CUE THE SPOOKY MUSIC
There...that's better!
Although a Halloween trip wasn't in the cards for us this year, I thought I'd bring you a
Halloween trip we've taken in the past, that's only about an hour from Jay's home - Sleepy Hollow, New York. It's a little village in the Hudson Valley that eats, lives and breathes Halloween 365 days a year and the former home of Washington Irving, the famed author that wrote The Legend of Sleepy Hollow. You know...Headless Horseman, Ichabod Crane and all that.
Many people believe Salem, MA is THE place to be on Halloween. No thanks. You can keep their $600 per night hotel rooms that skyrocket to $3500 per night to fleece their Halloween visitors.
Sleepy Hollow's contingent of only 11,000 full time residents has brought Sleepy Hollow/Tarrytown and the surrounding area to the forefront of the Halloween stage, managing to draw in over 100,000 visitors in the month of October alone. That's quite a feat for a small village of 11,000 people! And they manage to do it without charging $3500 a night for accommodations!
Back Story
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Jay and Kendall
Jay and his brother, Jude have a doctor friend (Kendall) in Indianapolis who volunteers at the Wellness Fair that's part of Indianapolis' Halloween Festival.
He asked Jay and Jude to join him to volunteer at that Wellness Fair - which they were only too happy to do.
With one small problem - Jay had already put together a surprise birthday trip for me to Sleepy Hallow. Now what to do?
When he told me about this Wellness Fair and the surprise trip he'd planned for me, I said "Why can't we do both? We can fly to Indianapolis, do the Wellness Fair, then fly to Sleepy Hollow and since we do a lot of work for Make a Wish Foundation, they have an event there that we can also volunteer for. Then plan the rest of the Halloween festivities around our volunteering."
So you don't get confused here, there's two Irvington's - one is a neighborhood of Indianapolis where this Wellness Fair is held and the other is a village near Sleepy Hollow and Tarrytown in the Hudson Valley of New York. They each hold their own Halloween festivals.
I should also mention that at one time Sleepy Hollow and Tarrytown were the same village - until Tarrytown split off to become its own village. They adjoin one another and are close enough to one another that you can walk between them. Both villages are easily walkable but you might want to do what we did and bring your bicycle along. You can also rent a bike.
Since 2013, New Yorkers have been able to use an app to pay a nominal fee to liberate the bike from a designated station, hop on and, when done, drop it off at another bike station near their destination.
Now residents of Sleepy Hollow and Tarrytown (age 18 and older) can take advantage of a similar bike sharing program, but one that uses e-bikes that provide an extra electrically powered oomph, thus taking the bite out of the Hudson Valley’s many steep streets.
The e-bikes are stationed at a dozen locations around Sleepy Hollow and Tarrytown (see map below), including the Metro North station west of the tracks and as far removed as the parking lot on the southwest end of the Tarrytown lakes.
Project Mover bikes can be accessed through a downloadable app. Each bike has a QR code on or about the handlebars. A cell phone photo will unlock the tether and permit the user to ride off. Knowing where other e-bike stations are is an important piece of the process. It will cost a dollar to unleash the bike and
20-cents-a-minute ($12 per hour) for usage, so it’s important to check it back in at another station at the end of a ride. If a renter has glitches on either end of the rental process, the app has answers.
Now that we have all of that squared away... climb aboard, grab a seat, fasten your seatbelt, make sure your tray tables are in the upright and locked position...and it's off to Indianapolis!
The flight lasts just shy of 2 hours in length so get comfy. We'll be landing at Indianapolis Intl. Airport where a rental car will take us into Irvington/Indianapolis.
Jay had booked a 2 bed suite for the four of us at the Hilton Garden Inn near the airport.
Using his Honors discount and choosing non-refundable, pay up front he got the suite for $370,47 for 2 nights, tax and fees included. Or $185.23 per couple. A far cry from $3500 per night in Salem.
We had a mini fridge and microwave, there was a restaurant on site, breakfast was included and there was an indoor pool. We had everything we wanted or needed and the hotel staff was marvelous. The room was clean and comfortable. What more can one ask for?
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October 23 - Friday
We got in late so I'm not counting this as a day in our itinerary.
Kendall met us and whisked us off for dinner on him at Vida, 601 E New York St, Indianapolis.
That was a culinary adventure I won't soon forget!
