By: Stefanie DiMartino

Fall is officially here! The air is cooler, and the days are getting shorter, but that doesn’t mean there’s a shortage of things to do! October is one of the best months in NYC and I’m sharing the best things to do and see, the best in dining/drinks, and the best entertainment and art/exhibits. These are my top NYC picks for this October!

The Top 16 Best Things to do in NYC this October 

For more on the best things to do in NYC in autumn/winter, watch my guide below: 

THINGS TO DO/SEE + PARTIES

THE NEW YORK COFFEE FESTIVAL

Friday-Sunday, October 6-8 | $45+

Metropolitan Pavilion, 125 West 18th Street, New York, NY 10011

Attention all coffee lovers and aficionados! This festival is for you! If you run on coffee, then you must check out the New York Coffee Festival!

“The festival will feature live experiences from over 100 coffee, food and equipment suppliers. Visitors will enjoy endless free coffee tastings, interactive workshops, demonstrations from world-class baristas, delicious street food, intoxicating coffee cocktails, live music, art and so much more.” – The New York Coffee Festival

NYC OFF-BROADWAY WEEK

Now – October 15 | 2-for-1 tickets! 

NYC Off-Broadway Week℠ is back now through October 15th. Enjoy amazing performances and be entertained in NYC’s most intimate theaters! See unique shows such as Drunk Shakespeare, Blue Man Group, Alice in Wonderland The Musical, Titanique, and more!

Use code OBW23 to book your 2-for-1 tickets!

HYPNOTIQUE

Last Chance! Ending October 21st | Fridays & Saturdays, 10:30pm | $65+ | Age 21+

The Club Car at The McKittrick Hotel, 530 West 27th Street, New York, NY 10001

“The all-new Hypnotique revue offers a unique after-dark experience that envelops you. Audiences are captivated by spontaneous performances and mesmerizing dancers, accompanied by daring sonic soundscapes in a surreal ambiance in The Club Car. During the performance, a highly-skilled ensemble cast showcases breathtaking live acts amongst the audience, enticing them on a hypnotic journey that delves into the deepest fantasies of the mysterious feminine allure. Cocktails inspired by the experience, including the signature Hypnotonique (an electrifying punch made with cucumber-infused vodka, elderflower liqueur, and grapefruit juice), are available from The Club Car’s bar.” – The McKittrick Hotel/Hypnotique

No night out at The McKittrick is complete without dining at Gallow Green, the most enchanting rooftop bar and restaurant in NYC! Check it out and enjoy a delicious meal before the performance! 

FALL FEST

October 7-8, October 14-15, & October 21-22 | 10am-6pm | $5-7+

Weed Orchards & Winery, 43 Mount Zion Road, Marlboro, NY 12542

To celebrate everything fall this month, head up north for Fall Fest! Weed Orchards & Winery is located in Ulster County, New York which is approximately 60 miles North of NYC. You can enjoy the panoramic views and beautiful autumn colors while picking your own produce! Some of the Fall Fest highlights include pumpkin picking, pumpkin carving, a playground, face painting, hayrides, and live music! It’s fun for the whole family! They will also be serving fall themed food and drinks-seasonal beers and sangria, and delicious Jane’s ice cream. Don’t forget to get your apple cider donuts and caramel apples!

APPLE + PUMPKIN PICKING

With autumn finally here and the cooler weather upon us, there is no better fall/October activity than to go apple and pumpkin picking. Certainly, apple and pumpkin picking is the perfect way to get into the autumn spirit. There are so many great farms and orchards to choose from that are all relatively close to NYC. You can read more here about my Top 7 Best Apple and Pumpkin Picking Farms. 

PIZZA WINE MOVIE NIGHTS

Select nights in October | Happy Hour starts at 6pm | $35+

Rooftop Reds, The Brooklyn Navy Yard, 299 Sands Street, Bldg 275, Brooklyn, NY 11205

For a different kind of fall experience, visit Rooftop Reds, NYC’s only rooftop vineyard. For October, you can watch spooky and scary movies to get in the Halloween mood such as Get Out, Us, Night of the Living Dead, The Crow, Hocus Pocus, The Ring, and Bram Stroker’s Dracula all while eating pizza, drinking wine, and taking in skyline views.

