Autumn in New York: Escape to the Hudson Valley and Catskills

Hike Kaaterskill Falls & Window Shop in Tannersville

Kaaterskill Falls is an extremely popular hiking destination during fall foliage season, and for good reason. This 260-foot two-tier waterfall has been documented in countless paintings, movies and photographs, becoming one of the most iconic destinations in all of the Catskills. You’ll likely need to pay around $20 for parking at a nearby home or business as the official lots fill up quite early. You can also consider taking the Kaaterskill Trolley for $10 from downtown Tannersville, the small ski town next door, which is home to a small stretch of locally owned shops and restaurants.

Drink at the Angry Orchard Cider House

Just 90 minutes out of Manhattan, you can find yourself at Angry Orchard’s 60-acre farm. I love this awesome location because there’s absolutely no admission fee. You can wander through their apple orchards (though you can’t pick any—those apples are saved for their cider), hang out around the fire in their backyard, listen to live music, and—best of all—sample their apple cider flights entirely for free. If you’d like, you can purchase larger glasses, any of their limited-edition ciders or pay to take a tour of their cidery and learn how the cider is made. Both times I’ve visited, I also spent $5 on their apple cider donuts to pair with my cider flight. The donuts may be some of the best apple cider donuts I’ve ever had—they’re made fresh in front of you, dunked in cinnamon or maple sugar, and completely melt in your mouth when you eat them. On weekend evenings in the fall, they often have food trucks on-site for visitors to enjoy.

Take a Sleepy Hollow Cemetery Tour & Visit the Great Jack O’Lantern Blaze

Embark on a captivating journey through Sleepy Hollow Cemetery, illuminated by the soft glow of kerosene lanterns. This immersive two-hour tour transports you to a bygone era, offering a fascinating overview of the cemetery’s storied past, showing off its famous art and architecture and visiting the graves of iconic figures such as industrial magnates Andrew Carnegie and William Rockefeller as well as Washington Irving—the author whose famous spooky tale gave Sleepy Hollow its legendary name.

Afterwards, drive 15 minutes north and pop in to the Hudson Valley’s Great Jack O’Lantern Blaze, an annual event where over 7000 illuminated hand-carved pumpkins are put on display across the estate of the Van Cortlandt Manor in Croton-on-Hudson. Check the website to be sure that they’re not sold out! This is one of the most popular spooky season events in the region.

Explore Warwick AppleFest

About an hour outside the city, the quaint town of Warwick hosts an Apple Festival every year. This festival brings craftspeople, musicians, artists, and food vendors together to celebrate autumn. There is an apple pie baking contest (and a subsequent apple pie eating contest), face-painting and henna, raffles and auctions, and many delicious apple-themed treats. We helped ourselves to apple slices smothered in caramel and peanuts after enjoying a day of wandering through the lively festival.

Breathe in the Fall Air at Storm King Art Center

Storm King is open all year round, but visiting during the autumn is a popular New Yorker's pastime. Nearly everyone has taken a fall trip up to Storm King to take in the absolutely stunning trees as their leaves begin to turn colors. Storm King is a 500-acre sculpture park; expect to spend your day walking for miles and still not see all of this beautifully photogenic place. Make sure to visit the adorably artsy town of Beacon, NY while you’re nearby. The Metro-North Railroad even offers special day passes that include transportation across the river to Storm King after arriving in Beacon!

Pick Apples at Jenkins-Lueken Orchard & Hike to Awosting Falls

When in the Hudson Valley, you have to go apple picking. Over the years, my wife and I have finally settled on our favorite upstate apple orchard: Jenkins-Lueken Orchard in New Paltz, NY. We like this orchard because it’s small enough to be manageable, but sizable enough to boast a wide variety of apples. We also loved its laid-back vibes; after we asked the attendant what kind of apples were on which trees, she answered by saying, “Don’t forget to take a bite just to make sure you like them!” We got to spend the next hour wandering through the rows of trees, tasting and picking whatever we liked. The prices were affordable, and they didn’t require a minimum amount of apples—you could pick as many or as few as you’d like. Jenkins-Lueken Orchard also happens to be situated right beside Minnewaska State Park, so make a day of it and visit the beautiful Awosting Falls after you satiate yourself with fresh-picked apples and don’t forget to swing through the quaint college town of New Paltz, NY for dinner on your way home.

Get Scared at the Burn Brae Mansion Dark Forest Fright Walk

Ready to face your fears? Embark on a spine-chilling journey through the eerie woods surrounding the historically haunted Burn Brae Mansion. From witches and monsters to ghosts and goblins, the trail is teeming with Halloween’s most terrifying figures. I’m not going to lie—it was cheesy but still so fun. I’m not a huge fan of these types of fall attractions, but they sufficiently scared me without overdoing it. I also love that they offer a family-friendly option, “the Dark Forest Children’s Matinee.” Enjoy live music, food, and a selection of beer and wine from local vendors while you’re there. Feeling daring? Extend the fright and spend the night at the Haunted Burn Brae Mansion.

Creek Bar Catskills, Mountain Dale

Find the painted sign stating “We’re in the woods” and follow the arrow down the path to the bar in the back. Have some BBQ and a drink by a campfire in the woods under the falling leaves while the band on stage plays.

Westwind Orchard, Accord

One of my favorite spots in all of the Catskills. Sit in an orchard by the fire eating fresh Italian food and sipping your cider while live music plays, the sun sets and that brisk autumn breeze rolls in. What more do I have to say? Maybe the home-made gelatos and sorbets will sell you?

Tabla, Tannsersville

If you’re looking for a more upscale dining experience while upstate, this is the place. Owned and operated by Brooklyn restaurateur David Schneider, this Mediterranean taverna has consistently been rated one of the best restaurants in the Catskills since it opened in 2021.

Mama’s Boy Burgers, Tannersville

Adorable little burger and ice cream shack. I can’t pass through town without grabbing some of their cheese curds.

Phoenicia Diner, Phoenicia

Classic American diner with a modern menu. Operating in the Catskills since the 80s. Try the “Catskills Muddy Water” coffee.

Harana Market, Accord

A popular Filipino Deli and Asian Market located in an old barn. Don’t miss the lumpia.

Bread Alone Bakery, Woodstock

Delicious bread and pastries made fresh in-house daily.