They offer a magnificent 7 Course Tasting Menu, each dish imbued with unique flavor combinations that showcased the chefs’ creativity.
The staff provided impeccable service, ensuring that each course was presented with care and professionalism.
Dinner at Vida's not just a meal; it’s a carefully curated experience that leaves you yearning for more.
Even if it is one of those squiggly plate fine dining establishments.
And hey...I got complimentary chocolate torte (which was out of this world) with "Happy Birthday" squiggled on it for my birthday so I'm not complaining!
After dinner Kendalll took us on a drive around Indianapolis to show us the Halloween decorations.
Those Hoosiers know how to do it up for Halloween! This was just one neighborhood Kendall showed us...
We felt like we'd walked onto the set of a Hallmark Halloween movie! These were Halloween decorations on steroids!
We could have driven around all night just looking at the decorations but we had work to do the next day...
October 24 - Saturday
The Indianapolis Halloween Festival Wellness Event (Wellness Fair) is held on Saturday, October 24, 2026, from 9:00 a.m. to 1:00 p.m. at Irvington Presbyterian Church, 55 Johnson Avenue, Indianapolis.
This free community wellness day offers a variety of health services.
Besides flu shots and screenings, you can access mental health services and learn about the prevention and treatment of a variety of conditions, such as stroke, diabetes, heart failure and others. You can also learn about wound care, maternity services, elder care, gun safety, nutrition, chiropractic care, dental care, and fire safety.
There were giveaways of bike helmets, smoke detectors, carbon monoxide detectors, fire blankets and first aid kits.
The Wellness Fair was a HUGE success, much to our delight.
Masquerade Ball
That evening we were invited to a Halloween Masked Masquerade Ball and if there's anything the four of us love it's any chance to dress up in costumes and par-tay!
Don your finest attire, conceal yourself behind a stunning mask, and join us for a night where candlelight flickers, music fills the air, and secrets hide behind every smile. This is a public event that is part of the Indianapolis Halloween Festival for you viewers in Indianapolis...
Dance beneath the glow of chandeliers, enjoy drinks and hors d'oeuvres, and immerse yourself in an evening designed for those who appreciate a touch of mystery. The mask is strongly encouraged. This is a 21+ event.
We had a ball at this event - no pun intended.
Event Details
Date: Saturday, October 24th
Time: 8-11 pm
Location: Irvington Lodge, 5515 E Washington St., Indianapolis.
Historic Hudson Valley Membership
Before we get into the Sleepy Hollow Halloween Festival, I want to mention the Historic Hudson Valley membership.because it saved us a considerable amount of money on the Festival events and shopping. For my birthday Jay got us a Senior Dual Membership. It cost $110 and you can easily spend that on just two Halloween events during the Festival.
Enjoy FREE or discounted tickets to our historic sites, The Great Jack O’Lantern Blaze, a wide range of events, and other exclusive perks. A Historic Hudson Valley membership offers unique experiences for everyone at a great value—it pays for itself with Blaze tickets and just one visit to a historic site! Your support helps fund our educational programs and ensure that these iconic Hudson Valley sites are accessible for generations to come.
They have several varieties of memberships at different price levels to choose from.
All members enjoy these benefits:
FREE TICKETS
Standard tours of Philipsburg Manor, Washington Irving’s Sunnyside, and Union Church of Pocantico Hills
The Pinkster Festival and Summer Saturdays at Philipsburg Manor
6 one-time use guest tickets for standard tours and select events (learn more)
Grounds passes for Washington Irving’s Sunnyside (May 8 – September 13)
DISCOUNTS
15% OFF tickets to Rip Van Winkle’s Journey, Legendary Tours of Washington Irving’s Sunnyside, Irving’s ‘Legend,’ Spirits of Sleepy Hollow Country, Twilight Village, Dickens’s Christmas Carol, and other special events
10% OFF shopping on site and online
EXCLUSIVES
Early access to tickets for our most popular events and tours, including The Great Jack O’Lantern Blaze, before they are available to the public
Members-only events and promotions
FREE ticket exchanges available by 5pm the day before your event or tour
We saved quite a bit using our membership so I wanted to bring it up as an option for you. And getting a jump on advance ticket sales is really helpful as most events sell out early!
