October in New York City is by far one of my favorite times of the year. I bring the philosophy behind the word cozy into everything in my life, and that’s the perfect word, to sum up, this time of year. The leaves are starting to change in Central Park, and there’s a sudden crispness to the air that makes you want to cuddle up with a good book. Although this year might look a bit different, there’s still plenty of events to celebrate in October. Read below to plan your next adventure in New York City.
Empire State Building Covid Couples Photoshoot

October 10th ONLY
For the first time, in its 89 years, the Empire State Building will be hosting a couple’s photoshoot for the price of admission to their 86th floor in October in New York City. This opportunity is only available on October 10th between the hours of 11 am and 4 pm, so book soon. Finally, you’ll be able to capture your An Affair To Remember, Gossip Girl, and Sleepless in Seattle fantasies. After purchasing your tickets a link to sign up for a time slot will be emailed.
To book your slot head over to esbo.nyc/cry
Open House New York

October 17th-18th
One of the worst parts of living in the city is that you find yourself doing the same things over and over. If an event comes up you always think, well, there’s always next year, I now know that isn’t necessarily true. This is one of those events that I’m kicking myself for not going to. Advertised as a citywide celebration of architecture, this is a look into some of the most beautiful, historic, modern, residential, and industrial buildings this city has to offer. Although it’s still going to happen, it will look a bit different, events won’t be listed until October 12th. Open House New York tickets are $150 and completely tax-deductible as a charitable donation.
Seaport Rooftop
Currently listed until October 16th
This charming green space may be one of the best things you do this October in New York City. I’m going to be completely honest though and say all tickets are sold out for Seaport Cinema. BUT you can still join a waitlist, and they may always add on more showtimes depending on the weather.
You can also book a mini lawn for drinks on weekdays, 7-days a week, until October 16th. No external food and drink are permitted, but each space offers a menu of items, an umbrella, cabana chairs, a USB charging port, and a Yeti Cooler for purchased drinks. Each lawn can fit up to 8 guests and can be reserved for a $1.59 donation to Bowery Mission. Grab your pals and enjoy the remaining days of outdoor cocktails!
For a calendar events https://thegreens.pier17ny.com/calendar
Magnolia Bakery Pumpkin Gingersnap Banana Pudding

The banana pudding at Magnolia Bakery is honestly legendary. It’s the #1 item I would recommend from the menu, so I’m always excited to try a new variation on a favorite. The mix of the pumpkin with the gingersnap is the perfect blend of some of the best fall flavors. I swear on October 2nd I was lined up around the block of Magnolia Bakery on the upper west side just waiting to get my sugar fix. For all those confectionery fans of this historic brand that don’t live in NYC, you’re in luck! Magnolia Bakery now ships nationwide.
Open Air Dinner and a movie
Month of October
An open-air dinner and a movie is just the ticket for date night in the time of Coronavirus. Better yet, this is hosted at the modern and picturesque setting of The William Vale, one of the most fascinating buildings in Williamsburg. Hurry and purchase tickets because these events often get sold out quickly. All tickets include popcorn and dinner which you can select after purchasing your ticket.
Purchase tickets here
The Village Halloween Parade

October 31st
Technically, this Halloween parade was canceled, but they’re still teasing an event. Although they won’t disclose any details surrounding the event or “trick that will be a treat,” stay tuned for more to come. The hosts felt very strongly that the event must not take place online, so a COVID-19 safe surprise will be announced. They will still be sticking with tradition in one way, Master Puppeteer Basil Twist will have a giant spider come out of the Tower of the Jefferson Market Library on Halloween night.
For more updates check out their website here
Century 21 Store Closing Sale

Currently set to close at the end of November
I feel a bit guilty saying that I’m excited about a store closing but a deep discount is pretty exciting, especially right before the holidays. The famous New York discount chain, which was founded in 1961, is currently set to close its doors at the end of November.
Of course, as most common for mid-westerners, I learned about this New York Institution from Sex and The City when Carrie Bradshaw stated, “Century 21, the discount shop downtown was the best part of jury duty.” Make sure to send this icon off with a bang. There’s a lot of debate on which one is the best, but the flagship is at 22 Cortlandt Street down in Wall Street.
Private Bubble Dining at Cafe du Soleil
Currently listed until the end of November
Maybe it’s the feeling of sitting in what feels like individual greenhouses, maybe it’s the privacy in such a public space, or maybe it’s just enjoying not freezing your butt off, whatever it is, take a minute to book a reservation at Cafe du Soleil. With inflatable igloos lining the streets until it gets too cold you can enjoy the luxury of coronavirus dining while still feeling safe. This French bistro is truly delicious. I ate here not too long ago on a whim when a friend suggested it, and I could not have been more pleased with the menu.
To book your next reservation click here!
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