CLASSIC HARBOR LINE: FALL FOLIAGE CRUISE

Fridays, Saturdays & Sundays | October 13 – early-mid November | $108+

Certainly, one of the most scenic ways to enjoy autumn and the changing leaves is from the water! Classic Harbor Line has 6 different fall foliage cruises to choose from, and you can’t go wrong with any of them! 

“Celebrate Autumn on one of our NYC Fall Foliage Cruises.  Join us for the last leaves of fall and jump aboard one of our classic boats and head north up the Hudson River to take in the beautiful fall foliage. Escape from the chaos of the city and join us for a 2.25 – 2.5 hour fall foliage cruise on luxury yacht Manhattan or hop aboard a 3.5 hour fall foliage sail aboard Schooner Adirondack! Feel the crisp autumn air upon your face and take in the brilliant crimson red, pumpkin orange and a golden yellow of the Hudson Valley for an afternoon of leaf-peeping.” – Classic Harbor Line

OPEN HOUSE NEW YORK

Friday-Sunday, October 20-22 | Various NYC locations | FREE!

“Open House New York is an annual festival that opens hundreds of noteworthy or significant places across the five boroughs to foster discovery and delight for all New Yorkers and deepen the public’s understanding of how design can strengthen communities and improve quality of life. 

The 21st Annual OHNY Weekend festival will offer a mix of in-person experiences, self-guided explorations, and digital content—inviting you to glimpse everything from single rooms, studios, factories, and public spaces to entire buildings, blocks, bike corridors, and waterways.” – OHNY 

DAYBREAKER NYC: TOGETHER TOUR

Saturday, October 28 | 5pm-8pm | $52+

The Green-Wood Cemetery, 500 25th Street, Brooklyn, NY 11232

“Welcome to the finale of our 10-Year Anniversary Together Tour. We chose the theme “Togetherness” to shine a light on the importance of belonging, friendship, and real social connections to support a meaningful life — and to heal the world. We promise to deliver memories to bond us and music to heal us. All you have to do is wake up & show up — for yourself and each other.” – Daybreaker

Note: No costumes or face paint are permitted in Cemetery out of respect for those who are buried there. Anyone with costumes or face paint will be denied entry.

PIER 17 PUMPKIN ARCH

Now – November 7 | Open 24/7 | FREE!

Heineken Riverdeck at Pier 17, 89 South Street, New York NY 10038

For the most perfect and instagram-worthy fall/Halloween photos, you must check out the Pier 17 Pumpkin Arch. 

“Pumpkins. Fall foliage. The Brooklyn Bridge. Fall is here and we’re reimagining our annual Pumpkin Arch. The Pumpkin photo installation has reappeared at Pier 17 for a limited time. Stroll down Fulton Street to Pier 17 to discover a bountiful seasonal frame to elevate your Halloween photos. The idyllic backdrop seals this as a not-to-be-missed New York moment.” – Pier 17

FUNKY EXPERIENCES

Fridays, Saturdays, & Sundays, Custom day + time | Starting at $49+

I love New York City so much that I started a tourism company here. We offer a variety of tours around the city, from history, to sightseeing, to shopping, and one of my favorites – our food tour! 

Rated 5-stars on TripAdvisor and the winner of the “best of the best” award in NYC, you definitely do not want to miss out on any of these amazing tours! There are different tour options available to choose from to fit your interests AND your budget! For a truly unique experience, book a custom-designed private tour with our expert NYC guides!

Newest to our tour lineup is the Must-See Manhattan tour! This experience shows you Manhattan’s most iconic sites during a 2-hour walking tour. And, you can add on Top of the Rock tickets to end your experience with breathtaking views of the city’s skyline on a historic skyscraper! 