Our friends Jonas and Lindsay at It's A Charming Life have done a couple of great (and very creative!) overview videos of Halloween in Sleepy Hollow... (Yes, all of that artwork at Bella's was done by Jonas! He's an immensely talented Swedish illustrator.)
Be sure to check out Jonas' and Lindsay's website (Lots of great stuff on there!) and their It's A Charming Life YouTube channel..
Tarrytown/Sleepy Hollow Halloween Parade
For those of you in New York and in the Tarrytown/Sleepy Hollow area, Saturday October 24th is also the date the Parade kicks off - if you don't want to miss it.
Parking in the Villages of Tarrytown and Sleepy Hollow will be extremely limited on the night of the Halloween Parade due to road closures. The Halloween Parade urges you to use Metro-North Railroad to Tarrytown Station or Westchester County buses instead.
We recommend getting to the parade route by at least 4 pm if you want to stake out a good viewing spot. You might also want to bring a lawn chair or camp stool to sit on if you don't want to stand during the entire parade.
Immediately following the parade there's a block party. We tried it one year but being shoulder-to-shoulder in a crowd and being jostled around every couple of minutes wasn't our idea of fun. We skipped the block party after that.
The block party crowd
October 25 - Saturday
Tip: Most restaurants in the Sleepy Hollow and Tarrytown area do not take reservations during the spooky season because crowds are too unpredictable.
It's to your benefit to book accommodations that include a complimentary breakfast with your stay. This eliminates the hassle for at least one meal per day of standing in long wait lines - particularly at downtown Sleepy Hollow and Tarrytown dining establishments.
For those that do take reservations, get your reservations in as early as possible.
Jay had booked us in at SpringHill Suites by Marriott Tarrytown Westchester County. (This is an all suite hotel.)
He booked a 2 bed suite for the four of us.
In the past, this hotel had terrible traveler reviews and deservedly so. It was a wreck in dire need of attention. However, within the past two years it has undergone a top-to-bottom complete renovation so is now very nice.
We had a microwave and mini fridge in the room, breakfast was included and there was a snack market if you wanted snacks. There were also several restaurants within 5-8 miles of the hotel. The cost split between us came to under $150 a night.
Everything was clean, comfortable and we did not find one thing that was in need of repair.
The four of us had just gotten new foldable E-bikes so we were anxious to try them out.
From Tarrytown, you can follow the Westchester RiverWalk along the Hudson River. This scenic route continues under the Tappan Zee Bridge and into Sleepy Hollow, but in some sections (e.g., from Kingsland to Rockwood Hall) you’ll need to walk or bike on streets on the portion of RiverWalk without sidewalks.
If you don't want to bike it, you can walk the RiverWalk and at an easy pace you can cover it in 25 to 30 minutes of walking. And there are plenty of benches to rest at along the way.
The RiverWalk is FREE for everyone to use.
Even if the weather is beautiful bring a sweater or jacket with you on the RiverWalk. When the wind whips up on the Hudson it can get chilly very quickly.
Walk For Wishes
Kingsland Point Park, 299 Palmer Avenue, Sleepy Hollow
- 9AM: Registration opens
- 10:30AM: Program begins
- 11AM: Walk begins
- Family fun continues until 2PM!
This family-friendly fundraiser brings together wish families, volunteers, sponsors, and the community to raise vital funds for children with critical illnesses - all set against the enchanting backdrop of Sleepy Hollow.
Enjoy a scenic stroll along the Hudson River’s River Walk, interactive photo ops, a legendary glass pumpkin patch, live music, food trucks, games, costume contests (pets included!), face painting, crafts, and more. Perfect for locals and visitors alike, the festival pairs perfectly with a visit to Sleepy Hollow’s famous haunts. Walk for Wishes is more than a fun fall day - it's a chance to make a difference.
Running in conjunction with this event is the Glass Pumpkin Patch, whose proceeds go to Walk for Wishes.
This festive event showcases hundreds of whimsical, vibrantly colored, blown glass pumpkins. These one-of-a-kind works of art will be available for purchase.
Proceeds support the Make-A-Wish® Hudson Valley Chapter.
The Headless Horseman Files
This was our first ticketed event and it runs from 10 am to 4:15 pm.
Four suspects, one missing schoolmaster, and 45 minutes to work out what happened — Sleepy Hollow’s whodunit, staged in broad daylight.
