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Apples, Pumpkins & Headless Horsemen: Here’s Why You’ll Fall for These Autumn Activities in Upstate New York

Fall foliage at Breakneck Ridge, a hiking trail only an hour and a half from Manhattan.
Gilad Gamliel
Written by Gilad Gamliel

New York is famous for many things — the Empire State Building, foldable thin crust pizza, and no-nonsense pedestrians who pay no mind to oncoming taxis but pay every mind to oncoming pigeons. With the grandeur and allure of the city, it’s easy to forget that the state of New York extends far beyond the five boroughs, and that the region undergoes a dramatic transformation during the fall season.

Those of us born and raised in New York are well-versed in this —  New Yorkers from Long Island to the Bronx flock up into the Hudson Valley every October for the all-too-exciting leaf-peeping season, sipping on hot cider and munching on cider donuts. The fact is that autumn in New York is underratedly one of the best times to visit, and to do so, you need to grab a train from Grand Central to hitch a ride upstate. The trip is worth it, however, for a chance to experience some of these upstate New York fall activities you’ll absolutely fall in love with.

Pumpkin and Apple Picking

Upstate New York Fall Activities - Apples at the Orchards of Conklin in Upstate New York

Apples at the Orchards of Conklin in Upstate New York

Fall is harvest season, and true New Yorkers know that can only mean one thing: heading upstate to pick some apples. Beginning in September and lasting through mid-October, apple-picking season opens up all these delightfully quaint farm stands and orchards along the edges of the Hudson Valley highways — the sort that make you feel like you’ve gone back in time. You can drive anywhere from 30 minutes to 4 hours north of the city and find no shortage of apple orchards that feature all types of apples. Red Delicious, Granny Smith, Gala, Honeycrisp — you name it, they have it. But be sure to get there right smack in the middle of the season around mid-October to snag the most types of apples, as they can disappear quickly.

Upstate New York Fall Activities - The author and a friend relaxing on an apple tree at Outhouse Orchards.

Me and a friend relaxing on an apple tree at Outhouse Orchards.

Almost as synonymous with fall as apple picking, is pumpkin picking. With a season that lasts much longer into fall (you can pick pumpkins well into November), pumpkin picking is a family-friendly hit that can turn a half-day activity into a whole day excursion. Grab the biggest one you can find from any apple orchard and bring it home to carve with the kids or even with some friends over a glass of wine. Luckily, most apple orchards turn their operation into a full-fledged autumn wonderland, so you should have no trouble finding pumpkins anywhere along your Hudson Valley apple route.

My personal favorite spots for apple and pumpkin picking are Outhouse Orchards and Orchards of Conklin, both just an hour north of the city. I’ve been going to both since I was 7, and they both usually have a great variety of apples and a fully-functioning autumn festival every year.

Upstate New York Fall Activities - Jack o Lanterns the author carved using pumpkins he picked upstate

Jack-o’-lanterns I carved using pumpkins that I picked upstate

Hayrides and Corn Mazes

Haunted or otherwise, hayrides are an absolute must-do when it comes to fall in upstate New York. Just like pumpkin picking, hayrides are generally a staple of most apple orchards, but they can also be found in fall festivals and markets all along the Hudson Valley. Grab a cup of piping hot apple cider and a gingersnap cookie and bundle up on a daytime hayride, or brave the night with a haunted one as you get chased through the farmlands of upstate New York.

If you’re looking for a spooky hayride, be sure to check out the Headless Horseman Haunted Hayride in Ulster Park, just two hours away from the heart of New York City … but maybe leave the kids at home.

If you prefer a nice and easy daytime hayride, try North Salem’s Harvest Moon Farm & Orchard for a more family-friendly versions of this fall activity.

Upstate New York Fall Activities - A sunflower field in New Paltz during fall.

