Joke all you want about how the seasons seem to blend together in New York City -- we’re still lucky enough to have them, and each one is romantic in its own way. But fall’s got it all: apple picking, pumpkin patching, cozy sweaters, cider, stunning foliage, novelty lattes, and sexy Halloween costumes.
Citywide Oktoberfest actually starts in September, but you can still catch up! Swing by Munich on the East River for German brews and bites by East Village restaurant Zum Schneider, or take a bite out of a giant pretzel at Oktoberfest NYC at Pier 15. And remember: Oktoberfest is a moveable feast. You can celebrate anywhere beer is sold.
NY, NJ, and CT Once your mandatory seasonal applepicking is out of the way, start a new couples cliche: Pumpkin patching! It’s just as colorful for social media, you can still turn the fruits of your labor into sweet treats, and you can get extra mileage out of the adventure by planning to carve that baby onto a Jack-o’-lantern on your next date. Consult our list of NYC-area pumpkin patches and get pickin’!
Upper West Side Skip the popcorn garbage at your local sticky-floored multiplex and head to Lincoln Center, where they usually host fancy stuff like the opera. Sure, you’ll pay a bit more at the New York Film Festival than you would for a normal flick -- most tickets are $25 for non-members -- but from September 27-October 13 you can see documentary debuts, revivals not seen on the big screen for years, and have the chance to hear from industry insiders.
Share a raging inferno of a cocktail
Citywide When that crisp autumn air creeps in, warm up with a flaming libation. We’re partial to the Volcano Blast at Otto’s Shrunken Head -- a super-strong rum-based tiki concoction set ablaze. The $35 cocktail is more than enough for two, and the bar’s island vibes will remind you of the real thing.
Citywide The wind in your hair, sweeping skyline views, booze -- rooftop bars are made for romance. Take your pick from a plethora rooftop spots that are still fit for fall, and settle in around sunset for golden hour amber hues. Sure, you’ll pay a little more for a cocktail than you would on land, but the ‘grams will surely make your ex jealous.
Go camping, sort of, in the middle of Brooklyn
Cobble Hill Dirt in your hair. Bugs in your sleeping bag. Wolves circling, baring their glistening fangs as you huddle with your honey on the roof of your car. Who needs it! Instead, Go faux-glamping at Camp, a hunting lodge-themed bar in Brooklyn. Between rounds of Big Buck Hunter and cheap beers, you can roast s’mores over a mini-fire at your table and revel in the great indoors.
Citywide Climes have got to be just right to truly enjoy our city’s outdoor food festivals. Too cold and eating outside is uncomfortable; too hot and it’s downright punishment. Take advantage of milder fall days at LIC Flea & Food in Queens and Smorgasburg in Brooklyn while you can.
Flex at trivia
Citywide Everybody loves a know-it-all, and NYC has a themed trivia night for all “well, actually” types. Have you seen every episode of The Simpsons at least twice and have sonorous opinions on its golden era? Head to The Gutter. Would your pop culture proficiency put Siri to shame? Shuffle over to Metropolitan. Are you just a general genius? Check out The Wolfhound.
Citywide You could quietly change your relationship status on social, or you could introduce your new flame to your rando old high school friends, rando influencer followers, and rando whoever’s still on Snapchat with a colorful splash. Set a date for a “candid” photo shoot at pop-ups like the ball pit at Color Factory, or, if you think this love is built to last, the permanent Decorative Arts and Period Rooms installation at the Brooklyn Museum.
Citywide Although we’re better known for our $18 cocktails, NYC still has a smattering of BYOB restaurants where you can expand your beverage selection beyond the typical merlot/cab/mystery blend menu offerings. Pick a spot from our roundup of the best BYOB spots in town, set a price point, and compete to see who can bring the better bottle. Loser picks up the (slightly less expensive because you avoided the booze markup) tab.
Learn a few new positions...
Garment District ... yoga positions, that is. Stretch, bend, and soar into partner poses during a session (or a week of sessions) of AcroYoga at the Om Factory. Single classes start at $15.
Talk about sex, baby
Flatiron Museums can be subtly sexy, with their tasteful nudes and needlessly sensual depictions of fruit. There’s nothing subtle about the Museum of Sex, where current exhibitions include a bouncy castle fashioned after breasts.
TBA location Sofar Sounds shows pop up in intimate, undisclosed locations -- someone’s apartment; the back of a retail shop; a gallery space. You’ll apply for tickets online through a lottery and receive notification 24 hours in advance if you’ve won access to a performance. Prepare to sit cross-legged on the floor and BYOB. Even if you end up with a musical dud, your date will be impressed with your insider knowledge.
Have a boozy brunch
Citywide If you’re fast enough, each drink can be as cheap as a bodega umbrella. Good on you if this is technically the conclusion of yesterday’s date.
Visit a monastery-turned-medieval art museum
Washington Heights Visiting the Cloisters is as close as you’ll ever get to being a Game of Thrones character. The Metropolitan Museum of Art’s outdoor outpost will transport you and your dragon queen or king to a medieval wonderland reminiscent of Westeros -- hopefully sans bloodshed. Suggested admission is $25.
Take a turn on Brooklyn's finest carousel
Dumbo After brunch and day drinks in Dumbo -- Juliana’s for pizza and Gran Electrica for margaritas -- pop over to Brooklyn Bridge Park and hop on the beautifully restored Jane’s Carousel. The painted ponies will bring some whimsy to your social media posts. Tickets are $2.
The Bronx The 250-acre National Historic Landmark is open for business year-round, and the place is especially peaceful during the fall. Check out the spooky pumpkin garden, the seasonal walk, the holiday train show at the season’s end, or just wander the grounds unbound. New York City residents can get in for as little as $15.
Gallery hop on the West Side
Chelsea Take your muse on a self-guided gallery tour. Most Chelsea art joints open their doors to the public on Thursdays, and some even serve free wine. Spend all that pre-gaming money you saved at one of the neighborhood’s best restaurants.
Play shuffleboard on the banks of the canal
Gowanus, Brooklyn OK, the palm trees are plastic. The flamingos are fake. And the canal is toxic. But the resort vibes at the Royal Palms are the real deal. Make this your dating destination for when you want outside feels after the weather stops cooperating.
Enjoy an island getaway
Departing from lower Manhattan Break out your compass app and board the Staten Island Ferry to New York City’s westernmost borough. The free ride boasts beautiful views of the skyline and a cash bar that, while modest, gets the job done. Once you’re back on land, take a short walk to SI’s own Flagship Brewery, where you can make-believe it’s still al fresco drinking season at indoor picnic tables.
Citywide Now that dancing is finally (sort of) legal in (some) NYC bars, grab your partner and shimmy, shake, cha-cha, or merengue at some of our favorite dance spots.
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