I’m already excited to tell you: the Tarrytown (Sleepy Hollow area) Halloween Parade will take place on Saturday, October 25, 2025, at 5:00 PM.
It’s the annual main event that brings together costumed marchers, floating creativity, and block‑party fun all set in the legendary Hudson Valley. It’s free to watch, and you can even register to participate with your own float or theme group.
This parade isn’t just any Halloween gig. It’s held in Patriots Park, the actual spot Washington Irving referenced in The Legend of Sleepy Hollow as “Wiley’s Swamp,”
where Ichabod Crane encounters the Headless Horseman Visit Sleepy Hollow.
That blend of spooky history and community spirit is what gives it real character and why I’m so keen to share it with fellow Halloween fans like you.
Sleepy Hollow Halloween Parade | Date, Route
| Detail | Info |
|---|---|
| Date & Time | Saturday, October 25, 2025 • 5 PM |
| Location / Route | Starts at Patriots Park, Tarrytown • Marches south along Broadway to Main Street |
| Duration | About 1 hour (5 PM – 6 PM) Visit Sleepy Hollow |
| Entry Fee | Free to view • Registration required to participate |
| Participation | March with a themed float or group register to be eligible for prizes |
| Post-Parade | Block party on Main Street with DJs, live music, outdoor dining, performers |
| Parking Advice | Extremely limited use Metro-North or Westchester buses |
| Organizer | Village of Tarrytown, Sleepy Hollow–Tarrytown Chamber of Commerce |
Why This Parade Hits Different (Friendly Insight & Personal Touch)
I have to say, what makes this parade stand out isn’t just the spooky vibe it’s how it weaves local legend, community, and Halloween fun into one memorable evening.
Starting at the site tied to Ichabod Crane’s eerie encounter gives it a goosebump-worthy storytelling edge.
The route itself is cozy but lively: a one-hour march from Patriots Park down Broadway, then into a block-party on Main Street.
I love that it’s short enough to fit into family plans, but big enough to feel festive. And yes even I might sign up next year to march with a float (because who doesn’t want a shot at a prize for best costume or float?).
How the Parade Began | From Small Spark to Big Event
I genuinely love knowing that the Tarrytown Halloween Parade started as a modest event back in 2002. It was a small-scale local celebration with just a handful of floats and participants hard to imagine now, right?
It didn’t take long for the vibe to catch on. Within a few years, what began as a quiet local gathering grew into a major regional festivity. Today, the parade draws thousands of people from all over Westchester and beyond.
Milestones and Growth | Becoming a Halloween Institution
By 2024, the parade had become what I’d call a full-blown spectacle. That year, there were about 110 entries, including floats, bands, stilt walkers, and entertainers.
Over 900 people marched. The costumes and creativity just kept getting wilder.
Crowds lined the route with zero room to spare. Main Street transformed into a dense, festive sea of people by early evening such a fun chaos. Hudson Indy It’s clear that over the years, the parade has upped its game big time.
Cultural Backdrop | Why Sleepy Hollow Loves Halloween
The legend of Sleepy Hollow wouldn’t be the same without Washington Irving. His 1820 story is the reason the parade exists at all.
Irving wrote that eerie tale while in England but set it right here along the Pocantico River. The Headless Horseman and that gothic graveyard set the perfect mood. Sleepy Hollow embraces that vibe.
Local Connection | Venue Rooted in Legend
I always get goosebumps over this: the parade kicks off at Patriots Park, which legend calls “Wiley’s Swamp” the very site where Ichabod Crane first saw the Headless Horseman in Irving’s story.
Framing the parade here gives it a touch of literary magic. That connection to storytelling and local legend makes the parade feel both fun and meaningful at the same time.
Halloween Season | More Than Just the Parade
The parade is major, but it’s just one star in Sleepy Hollow’s Halloween constellation. October brings haunted hayrides, pumpkin festivals, glowing jack-o’-lantern trails, ghost tours, and candlelit mansion nights at spots like Philipsburg Manor and Lyndhurst.
Sleepy Hollow Country is branded as a Halloween mecca and for good reason. The parade fits snugly into a broader celebration of autumn, lore, and local history.
Visual: Simple Route Map
(A visual of the parade route: starting at Patriots Park, down Broadway, ending at the Main Street block party.)
This simple visual lets readers immediately grasp how the event flows super helpful for folks planning where to watch or meet up.
How to Participate in the Sleepy Hollow Halloween Parade 2025
If you’ve ever dreamed of walking in a Halloween parade, this is your chance. Anyone can register whether you’re a solo character, a group of friends, or part of a community organization. Registration is required if you want to march, and spots can fill up fast.
