Halloween in Westchester 2026: Events, Parties & Safe Rides

When it comes to Halloween, Westchester doesn’t do subtle – and Sleepy Hollow doesn’t do quiet. Home of the Headless Horseman legend, our corner of the Hudson Valley turns into the Halloween capital of the East Coast every October. Here’s what’s on in 2026, plus how to get there and back safely.

Can’t-Miss Halloween Events in 2026

The Great Jack O’Lantern Blaze

More than 7,000 hand-carved, illuminated jack o’lanterns light up Van Cortlandt Manor in Croton-on-Hudson. 2026 dates run September 20 through October 31, plus select November dates. Tickets are timed-entry and sell out – book early.

Horseman’s Hollow at Philipsburg Manor

Sleepy Hollow’s haunted attraction brings Washington Irving’s legend to life across 16 evenings: October 4-6, 11-13, 18-20, 25-27, 31 and November 1-3. Not for the faint of heart – recommended for ages 10 and up.

Sleepy Hollow Haunted Hayride & Block Party

On October 16 and 17, Beekman Avenue shuts down for a free block party from 5 PM with live music and food vendors, followed by ticketed haunted hayrides at 7 PM through the streets near Sleepy Hollow Cemetery.

Irving’s ‘Legend’ at the Old Dutch Church

Master storytellers perform The Legend of Sleepy Hollow at the circa-1685 Old Dutch Church on select dates October 4-31. An only-in-Sleepy-Hollow experience.

Your Halloween Night Ride Guide

Between costumes, groups, and late nights, Halloween is the one night you should never drive yourself. A pre-booked private car means:

• No parking nightmares – event parking near Sleepy Hollow sells out and fills fast
• Your whole crew, one car – SUVs for groups heading to parties together
• A guaranteed ride home – no surge pricing, no waiting on an app at midnight
• Costume-friendly – plenty of room, no questions asked

Dia Limo Service runs 24/7 through Halloween weekend from our Dobbs Ferry base – minutes from Sleepy Hollow, Tarrytown, Irvington, and all of Westchester.

Halloween Special: $20 Off Airport Round Trips

Flying out for Halloween – or flying home? Get $20 off any airport round trip booked October 25 through November 1. Just mention code BOO20 when you book. Flat rates, flight tracking, and 24/7 chauffeurs to JFK, LaGuardia, Newark, and Westchester County Airport.

Halloween Ride FAQs

Do you operate on Halloween night itself?

Yes – 24/7, including October 31. Pre-booking is strongly recommended for Halloween weekend.

Can you take our group to Horseman’s Hollow?

Absolutely – we do drop-offs and pickups at Philipsburg Manor, Van Cortlandt Manor, and all event venues. Book a round trip so your ride home is already secured.

Does the BOO20 code work for non-airport rides?

BOO20 is valid on airport round trips booked October 25-November 1. Call us for party-night flat rates.

Planning your Halloween night? Book your ride with Dia Limo Service – call (914) 292-4800, WhatsApp us, or use our online reservation form.