Looking for the best Halloween activities in Westchester County, NY? If you love everything spooky, magical, and a little mysterious, Twilight Village at Philipsburg Manor in Sleepy Hollow deserves a spot on your October bucket list!
Located in the heart of Sleepy Hollow, New York, this immersive Halloween experience brings the legendary story of the Headless Horseman to life with live entertainment, fire performers, tarot card readings, delicious treats, and plenty of photo opportunities.
We recently visited, and between the colorful lighting, mysterious fog, historic buildings, and live performances, the entire village felt like stepping into a Halloween movie.
Experience the Headless Horseman in Sleepy Hollow, NY
You can’t visit Sleepy Hollow during Halloween without experiencing its most famous legend!
One of the biggest highlights of Twilight Village is the appearance of the legendary Headless Horseman, who makes a dramatic entrance during a special sound-and-light performance inspired by Washington Irving’s The Legend of Sleepy Hollow.
Visitors can also encounter characters inspired by the famous story, including Ichabod Crane and Katrina Van Tassel.
If you’re visiting Sleepy Hollow for the first time, this is one Halloween experience you won’t want to miss.
Fire Performers, Tarot Readings & Live Entertainment
There’s so much more to Twilight Village than just the Headless Horseman!
One of our favorite parts was watching the live fire performers. The combination of flames, music, colorful stage lighting, and spooky surroundings made for an incredible show.
Throughout the village, visitors can enjoy:
- Live fire performances and entertainment
- Tarot card readings and fortune tellers
- Storytelling and legendary characters
- A roaming brass band
- A pop-up marketplace featuring handmade goods and unique finds
- Halloween-themed photo opportunities
- Food trucks, sweet treats, cocktails, and mocktails
Tarot readings are offered in limited quantities on a first-come, first-served basis, so plan accordingly.
S’mores, Food Trucks & Halloween Treats
What’s a fall night without something delicious?
Twilight Village features food vendors offering bites and beverages throughout the evening. You can also enjoy seasonal treats like s’mores, perfect for getting into the Halloween spirit.
Special FLEX tickets include a complimentary s’mores kit and hot chocolate or cider. Food and drinks are otherwise available for purchase.
Whether you’re heading out for a Halloween date night, catching up with friends, or spending the evening with family, there’s something here for everyone.
Is Twilight Village Kid-Friendly?
Yes! Twilight Village at Sleepy Hollow is recommended for all ages, making it a great option for families looking for Halloween activities in Westchester County.
Unlike a traditional haunted house focused entirely on scares, Twilight Village combines spooky atmosphere, interactive entertainment, and storytelling.
That said, younger children may find some of the darker settings, loud effects, and the Headless Horseman’s appearance a little intense.
Westchester Blogger Tip: Wear comfortable shoes, dress for the weather, and bring a stroller that’s suitable for uneven outdoor pathways if you’re visiting with little ones.
Twilight Village Sleepy Hollow 2026: Dates, Location & Tickets
Location: Philipsburg Manor, 381 North Broadway, Sleepy Hollow, NY 10591
Dates: Select evenings, October 2–31, 2026
Hours: Evening times vary by date, generally beginning at 6:00 or 6:30 PM.
Tickets: Approximately $25–$35 for standard admission, depending on ticket selection.
Duration: Plan for approximately 45 minutes, although you may want additional time to enjoy food and browse the market.
Ages: Recommended for all ages.
Important: Tickets must be purchased in advance and are not sold on-site. Popular evenings can sell out.
Purchase tickets: https://hudsonvalley.org/events/twilight-village-at-sleepy-hollow/
Is Twilight Village Worth Visiting?
If you’re searching for fun things to do in Sleepy Hollow during Halloween, I definitely recommend checking it out.
What makes Twilight Village special is the atmosphere. The glowing historic buildings, colorful lights, mysterious fog, live performances, and legendary characters create such a memorable experience.
It’s perfect for a fall date night, a weekend adventure with friends, or a family outing.
And of course, getting to see the Headless Horseman in the town where the legend became famous is pretty cool!
My recommendation: Add Twilight Village at Philipsburg Manor to your Halloween 2026 bucket list, grab your tickets ahead of time, and don’t forget your camera.
For more Halloween events in Westchester County, fall festivals, family-friendly activities, local restaurants, hidden gems, and things to do throughout the Hudson Valley, visit www.WestchesterBlogger.com.
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