If you live in Westchester, you already know: Halloween around here is not just one night. It’s practically a season.

And nobody does it quite like Sleepy Hollow Country.

The Great Jack O’Lantern Blaze is back for 2026, but this year I wouldn’t think of it as just going to see the pumpkins. Historic Hudson Valley has basically created an entire Halloween itinerary — and I’m already trying to figure out how many of these I can fit in.

🎃 The Great Jack O’Lantern Blaze Is Bigger Than Ever

Let’s start with the classic.

The Great Jack O’Lantern Blaze returns to Van Cortlandt Manor in Croton-on-Hudson for 44 nights, September 18 through November 8, and this year it has its longest trail ever.

Thousands of individually hand-carved, illuminated jack o’ lanterns transform the historic property into one of those experiences that somehow manages to be spectacular whether you’re bringing kids, friends, a date — or you’re like me and simply love a good fall night out.

And there are some fun new additions this year.

👻 Creature Feature Forest

This may be the one I’m most curious about.

The new Creature Feature Forest is inspired by Van Cortlandt Manor’s history as the site of a drive-in movie theater in the mid-20th century.

Think classic movie monsters — made entirely out of pumpkins.

I need to see this.

📚 Literary Lane

There’s also a new Literary Lane, where familiar children’s stories and fables are reimagined in glowing pumpkin displays.

And on the lawn of the manor house, there’s an interactive dance party.

Because apparently looking at pumpkins wasn’t enough. Now we’re dancing with them.

I’m in.

💰 And There Are $24 Nights!

This caught my attention.

Blaze has expanded its value pricing this year, with tickets available for just $24 on select evenings.

Considering how expensive an evening out can get, that’s worth knowing — especially if you’re taking the whole family.

🍸 Yes, There Are Cocktails

You knew I was getting to this part.

The VIP Gourd & Goblet Tavern returns along the pumpkin trail. It’s a sit-down experience inside an 18th-century inn with snacks, cocktails and mocktails.

The Headless Horseman’s Hideaway is back too, with festive snacks, cocktails or mocktails and photo opportunities with the Headless Horseman.

And new this year is Monster’s Mug, a quick drink stop right along the trail.

Suddenly pumpkin viewing has become quite civilized.

But Don’t Stop at Blaze

Here’s what I really like about this year’s lineup.

You could make an entire October of this.

Sleepy Hollow Country has several completely different Halloween experiences happening throughout the season.

🐎 Solve the Mystery of Ichabod Crane

The Headless Horseman Files: A Sleepy Hollow Whodunit is back with an expanded schedule.

You walk through Philipsburg Manor for about 45 minutes, meet suspicious characters, collect clues and decide for yourself what actually happened to Ichabod Crane.

Basically: Halloween meets murder mystery.

🔥 Twilight Village at Sleepy Hollow

Also at Philipsburg Manor, Twilight Village returns with even more vendors and activities.

There will be food, drinks, shopping, traveling musicians, performers, storytellers and fire performers — plus a dramatic sound-and-light recreation of the Headless Horseman’s midnight ride.

This sounds like a great one for a group.

✨ A Night of Magic

The Spirits of Sleepy Hollow Country: A Night of Legendary Magic brings nationally known illusionists Mark Clearview and Nick Wallace to Philipsburg Manor with new magic, special effects and plenty of audience participation.

And yes, snacks and cocktails are available here too.

I’m sensing a theme, and I approve.

📖 Hear The Legend of Sleepy Hollow Where It All Began

This one feels particularly special.

At Washington Irving’s Sunnyside, storyteller Jonathan Kruk, accompanied by musician Jim Keyes, performs Washington Irving’s The Legend of Sleepy Hollow outdoors on Irving’s own estate.

There are also daytime Legendary Tours of Sunnyside, including a tour of the cottage, an original shadow-puppet film and a special exhibit devoted to The Legend of Sleepy Hollow.

When you live here, it’s easy to forget that people travel from all over the world for this history.

We have it practically in our backyard.

🖤 And Then There’s Poe…

For something decidedly more grown-up, An Audience with Poe returns to the Historic Hudson Valley Library.

It’s an evening of Edgar Allan Poe storytelling paired with cocktails and themed treats, featuring haunting renditions of classics including The Raven, The Tell-Tale Heart, The Black Cat and The Masque of the Red Death.

Cocktails and Edgar Allan Poe?

Now that’s my kind of book club.

So…Which One Are We Doing?

Blaze is obviously the Westchester fall tradition, but I think 2026 may be the year to add something else to the itinerary.

Do Blaze and cocktails.

Solve the Ichabod Crane mystery.

Spend an evening at Twilight Village.

Listen to The Legend of Sleepy Hollow at Washington Irving’s actual home.

Or have cocktails with Edgar Allan Poe.

Actually, why are we choosing?

October is 31 days long.

The Details

The Great Jack O’Lantern Blaze: Hudson Valley
📍 Van Cortlandt Manor
525 South Riverside Avenue
Croton-on-Hudson, NY

🎃 Blaze dates: September 18–20 and 25–30; October 1–31; November 1 and 6–8.

Other Sleepy Hollow events take place on select dates throughout October.

Tickets for all events are limited, and advance purchase is required. Many dates regularly sell out.

My advice? Don’t wait until October 30 and suddenly decide you want to celebrate Halloween. You know who you are.