorned with decor inspired by goth culture and cult horror—think life-sized caskets, dungeon vibes, and more. The experience will feature aptly-named cocktails such as Lilith’s Cup (rum, passionfruit syrup, glitter) and Hellraiser (tequila, rum, orange liqueur, spiced oat orgeat), served in skull-shaped glassware. Grab a drink and rock along in your best costume (which is optional) to punk and metal while embracing your inner goth.
Cost: Free to enter

Starting Friday, October 7
Midtown
Wonderland Dreams is a 26,000-square-foot immersive art exhibit loosely inspired by Alice’s Adventures in Wonderland. The dreamy oasis is hand-painted by Alexa Meade (who also painted Ariana Grande for her “God is a woman” video) and features rose gardens, multi-colored mushrooms, and giant playing cards. Once inside, cosplay iconic characters like the Queen of Hearts and the Mad Hatter before heading to the Painted Wine Bar and Café for color-changing beverages in custom-made bottles and glasses, as well as oversized cookies, and tiny cupcakes. Take note: the bar is also open to the public by reservation (which will be available soon) or walk-ins.
Cost: Starting at $46 a ticket

New York City Wine & Food Festival
Photo courtesy of New York City Wine & Food Festival

Thursday, October 13 to Saturday, October 15
Various locations
Instead of being confined to a table all night, swap out the small talk for the city’s premiere food extravaganza: the New York City Wine & Food Festival. Celebrating its 15th anniversary, this year’s top talent includes chefs like Yotam Ottolenghi, Daniel Boulud, and Sohla El-Waylly, along with over 80 events consisting of tastings, seminars, intimate dinners, and more. Gallivant around the various happenings in locations throughout the boroughs and indulge in everything from aperitivos to Mediterranean bites. In addition to interactive lessons like a Cocktail Making Master Class with the Caribbean eatery, Kokomo; annual highlights include the Grand Tasting and popular festivities like Burger Bash and Backyard BBQ. Purchase tickets for individual events or splurge on one of the festival’s packages.
Cost: Individual events start at $115, packages start at $312

Love Apple Farm
Love Apple Farm

Throughout fall
Various locations
The madness of city life often forces us to keep our guards up—but to reveal a more vulnerable and softer side, escape the five boroughs to sip fresh apple cider and peep gorgeous fall foliage with your boo. A bevy of nearby orchards and farms in Hudson Valley and beyond offer acres of apples waiting to be picked, and whether you opt to stay closer to home and indulge in fresh doughnuts at Wilkens Fruit & Fir Farm in Yorktown Heights or hang with some animals at Love Apple Farm’s petting zoo in Ghent, there are plenty of destinations that’ll help unveil your inner cheeseball.
Cost: Varies

Smith & Wollensky
Photo courtesy of Smith & Wollensky

Throughout fall
Midtown
If you’re looking to go back to basics, we don’t blame you; sometimes all a date needs is delicious food, ambient lighting, and a good atmosphere. And at Smith & Wollensky, even after more than 45 years, the iconic steakhouse has still got it—and continues to dish out excellence within its legendary dining room. This fall, wine and dine your plus one though the special three-course Weekend Wine Dinner. At $95, dig into appetizers like Fresh Shucked Oysters or Line-Caught Tuna Tartare and mains like Cajun Rib Steak, 26-oz Prime Rib, or filet mignon four ways, all accompanied by a selection of wines including Pasqua Prosecco and Smith & Wollensky Sauvignon Blanc. Just make sure to save room for their Famous Carrot Cake.
Cost: $95 per person

Throughout fall
Central Park
Whether you want a leisurely ride or to embark on an in-depth tour of Central Park, Bike Rental Central Park offers bike, e-scooter, and e-bike rentals as well as free helmets, locks, and maps to cycle around sights like the Conservatory Garden, Bethesda Fountain, and more. And if you’re feeling particularly intimate, opt for a tandem bike and gaze at the changing leaves with your loved one. You can also take bike tours through Wheel Fun Rentals, which offers bike rentals as well as map guides featuring famous landmarks for both Prospect Park in Brooklyn and Flushing Meadows Corona Park in Queens.
Cost: Starting at $19

Photo by Mark Weinberg, courtesy of Levain Bakery

Throughout fall
Various locations
Must-try old-school restaurants in New York City are abundant, but when it comes to cookies, the sole institution remains Levain Bakery. Their iconic Chocolate Chip Walnut cookie helped put them on the map, but what keeps us returning are new seasonal treats like the Fall Chocolate Chunk, debuting on September 14. The cookie features an array of autumnal spices like ginger, nutmeg, and cinnamon, layered with melty Valrhona chocolate. Or to satiate other cravings, choose from a plethora of delectable pastries like the Sour Cream Coffee Cake, Oatmeal Raisin Scone, and Lemon Slice; along with savory items like Ciabatta or Whole Grain Loaf.
Cost: Varies

