Autumn in New York, why does it seem so inviting? Billie Holliday said it best—and from the spirited festivals to pumpkin spice oat milk lattes from our not-corporate local coffee shops, it’s all making us feel like we’re home. With in-person events back on the calendar, there are more ways than ever to fall back and embrace this coziest change of seasons. Here are some of our favorites in or just a short distance outside the city.


Take a nostalgic fall foliage train ride (with even more nostalgic pricing).

Those sold-out trips on the 20th Century Limited weren’t the only reason to ride the rails this fall. Keeping with tradition, monthly ticket holders on both Metro North and the Long Island Rail Road can bring friends and family aboard for just $1 every weekend through autumn—the perfect way to escape the city and take in those fall colors.


Sip the apples of your eye at Cider Week New York.

Cider Week New York leads a coordinated effort to showcase New York State’s finest hard cider producers at taprooms across the city—and for the first time, it’s going statewide, with a mix of virtual and IRL events from 10/2-10/17. It’s an adults-only way to enjoy the official fruit of the Empire State, which holds claim as the second-largest apple grower in the entire country (they don’t call this “the Big Apple” for nothing).


Field+Supply, at the Hutton Brickyards in Kingston, has become the “it” event of Hudson Valley fall.

Shop lifestyle wares at Field+Supply.

The modern craft fair, founded by AD100 interior designer Brad Ford, returns to Kingston’s Hutton Brickyards on 10/8-10/10. Considered the “it” event of fall in the Hudson Valley, the curated gathering will draw dozens of the world’s most influential artisans and tastemakers, showcasing designer textiles, ceramics, furnishings, and other goods for home and self.


Go out (east) on the town for East Hampton Village Fall Festival Weekend.

On 10/23-10/24, East Hampton’s Chamber of Commerce has a whole weekend of autumnal exploits planned to remind you how East End life is hardly just a summer fling. Dovetailing the Fall Food & Craft Festival at Herrick Park, there’s an outdoor movie on Saturday, brunch and walking tours on Sunday, and various local business boosters throughout the week.


90s nostalgia illustrations by Chen Reichert at Gowanus Open Studios.

Get your art on at Gowanus Open Studios.

GOS might just be the most exciting self-guided art event in the city—and best of all, it’s back! On the weekend of 10/16-10/17, you’ll once again have the chance to visit some 400 painters, sculptors, object-finders, and other makers who live and/or work in the talked-about Brooklyn neighborhood. You’ll find the canal a little cleaner since the last run in 2019, along with some upgraded waterfront dining at barbecue favorite Pig Beach.


Dust off those lederhosen for OktoberFest NYC.

Munich’s might be cancelled for a second consecutive year, but New York’s is back at Watermark on Pier 15—and extended to make up for the lost time. Admission is free seven days a week through 10/17, with the expected lineup of steins and typical Hofbrau noshes offered a la carte. Other shenanigans: oompah bands, Roller Fräulein, and pretzel floats.


The Great Jack O’Lantern Blaze, a longtime Westchester favorite, now has a second venue on Long Island.

Marvel at the Great Jack O’Lantern Blaze.

Long one of the New York area’s more unique Halloween events, the Blaze features thousands of gourdgeous illuminated sculptures handcrafted from real pumpkins. Artisans assemble some 7,000 of the squash into dinosaurs, a carousel, and countless other installations guaranteed to shame that tea light gaptooth on your stoop. Catch it through late-November at the original Westchester location, at Van Cortlandt Manor in Croton-on-Hudson, or at Old Bethpage Village Restoration on Long Island.


Cozy up at the 41st New York State Sheep & Wool Festival.

Insulation is becoming essential as the calendar progresses, and all the more with a winter ahead that’s expected to be colder—and arrive earlier—than its recent counterparts. Thankfully, this Hudson Valley tradition is back at Dutchess County Fairgrounds in Rhinebeck on 10/17-10/18 for a full in-person experience. Visit the vendors IRL (tickets are single-day only to control crowds), or shop online.


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