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Cuffing season is near, so grab a plus one and get out there.

With the leaves starting to turn and temperatures dropping, it’s the perfect time to get back out there and ready yourself for cuffing season. As the weather crisps up, it brings with it the promise of love…or at least like? Take your permanent plus one out on the town for a night of dancing, to a sky-high immersive art experience, or pack a sweet picnic for the park.

Here’s our list of most fun (and possibly romantic) places to go on a date this fall in NYC.

Throughout fall
FiDi
Overstory at 70 Pine has opened just in time for your next fancy date night. Perched on the 64th floor, the cocktail bar boasts a swanky aesthetic and impressive cocktail list—don’t miss the Gyokuro Martini (vodka, gyokuro green tea, and vermouth). Treat your special someone to a night out on the town by clinking drinks while looking out at the panoramic city views from the wraparound terrace.
Cost: Varies

October 16, noon – 3 pm
Seaport District, Pier 16 and 17
Taste of the Seaport is an ideal place to bring a food-obsessed date (or really anyone who loves to eat). Showcasing the neighborhood’s diversity, community, and culinary prowess for the 11th year, two tickets go a long way with more than 30 of Lower Manhattan’s most notable restaurants such as Brooklyn Chop House, Industry Kitchen, and The Fulton serving up delicious bites; a large variety of wine and beer stations to peruse; and live music performances. After you’ve caught a little buzz, stop by the instructional demonstrations and bond over your mutual inability to properly poach an egg. Also, you can leave knowing you’ve contributed to the future of the community, as all proceeds go to two local public schools. Grab tickets now via the website.
Cost: $50 for general admission

Through to January 2
SoHo
Impress your special someone with a surprise visit to a replication of one of the most renowned artist’s works at Michelangelo’s Sistine Chapel Experience. Within the immersive exhibit, digital projections will display floor-to-ceiling, true-to-size images of the original frescoes painted in the Sistine Chapel. Needless to say, it’s an impressive sight to behold. Carve out an hour and a half of your weekend, and grab tickets via the website.
Cost: $23.10 per ticket

Through October 31
Various locations
Start off the new season with healthy habits and obviously a boozy brunch date. Through to the end of the month, sweat it out at a SoulCycle class and you’ll get a complimentary brunch cocktail code to use after at any of the Union Square Hospitality Group restaurants—like Blue Smoke, Daily Provisions, or Gramercy Tavern. Because nothing quite breaks the ice or solidifies a relationship status more than working out together...right?
Cost: New rider single class prices start at $25

Opens October 21
Midtown
Head up into the clouds for a dreamy date at the soon-to-open SUMMIT One Vanderbilt’s observation deck and immersive experience. Complete with glass elevators that provide unparalleled views of the city, a multi-sensory walk-through art exhibit (Air), sky boxes, and an observation terrace this experience will transport you physically and mentally above the hustle and bustle. Before you head out, visit the inside or outside bar for a cocktail to cap it off. Tickets are available via the website.
Cost: Tickets start at $39

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November 8–14
Various locations
Laugh off the first date jitters at this year’s New York Comedy Festival. Grab a couple tickets to watch headliners like Nick Kroll, Megan Stalter, and Michelle Wolf (with more to be announced closer to the event date). Because there’s nothing better to determine compatibility like discovering a person’s brand of humor… Just remember to bring your vax card!
Cost: Prices vary

Fridays from 5 pm – 11 pm
NoMad
Every Friday, NoMad’s PLANTA Queen is serving $20 platters of vegan dumplings with a heaping side of ‘70s synthesizer disco realness. Pick between the shitake, crispy, potato truffle, or sweet corn for your platter and maybe tack on a small plate from the regular menu (nods to the peking jackfruit and bao sliders). Reservations can be made on Resy.
Cost: $20 per dumpling platter

Throughout fall
Flatiron District
Impress your date with a classic romantic steak dinner moment at the newly opened Hawksmoor. Originally rising to recognition with their flagship restaurant in London, Hawksmoor’s first stateside location now resides in the renovated historic United Charities Building near Gramercy Park. Amid the vaulted ceilings, stained glass windows, and green leather banquettes, indulge in dry-aged steaks and signature cocktails.
Cost: Varies

Throughout October
Various locations
This year’s Oktoberfest is the perfect excuse to spend the day sipping on huge steins of German beer and while simultaneously munching on as many brats and pretzels as you can handle, all the while wearing your finest pair of matching lederhosen. With events happening seven days a week until October 24, there’s plenty of opportunities to snag a couple free RSVPs via the website. If you’re looking for a less literal way to celebrate the holiday season, drop by the newly opened Creamline Beer Garden in Chelsea Market or The Bronx Brewery for a few cold ones.
Cost: Tickets are free, not including beer and food

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Through October 31
Pier 83, Midtown
If you’re not averse to an early morning, there’s no better time to cruise up the Hudson River with Circle Line’s Bear Mountain Cruise. Boarding begins at 8:30 am from Pier 83, where the journey to Bear Mountain begins. While gazing out at the passing autumnal landscapes, Oktoberfest beer, schnitzel, and brats will be available to assuage your appetite. Upon arrival, you and your date can spend a couple hours admiring the natural beauty of Bear Mountain Lake, exploring hiking trails, or checking out the Trailside Zoo, all before you have to meander back to the city. Tickets are available for purchase via the website. Oh, and don’t forget proof of vaccination and a mask.
Cost: $69 for standard seating and $99 for premier seating

Throughout fall
Four Seasons Hotel New York Downtown
The Four Seasons Hotel Downtown’s Picnic in the Park is the epitome of “cute date” vibes. Executive chef Maria Tampakis has put together a luxe picnic basket filled with cheeses, charcuterie, fresh fruit, feta and tomato salads, natural sodas, and baked goodies. Grab a complimentary Biria Bike ride and shoot off to a cozy little spot of your choosing (custom-designed maps are provided as well) to enjoy your haul. Picnics can be booked by emailing concierge.nydowntown@fourseasons.com, just make sure to reach out 24 hours in advance.
Cost: $175 for two people

Throughout fall
Bushwick
Spice up your next date night with a trip to the newly reopened House of Yes. Known for fantastical parties, wildly fun energy, and a beautifully inclusive nature, House of Yes is the spot to be for letting loose and expressing yourself on the dance floor. Think aerialists hanging from above, high energy DJ sets, and themed nights that bring out everyone’s individuality. Pop in on a random night (show up early or you’ll be stuck in line!) or buy tickets for one of the events in advance.
Cost: Varies

Throughout fall
SoHo
Something about the drop in temperature calls for whiskey, and Great Jones Distilling Co. has you covered. Switch up the bar scene and take your next weekend date for a one-hour tour of the first (legal) whiskey distillery since Prohibition. After the tour, snag a seat in the tasting room and try out the wide variety of artisan cocktails (like the Empire State Cobbler—bourbon, apple cider, and nutmeg) and seasonal plates like the slow roasted fall squash.
Cost: $38.50 per ticket

Throughout fall
Various locations
Not to edge into super “basic” territory, but fall and apple picking just go hand in hand. A true breath of fresh air and a quick break from the city can do wonders for your love life. With loads of orchards and farms—like Dr. Davies Farm Stand, Barton Orchards, and Harvest Moon—accessible via bus, car, or train, you and your date will have plenty of options.
Cost: Varies

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