A guide walks you through the grounds of Philipsburg Manor, where the townsfolk of 1790 are waiting with their alibis. Fiery Hans Van Ripper, charming Katrina Van Tassel, spectral Hulda the Witch, and bold Brom Bones each have a story about the night Ichabod Crane disappeared — and each has a motive. You gather the clues and reach your own verdict.
Something is lurking in the shadows, too. The Headless Horseman doesn’t wait for nightfall here!
Recommended for ages 8+. One stretch takes place in near-darkness. Timed admission; advance tickets recommended.
We had so much fun at this event!
Afternoon: Lunch at Bridgeview Tavern & Beer Garden, 226 Beekman Ave Sleepy Hollow.
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A family owned and operated tavern & restaurant specializing in world class craft beer, house smoked bbq, prime beef & game burgers, regional American staples & tasty ethnic fare. A wide array of spirits, wine, sangria & seasonal specialty drinks are also available.
The vibe here was great, we sat in the beer garden in the back. Service was great. Our server made it a point to highlight weekly specials and made recommendations with enthusiasm.
Food was tasty and the only "complaint" (if you can even call it that) was water was served without ice and I had to hunt someone down to get a refill. No big deal.
Spirits of Sleepy Hollow Country
Held at Philipsburg Manor - 381 North Broadway, Sleepy Hollow
This is an absolutely fabulous magic show that sells out year after year, nearly the minute tickets go on sale.
Mark Clearview and Nick Wallace return to Philipsburg Manor this October with an original magic show built around the spirits of Sleepy Hollow Country — not generic stage spooks, but the local dead. Hulda of Bohemia, the healer the village called a witch. Major John André, the British spy caught just down the road in Tarrytown. And the Headless Horseman, who needs no introduction around Sleepy Hollow.
The premise is that none of them ever left, and all of them have something to say about it. What follows is an hour’s worth of illusion delivered with real comic timing — a magic show first, funnier more often than it is frightening, even as the lights drop and things begin happening that shouldn’t.
It runs about 50 minutes with no intermission, in reserved seats.
PREMIUM tickets include cabaret seating in the first two rows and complimentary beer or wine and a snack
Recommended for ages 10 and up. Expect dim lighting, moments of suspense, and effects designed to startle.
Evening: Dinner at Goosefeather, Tarrytown House Estate - 49 E Sunnyside Ln, Tarrytown, NY
Goosefeather brings an upscale, modern Cantonese and Asian-influenced menu to the Hudson Valley. Under Chef Dale Talde, the restaurant emphasizes innovation—using premium ingredients in dishes rooted in classic Cantonese techniques.
Its setting is also special: Goosefeather is housed in the historic King Mansion (part of Tarrytown House Estate), set above the Hudson with multiple dining rooms, gardens, fire pits, and lounge spaces.
Nor is it as expensive as you might think. You can order a specialty cocktail without second guessing yourself.
Expect elegant dim sum, dumplings, house-made noodles, refined barbecued meats, and fusion interpretations that push Cantonese cuisine into modern territory. The tasting menus or chef’s specials are especially recommended.
Twilight Village At Sleepy Hollow
Philipsburg Manor, Sleepy Hollow, NY
To cap off our Sunday night we'll visit Twilight Village at Sleepy Hollow.
This reminded me of a Washington Irving version of a Renaissance Faire with all of the booths. Twilight Village is an immersive outdoor experience with live storytellers, fire performers, and eerie encounters around every corner. Tarot readings (limited availability on a first-come, first-served basis). Pop-up market access with curious goods, oddities, and handmade wares. Food and drink including adult beverages available for purchase.
By far the hit of the night was the Headless Horseman - although people seemed more interested in petting his horse than paying much attention to him.
Plan on spending 45 minutes to 1 hour to go through Twilight Village.
October 26 Monday
Morning: Breakfast at your accommodations.
We're going to bike down the Riverwalk again today to get where we're headed...but if you want to walk or take the Line 13 bus you can do that too.
You can ride the Line 13 Bee-Line bus directly from Tarrytown Railroad Station to the Sleepy Hollow Riverwalk area.
On weekdays during Halloween both Tarrytown and Sleepy Hollow tend to roll up their sidewalks as far as Halloween events go...so we'll hit some spots that don't have events.