Visit and learn the unique history of iconic sites such as Times Square, Grand Central, the NY Public Library, Fifth Avenue, Rockefeller Center, Radio City Music Hall, St. Patrick’s Cathedral, and more! Plus, we’ll take you inside Grand Central for an exclusive tour of its secrets.

For the best of both worlds, with food and sightseeing, consider joining the Best of New York Food Tour offered on Sunday mornings. The tour includes five dishes at delicious restaurants and a historic walking tour through Brooklyn!

Planning a vacation to NYC? If you’re feeling overwhelmed and don’t know where to begin, we are here to help! With Funky Tours Concierge, our team of experts can help you plan your dream NYC vacation! You can make your NYC trip and experience more special with custom-designed plans that fit your budget and your unique interests.

AND SPECIAL FOR OCTOBER – HALLOWEEN GHOST TOUR!

Friday & Saturday, October 13-14, October 20-21, & October 27-28 | 6:15pm | $55+

Get into the spooky season spirit and join us (if you dare) for a spine-tingling ghost tour through Manhattan’s Greenwich Village, beginning at New York’s oldest haunted bar and leading you to a mass burial ground with 20,000 souls. Along the way, you’ll hear bone-chilling ghost stories, explore infamous sites, and have the chance to encounter the ghost of Aaron Burr in an old carriage house, creating an unforgettable and haunting experience.

DINING + DRINKS

NEW YORK CITY WINE & FOOD FESTIVAL

Thursday-Sunday, October 12-15 | Various times | $95-$400+

Calling all foodies! “The Food Network New York City Wine & Food Festival presented by Capital One (NYCWFF) is NYC’s premier wine and food festival. The four-day annual Festival showcases the talents of the world’s most renowned wine and spirits producers, chefs, culinary personalities and America’s most beloved television chefs while supporting New York City metropolitan area’s only provider of life-sustaining meals and nutrition counseling for New Yorkers living with severe illness, God’s Love We Deliver.” – NYCWFF

LORELEY BEER GARDEN: PUMPKIN KEG SEASON

Now – November 5, 2023

If you want to celebrate everything fall and pumpkins, visit Loreley Beer Garden! Pumpkin Kegs Tapped & Filled with Southern Tier Pumking Beer, Pumpkin Spice Cocktails, Pumpkin Spice Cold Brew Cocktails, Southern Tier Pumking Craft Beer, Hot Bourbon Cider & German Glühwein, Seasonal Craft Ciders & Cider Cocktails, Rotating Oktoberfest Craft Beer List & Oktoberfest Specials & more!

And, from October 18th-31st, you can enjoy Loreley’s Haunted Beer Garden!

CHAMPAGNE BRUNCH

Gallow Green, 542 West 27th Street, New York, NY 10001

Ending Soon! Saturdays & Sundays until October 22 | 10am-2pm | $70+

What’s the weekend without brunch? Gallow Green is the dreamiest garden rooftop in NYC, and you can wine and dine at their Champagne Brunch only until Sunday, October 22nd. It’s the perfect fall escape with delicious drinks and food!

SERRA BY BIRRERIA

Eataly NYC Flatiron, 200 5th Avenue, New York, NY 10010

Once again, SERRA by Birreria has been transformed into a festive fall oasis! The iconic rooftop restaurant features rustic dishes, vibrant handcrafted cocktails, an immersive floral look, and more. Meaning “greenhouse” in Italian, SERRA always changes with the seasons, offering a unique dining experience reflective of the Italian countryside.

BROADWAY SHOWS

THE COTTAGE

Ending soon! Final Performance October 29 | $55+

“Broadway’s side-splitting romp is an outrageous tale of sex, betrayal, and desire as one woman decides to expose her latest affair to both her husband — and to her lover’s wife. The true meaning of fate and faith, identity and infidelity, love and marriage are all called into question as a surprising and hilarious web of secrets unravels in this ridiculously funny romantic comedy.” – The Cottage

For even more autumn fun, read here! 

In conclusion, these are the top 16 best things to do in NYC this October. Have fun and stay safe!