The Best Fall Activities in the Hudson Valley 🍂
Fall in the Hudson Valley is one of those seasons where there is so much to do that it can be hard to decide where to start.
If you're looking for things to do this fall, here’s what I’d suggest adding to your list—from unique ways to see the fall foliage and scenic train rides to apple picking, fall festivals, historic sites and, of course, plenty of spooky-season fun.
Whether you're planning a day trip, a weekend getaway or just looking for something new to do close to home, these are some of the fall activities I'd put at the top of my list.
🍂 See the Fall Foliage from the Railroad Tracks
Want to experience the Catskills foliage in a way that's a little different?
Head to Catskills Rail Explorers and pedal your way along the railroad tracks surrounded by the changing leaves.
It's an active and unique way to take in the scenery and makes for a particularly fun fall outing with friends, family or a date.
Afterward, I'd head into Phoenicia for breakfast or lunch at Phoenicia Diner. Because a fall adventure always needs a good food stop.
🚂 Take a Scenic Train Ride Through the Catskills
Another way I'd suggest experiencing fall foliage? Take a train ride through the mountains.
The Catskill Mountain Railroad offers seasonal rides through the Catskills, giving you the chance to sit back and enjoy the scenery without worrying about navigating the roads.
If you're looking for a quintessential Hudson Valley fall experience, this is definitely one to add to your list.
🍎 Go Apple & Pumpkin Picking
Of course, you can't talk about fall in the Hudson Valley without talking about apple picking and pumpkins.
Head to one of the region's many orchards and farms to spend the day picking apples, searching for the perfect pumpkin, grabbing cider donuts and exploring the farm markets. Many orchards also include hayrides, petting zoos, corn mazes, and activities for the kids.
This is one of those fall traditions that never gets old—and there are farms throughout the Hudson Valley, so you can easily make it part of a day trip or weekend. Some of my favorites include: Maskers Orchard and Ochs Orchard in Warwick, Soons Orchard in New Hampton, and Jones Farms in Cornwall.
🎨 Go to a Fall Festival or Craft Fair
Another thing I'd suggest doing this fall: put a few local festivals on your calendar.
The Hudson Valley has no shortage of fall festivals, harvest celebrations, street fairs and craft markets.
You can spend the day browsing local vendors, shopping from small businesses, eating seasonal food and enjoying live music and other activities.
Bethel Woods Harvest Festivals are another destination worth keeping an eye on for seasonal events and fall activities.
And don't overlook the smaller town festivals and craft fairs happening throughout the region—they're often a great way to discover a new Hudson Valley town.
🎃 Get Into the Halloween Spirit at The Great Jack O'Lantern Blaze
If you love Halloween, this one is a must.
The Great Jack O'Lantern Blaze at Van Cortlandt Manor transforms the historic property into an incredible nighttime experience featuring thousands of illuminated, hand-carved pumpkins.
It's one of those Hudson Valley fall experiences that feels completely different once the sun goes down.
And yes, I absolutely think it's worth adding to your fall bucket list.
👻 Spend a Fall Day Exploring Sleepy Hollow & Tarrytown
And then there's Sleepy Hollow—which might be one of the most iconic places to visit in the Hudson Valley during the fall.
Start by learning about the area's history and connection to Washington Irving with a historic walking tour through Sleepy Hollow and Tarrytown.
The Sleepy Hollow & Tarrytown Historical Society offers TarryHollow walking tours that explore the area's history, including the Old Dutch Church and its historic burying ground.
Then spend some time exploring Sleepy Hollow Cemetery, which has its own fascinating history and is especially atmospheric during the fall. Sleepy Hollow Cemetery spans 90 rolling acres and functions as both a historic final resting place for icons like Andrew Carnegie, Washington Irving, Walter Chrysler, and Elizabeth Arden, as well as an accredited Level 1 Arboretum
You can also walk along the Hudson River to see the Sleepy Hollow Lighthouse, go to the TaSH Farmers Market on Saturdays, or visit Philipsburg Manor to step back in time and experience one of the area's historic properties.
And if you're visiting during Halloween season, there are even more spooky and historic experiences to add to your itinerary.
🏛️ Visit the Armour-Stiner Octagon House in Irvington
If you haven't visited the Armour-Stiner Octagon House in Irvington, I'd add this one to your fall list.
This incredibly unique, eight-sided Victorian house is a National Historic Landmark and one of the Hudson Valley's most unusual historic properties. Built in the 19th century and restored to its 1870s appearance, the house is filled with ornate architecture and fascinating history.
And fall is an especially fun time to visit.
The Armour-Stiner House offers seasonal experiences that lean into the property's mysterious history, including Myths & Mysteries of The Octagon House, The Lady in White, and 'Tis the Wind and Nothing More. The 2026 fall programming runs into the Halloween season.
It's the kind of place that feels like it belongs in a fall movie—and it's a great addition if you're looking for something beyond the usual pumpkin patches and foliage drives.
🍁 Hudson Valley Fall Bucket List Plans:
If you're wondering where to start, here's how I'd narrow it down:
🍂 For foliage: Catskills Rail Explorers - Phoenicia, NY
🥞 For a food stop: Phoenicia Diner - Phoenicia, NY
🚂 For a scenic experience: Catskill Mountain Railroad - Kingston, NY
🍎 For a classic fall day: Apple & pumpkin picking, hayrides, corn mazes, petting zoos, and apple cider donuts
🎨 For shopping local: Fall festivals and craft fairs
🏛️ For something unique: Armour-Stiner Octagon House
🎃 For Halloween: The Great Jack O'Lantern Blaze
👻 For history: Sleepy Hollow & Tarrytown
🏡 For a historic experience: Philipsburg Manor -Sleepy Hollow, NY
🌊 For a scenic walk: Sleepy Hollow Lighthouse
The best part about fall in the Hudson Valley is that you don't have to choose just one. There are enough activities, towns, farms, festivals and attractions to keep you busy all season long.
Save this guide, grab your crew, and start planning your Hudson Valley adventures. 🍂