Throughout fall
Williamsburg
If you’re already dreading the onslaught of fall flavors headed your way (looking at you, Starbucks), switch things up and take your date to Juice Haus, the brand new juice bar at Padel Haus, NYC’S first and only padel club. Juice Haus offers juices such as the Immuno Shield juice (kale, spinach, wheatgrass, spirulina, lime, apple) and smoothies like Popeye’s Fave smoothie (spinach, banana, peanut butter, protein). You’ll want to hang around for a bit, given the space (designed by interior designer Bianca Chevallard) is decked out with greenery, plush couches, and modern touches.
Cost: Varies

ENLY
Photo courtesy of ENLY

Throughout fall
Nolita
Sometimes, there’s nothing more classic than a coffee date. And at Nolita hotspot ENLY, not only can you spark a conversation over espresso, matcha, herbal teas from Devoción, and specialty offerings like their comforting Lavender Oat Milk Latte, but the coffee bar and shop also specializes in hand-poured candles made with coconut wax and soy. Within a modern space offering a calming solace that’s bound to do wonders for any first-date jitters, take in the luxurious fragrance wafting through the air—and look out for after-hours candle making classes expected in the future.
Cost: Free to enter

Swingers
Photo courtesy of Swingers

Throughout fall
NoMad
Swingers is a newly opened golf club in the heart of Manhattan featuring three nine-hole golf courses, gourmet street food, six cocktail bars, and plenty of seating. Head over to the lavish, London-famous golf experience, where the course features a pastoral landscape rife with flower beds and swinging pendulums. The venue offers three separate nine-hole courses varying in difficulty, featuring plenty of fun obstacles. After working up a sweat, head over to the clubhouse to indulge in grub from Sauce Pizzeria, Miznon, Fonda, and Mah Ze Dahr Bakery, as well as adult beverages like the Manhattan Swing (bourbon, vermouth) and Slippery Slope (cognac, rye whiskey).
Cost: Starting at $26 a ticket

Chamber Magic at Lotte New York Palace
Chamber Magic | Photo courtesy of Lotte New York Palace

Make your date spellbound with a reopened classic restaurant and nearby magic show

Throughout fall
Midtown
Not only is Michelin-recognized The Lambs Club—an old-school style haunt known for its classic ambience—back, but it’s now under the wing of esteemed chef Michael White (Fiamma Osteria, Altamarea Group). Along with breakfast, lunch, and dinner, the reimagined restaurant offers a pre theatre menu featuring classic cocktails as well as dishes such as Crab Salad, Salmon, and Strawberry Cake. Once you’re officially satiated, take a quick stroll over to Lotte New York Palace for an enchanting experience with the world-renowned magician Steve Cohen at his show Chamber Magic. The experience features mind-reading, conjuring, and sleight of hand in the Palace’s elegant Madison Room.
Cost:General admission starts at $125

Photo by Ashley Sears, courtesy of Pine & Polk

Keep it cheesy with a DIY charcuterie board

Throughout fall
Various locations
The beloved neighborhood butcher Dickson’s Farmstand Meats offers a tasting bar concept called The Salumi Bar on the lower level of Chelsea Market. The interactive experience boasts a build-your-own charcuterie board, featuring cheese from Saxelby Cheesemongers, house-made cold cuts, and other snacks alongside a wine list and craft beers. Or for a more clandestine spot, hidden behind a wall of chocolates at Pine & Polk provisions shop in SoHo, Manhattan speakeasy PS offers a DIY workshop called That Cheese Class” hosted by cookbook author Marissa Mullen. Along with an assortment of local and artisanal cheeses, meats, produce, and wine, Mullen will also share food photography tips.
Cost: Varies

Throughout fall
Pier 83, Midtown
It may seem odd to propose a nighttime cruise just as the weather starts to cool down, but don’t worry, we’re one step ahead of you. Circle Line’s Harbor Lights Cruise offers a temperature-controlled deck and indoor cabins perfect for a sail down the Hudson River. The ship takes off at 7 pm from Pier 83, and voyagers can expect to gaze out at stunning landmarks like the Statue of Liberty and Chelsea Piers, while enjoying wine, cocktails, and snacks with sparkling skyline views.
Cost:Tickets start at $35 for standard seating and $60 for premier seating

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Kelsey Allen is an editorial assistant at Thrillist.