Sleepy Hollow Cemetery
540 North Broadway, Sleepy Hollow
To get to the cemetery from the RiverWalk:
Head east toward North Broadway, following local streets and sidewalks. The walk is approximately 0.4 miles and takes around 10 minutes depending on pace and traffic.
While you can take guided tours of the cemetery if you wish, I'll save you the tour fee and you'll get the same information you'd get on the guided tour.
Go to the cemetery office (540 North Broadway, Sleepy Hollow) and pick up an 8.5" x 11" map of the cemetery. The office has a literature box where you can get free legal-sized (8.5x11) maps for self-guided tours to major features.
Better yet, purchase a 17"x20" map from Headless Horseman Gifts (Sleepy Hollow Gifts) showing over 50 special features of the cemetery. Around $8 USD plus shipping.
For a quick, self-guided visit, the free map is ideal; for a more comprehensive view, buy the full-color version. (Trust us, buy the $8 version and save yourself a tour cost!)
However, if you want to take a guided tour, there are 2 that are offered.
There's a daylight tour and a night tour by lantern light.
Advance tickets are required. Tickets can be scanned off your mobile phone if you are unable to print them out.
Daytime tours
Night time lantern tour
Daylight tours run Saturdays and Sundays from 2:00 - 4:00 p.m. through Thanksgiving weekend. In October also 10:00 a.m. - 12 noon.
Night time tours run In October daily 7:00 - 9:00 p.m., also 10 p.m. - 12 midnight on weekends through November 8th. Saturday nights through Thanksgiving weekend from 7:00 - 9:00 p.m.
There's also a Murder & Mayhem Tour for those 18 years+.
The true stories on this two-hour lantern tour are so grim, you just might have nightmares!
Curious to learn about a family that lost 5 children one terrible afternoon, or a horrific murder that led police on a multi-state chase? Maybe you’d like to hear about a son who shot his father before turning the gun on himself, and a daughter who poisoned her mother? If so, then this is the tour for you!
Every Saturday night through Thanksgiving weekend. Thursday nights from September 24th through November 12th. Check individual dates for start times.
Of course, the most notable person buried in the cemetery is Washington Irving himself. Just look for the black wrought iron gate that says IRVING on it.
This cemetery can be eerie. While we were looking at Washington Irving's grave this huge black crow the size of an A30 Airbus landed nearby and just stared us down. ???
The Old Dutch Church & Burial Ground
The Old Dutch Church and Burying Grounds are the ones famously featured in “The Legend of Sleepy Hollow”. The Old Dutch Church is also one of the oldest churches in the state. The church is still active today, and outside of October is rarely open for visitation by the public.
The interior of the church is kind of beautiful in its simplicity. And it's the only church I've ever seen with a woodburning stove in it!
Its burial grounds contain graves from the 1600's.
In the month of October the church offers live readings/shows of “The Legend of Sleepy Hollow” with tours of the church and burying grounds. Year-round you can walk the grounds outside of the church and burying grounds.
Headless Horseman Bridge
What people take for the Headless Horseman Bridge isn't the real Headless Horseman Bridge. The actual location of the Headless Horseman Bridge is now a modern bridge.
The real Headless Horseman Bridge rotten away ages ago.
About a half-mile upstream from where the bridge that played a role in the writing of Irving’s story sits the small, wooden bridge crossing the Pocantico River.
It's within the Sleepy Hollow Cemetery.
Afternoon: Lunch at Beekman Ale House, 92 Beekman Ave Sleepy Hollow.
I'm not sure which I enjoyed more - the pizza or the window decorations.
A young waiter at another restaurant actually recommended Beekman's to us. Said it was the best pizza he ever ate.
Well, it's pretty tough to please someone who comes from the Best Pizza Ever areas...but he was right!
It was darned good pizza. We had the French Onion variety - caramelized onions, parsley and gruyere cheese.
I'd love to know how they get the crust as thin as they do without the pizza flopping all over the place. We polished off the first pizza in what I'm reasonably certain was Guiness Book of Records world breaking time - and then ordered a second pie.
Beekman's is a local hang out and it's easy to see why. Thumbs up from us!
Headless Horseman Statue
Sitting in the center of Sleepy Hollow is the Headless Horseman Statue. You will need to be careful with this stop as it sits in the center of a busy highway. The 18 foot tall statue represents the Headless Horseman chasing Ichabod Crane. It was designed by local artist Linda Perlmutter and revealed in 2006.
