Halloween in NYC: Village Parade and a Spooky Drive to Sleepy Hollow

Halloween in New York isn’t just a holiday - it’s a full-blown vibe. Picture this: loud music, wild costumes, street parties, and an ocean of people dancing down the avenues. Now add a dash of mystery - Sleepy Hollow, the home of the Headless Horseman, wrapped in fall colors and ghostly legends. Sounds perfect, right?

Here’s the plan for your ultimate Halloween weekend: enjoy the legendary Greenwich Village Parade, then hit the road for a cozy, spooky escape to Sleepy Hollow. Everything you need for a perfect Halloween adventure - right here.

Part 1: The Greenwich Village Halloween Parade

When and where it happens

If you’ve never been to the Greenwich Village Halloween Parade, trust me - you need to fix that. It’s happening on October 31, 2025, from 7:00 PM to 11:00 PM. The parade marches up 6th Avenue from Spring Street to around 15th or 16th Street.

It’s not just a parade of costumes - it’s a full-on show. Giant puppets, street performers, and every kind of outfit imaginable. Some are scary, some are hilarious, some are pure art.

Best spots to watch

If you don’t want to get lost in the crowd, show up early. The best viewing spots? Near Spring Street or W Houston, right at the start, or at the end around 14th–15th Streets. These areas are usually less packed, so you can actually breathe and enjoy.

Photographers, bring your camera - the giant puppets and over-the-top costumes are a dream to shoot.

Bringing kids? Aim for the quieter end of the route and get there by 5:30 PM. It’s less noisy, but still packed with Halloween magic.

Parking (aka the nightmare before the parade)

Parking in NYC on parade night? Yeah… good luck with that. Streets start closing around 6:30 PM, garages fill up hours before, and prices jump faster than a vampire at midnight.

Here’s the move: rent a car with Drivo and skip the parking drama. You’ll have full control of your trip without circling blocks or stressing over road closures. Just enjoy the parade and save your sanity.

Part 2: From the City to the Legend - the Drive to Sleepy Hollow

The best route

Once you’ve soaked up the parade energy, hit the Palisades Interstate Parkway toward Sleepy Hollow. It’s the most scenic way there - rolling hills, fiery fall leaves, and Hudson River views that make you want to pull over just to stare for a while.

The drive takes about 40–60 minutes outside rush hour, which is perfect for a chill evening cruise.

Must-see stops

Want to make the trip even better? Stop at:

• Palisades Parkway Scenic Overlook - incredible photo spot with river and mountain views.
• Pumpkin Patch or Farm Stand - grab a pumpkin or two, maybe some cider doughnuts or apple pie for the road.

How to dodge traffic

October weekends can get busy. The trick is to leave early morning (before 7 AM) or later at night (after 8 PM). And when you’re heading back, do it Sunday morning - not Sunday night. Trust me on this one.

Part 3: What to Do in Sleepy Hollow and Tarrytown

The must-see Halloween stuff

First stop: The Great Jack O’Lantern Blaze at Van Cortlandt Manor. Over 7,000 carved pumpkins glowing in the dark - it’s surreal. Tickets sell out super fast, so grab them early.

Then check out the Sleepy Hollow Cemetery Tours. It’s a mix of history, mystery, and goosebumps in the best way. Bring a flashlight - it makes the experience way more fun.

And don’t skip the Headless Horseman Bridge. The original is gone, but the wooden replica still has that eerie charm straight out of legend.

Family fun

Got kids with you? Try the Haunted Hayride - spooky but not too scary (depending on your crew). Or hit the Beekman Avenue street fair for games, snacks, and a lot of local energy.

Where to eat

When you’re ready to refuel:

• Horsefeathers (Tarrytown) - friendly spot with solid comfort food.
• Bridge View Tavern (Sleepy Hollow) - cozy pub vibes, great beer, great burgers.
• Hudson Farmer & The Fish (Sleepy Hollow) - go here if you want something fancier with a killer river view.

Part 4: The Right Car for the Ride

Why a rental just makes sense. If you want a smooth, flexible trip, renting through Drivo is a no-brainer. You move on your own schedule, skip the parking stress, and just enjoy the road.

Pick your ride. Couple’s getaway? A compact sedan is perfect. Family or friends’ trip? Grab an SUV - you’ll have room for everyone (and a few pumpkins too).

Transparent pricing, no surprises. With Drivo, what you see is what you pay. No hidden fees, no “surprise” charges later. Insurance and taxes? Already included. Just pick your car, hit the road, and enjoy.

Conclusion

Don’t let logistics kill your Halloween mood. Rent your car with Drivo, chase some legends, and make this Halloween one for the books - your own wheels, your own pace, your own adventure.