There’s no fee for individual walkers, but floats and large groups may have guidelines for size and setup.
The organizers welcome everything from spooky costumes to whimsical themes. Just make sure your entry is family-friendly and safe.
Once registered, you’ll receive check-in details and your lineup spot. Arrive early so you have time to assemble your group or float before the 5:00 PM start.
Costume Guidelines and Contest Prizes
Costumes are the heart of this parade. While there’s no strict theme for 2025, originality is always celebrated.
The judging panel awards prizes for best costumes and floats, and past winners have included everything from life-size puppets to clever Headless Horseman spins.
Avoid props that could pose safety risks sharp objects, open flames, or anything that could trip a marcher. If your costume includes lights, double-check battery life before stepping off.
Best Viewing Spots for Spectators
If you’re not marching, your best bet is to arrive early along Broadway between Patriots Park and Main Street. The corner near the Sleepy Hollow–Tarrytown border gives you a perfect view of floats turning onto Main Street.
For less crowded areas, head further down Broadway where fewer restaurants and bars attract big sidewalk crowds. Families with young kids often prefer the start of the route near Patriots Park it’s easier to find space there.
Accessibility and Family Tips
The route is flat, making it accessible for strollers and wheelchairs. If you need ADA seating, contact the parade committee in advance. Dress warmly late October evenings in the Hudson Valley can be chilly.
Bring water and snacks if you’re with kids, and have a meeting spot in case you get separated. The block party can be busy, so keeping your group together is easier if you choose a landmark to gather by.
Main Street Block Party Highlights
The celebration doesn’t end when the parade does. Main Street transforms into a lively block party with outdoor dining, live DJs, street performers, and costumed characters roaming the crowd.
Restaurants and bars often offer themed menus, from pumpkin-spiced cocktails to ghost-themed desserts. It’s a great way to end the evening whether you’re grabbing a drink with friends or treating the kids to warm cider and a caramel apple.
Travel and Accommodation Tips for Out-of-Town Visitors
If you’re traveling in for the parade, plan ahead October weekends in Sleepy Hollow and Tarrytown book up quickly.
The closest hotels include Tarrytown House Estate, Castle Hotel & Spa, and SpringHill Suites by Marriott. Each offers easy access to the parade route and the area’s other Halloween attractions.
The nearest train stop is Tarrytown Station on the Metro-North Hudson Line. From there, you can walk or take a short cab ride to Patriots Park. For drivers, parking is very limited near the route, so it’s best to park outside the core and walk in.
Parking and Public Transport Advice
Street closures on Broadway and Main Street begin in the afternoon, so plan your arrival early. Metered parking fills up quickly. A better option is to use the Metro-North train from Grand Central Terminal or buses from surrounding towns.
If you must drive, consider parking at the Tarrytown Metro-North lot or other public lots a few blocks away. Wear comfortable shoes you’ll likely walk a bit to your viewing spot.
Safety and Event Rules
The parade is family-friendly, but security is taken seriously. Bag checks may be in place at certain entry points. Avoid bringing alcohol, glass bottles, or any items that could be considered weapons.
Pets are allowed only if they’re well-behaved, leashed, and used to crowds. Parents should keep kids close, especially during the busy block party. Having a pre-arranged meeting spot is smart in case someone gets separated.
Photography and Social Media Tips
If you want the best photos, position yourself where the parade turns onto Main Street performers often play to the crowd there. For daylight shots, arrive early to catch the pre-parade lineup in Patriots Park.
By the time floats reach Main Street, the sun is usually setting, giving you a warm, golden backdrop. At night, use your camera’s night mode or a fast lens to capture clear shots without flash.
Don’t forget to tag the official event pages and use popular hashtags like #SleepyHollowHalloween and #TarrytownParade to join the online conversation.
Conclusion
Every October, the Sleepy Hollow Halloween Parade blends small-town warmth with legendary lore. Between the iconic setting, creative costumes, and lively block party, it’s an evening that captures the magic of fall in the Hudson Valley.
Whether you’re marching in costume or cheering from the curb, you’ll leave with the feeling that you’ve stepped into a living story one that keeps growing every year.
If you’re looking for an authentic Halloween experience with personality and history, this parade belongs on your calendar.
FAQs
Yes, it’s free for all spectators.
No ticket is needed, but registration is required for participants.
By 4 PM to get a good viewing spot.
Near Patriots Park for fewer crowds, or Main Street for the party vibe.
Yes, but keep children close, especially during the block party.