A sunflower field in New Paltz during fall

Corn mazes. You either love them or hate them. Whether you’re hopelessly bad at directions or a human GPS, everyone can have a great time trying to navigate their way out of a corn maze. Luckily, the lush farmlands of the Hudson Valley make for an abundance of corn fields, and during the fall, these farmlands begin shedding their leaves and become dry and brittle — perfect for local farmers to shear into intricate and extensive labyrinths. Like hayrides, these can be either haunted or not, so be sure to check ahead of time to avoid some heart-stopping scares while you’re trying to find your way through.

The Lewin Farm Corn Maze is a particular favorite of mine, as it’s completely different every year, making for a good time no matter how many times you go. Schmitt’s Family Farm is another crowd-pleaser, as you can check out the harvest market and fall festival after that maze escape victory lap.

Haunted Houses

A spooky pathway in the town of Sleepy Hollow

A spooky pathway in the town of Sleepy Hollow

What fall festival would be complete without some frights? As apple picking season bleeds over into Halloween season, people ages 6 to 60 flock to these popular spots throughout the Hudson Valley, looking to get totally spooked. I’ll admit, I was never really one for a haunted house, but they’ve grown on me in more recent years, as I’ve realized that they’re generally not as scary as I once thought.

Haunted houses do always vary in intensity, so it’s important to do a bit of research before heading inside. However, they almost always follow the “no touching” rule, so not to worry. They may jump out at you or chase you with a chainsaw, but they can’t get that much closer to you!

A haunted house attraction I recommend consistently is the Horseman’s Hollow, located just an hour from the city in the haunted town of Sleepy Hollow. This little New England town has a time-honored lore of a headless horseman who terrorizes the town looking for a new head to use in place of his own. It’s a fun-filled 40-minute attraction that snakes you through the horseman’s home, grounds, cemetery, local tavern, and other places, and is suitable for kids aged 10 and up.

 Upstate New York Fall Activities - The walkway leading up to the Horseman’s Hollow

The walkway leading up to the Horseman’s Hollow

Hiking

Spooks and screams aside, there are some other fantastic fall activities you can get into while enjoying the way New York State changes during the fall season. The deep green of the region’s rolling hills give way to beautifully bright and vibrant oranges, yellows, and reds, blanketing the forest floor with crunchy brown leaves. Grab a few bottles of water, some active-wear, and catch a bus at Grand Central up to Breakneck Ridge for a heart-pounding 4-hour climb, or take a brisk walk through the Minnewaska State Park Preserve near New Paltz. Hikes up in the valley can last anywhere from 30 minutes to up to 6 hours, so be sure to do your research and look up the difficulty levels so you can adequately prepare. I really maintain that fall is the best time to hike in New York State. Nothing really quite compares — spring, winter or summer — to the colorful foliage of fall.

Upstate New York Fall Activities - The main waterfall at Minnewaska State Park Preserve.

The main waterfall at Minnewaska State Park Preserve.

Bonus: Rise of the Jack-o’-Lanterns

Although this one isn’t up in the Hudson Valley, this unique event is hosted at the Old Westbury Gardens, a quick 30-minute train ride from Manhattan. Check out hundreds of jack-o’-lanterns of all sizes, intricately carved into all sorts of shapes, designs, and characters. Walk through the picturesque grounds of the historical Old Westbury Gardens with a hot chocolate and admire the handiwork of these talented artists. This is one of those activities that sounded underwhelming to me, but wound up turning into my absolute favorite fall activity. It’s definitely worth checking out if you’ve booked flights to JFK but still want a night out of the city.

Upstate New York Fall Activities - Some intricately designed Jack o Lanterns

Some intricately designed jack-o’-lanterns

When it comes down to it, fall is one of the absolute best times of the year to visit New York State. Will you have the chance to sip rosé on a rooftop bar? Maybe not. But there are dozens of fun fall options awaiting you just a half hour away in the Hudson Valley. Grab some friends, catch a train, and get your fill of fresh fall air before winter sets in!

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Gilad Gamliel

Gilad Gamliel

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