It is only a couple minutes walk from the Old Dutch Burying Ground, so after visiting the site of the original Headless Horseman bridge, continue and you will shortly find the statue.
Stroll Through Sleepy Hollow Downtown District
Sleepy Hollow is one of the most unique small towns in New York’s Hudson Valley, blending American history, literary significance, beautiful scenery, and seasonal festivities into one memorable destination. While many travelers initially visit because of The Legend of Sleepy Hollow, they often leave surprised by how much there is to see beyond the famous ghost story.
The village offers something for nearly every type of traveler. History lovers can explore centuries-old landmarks and historic estates, outdoor enthusiasts can enjoy scenic riverfront walks and parks, and families will find plenty of seasonal events during the fall.
We mainly wanted to see the Halloween decorations but found some unique shops too:
Cozy Coven, 31 Beekman Avenue, Sleepy Hollow, NY, 914-505-6574 Serving up a curated selection of mystical gifts, home décor, and metaphysical supplies. Their products include tarot cards, crystals, candles, books, and gemstone jewelry, catering to those seeking spiritual development and healing.
Headless Horseman Gifts, The ‘home of all things headless’ carries unique and hard to find items with, naturally, an emphasis on Sleepy Hollow’s own headless horseman. T-shirts, sweatshirts, hoodies, hats, pewter and glass ornaments, key chains, magnets, coffee mugs, shot glasses, bumper stickers and decals, books and maps. Always available online, and on weekends you might find their table set up outside the south gate to Sleepy Hollow Cemetery.
Sleepy Hollow Bookshop, 95 Beekman Avenue, Sleepy Hollow, NY. Along with the wide selection of books focusing on children and young adults, they have Sleepy Hollow souvenirs for all ages. From adult and children's editions of “The Legend of Sleepy Hollow" to tote bags, ornaments and more, take a little bit of Sleepy Hollow wherever you go. Whatever you do, don't lose your head in all of their spooky stories and terrifying tales for all ages.
Evening: Dinner at Bistro 12, 12 Main St, Tarrytown.
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Bistro 12 offers Mediterranean fare featuring dishes as varied as northern Italian fettuccine Bolognese, a French braised rabbit in a demi-glace, the traditional Portuguese Alentejana - pork with clams and potatoes in wine sauce - and even a Greek specialty: grilled octopus on a bed of delicately flavored escarole.
The freshest fish specials, Red Snapper, or fillet of branzino in a lemon/wine reduction, provide a healthy dinner especially when
accompanied by Bistro 12's delicious side dishes of fresh spinach or escarole.
All desserts are made in house: homemade caramel custard, tiramisu, chocolate mousse or the molotoff (meringue). Lemon tarte, a sweet crust enveloping a tart, lemony filling.
This is one of my favorite restaurants we dined at during our trip. Everything was A+ from food to service to atmosphere.
The Great Jack O'Lantern Blaze
More than 7,000 hand-carved jack o’lanterns light up the riverside grounds of Van Cortlandt Manor.
Ten acres of an 18th-century estate above the Hudson become a half-mile walk past life-sized dinosaurs, a working carousel, a planetarium built entirely of glowing gourds, and the Headless Horseman riding out of the dark.
Arches, tunnels, and clearings open up where the pumpkins climb well above head height, all of it lit in sequence and scored to an original soundtrack, so the light moves with the music and the walk keeps reintroducing itself around each bend.
Spooky, not scary. No jump scares, no actors chasing you — it works as well for a six-year-old as for the friend who claims they’ve outgrown Halloween.
Two ticketed add-ons let you step off the trail midway: the Gourd & Goblet Tavern, inside the manor’s 18th-century brick tavern, and the Headless Horseman’s Hideaway, a pop-up lounge with visits from the Horseman himself. Both must be booked in advance.
Advance tickets only — nothing is sold at the gate, and dates sell out. FLEX tickets get you in on any open night, even when the calendar is full
October 27 Tuesday
Morning: Tired of the hotel breakfast and the guys were craving bagels so we hit up Horseman Bagels, 276 N Broadway, Sleepy Hollow.
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Service was slow (1 woman doing 3 jobs) but the bagels were good. There's not much seating inside, but they also have some seating outside.
There were no Halloween events going on anywhere so we decided to make this an R&R day on the itinerary. You can do the same and do whatever you feel like doing. It's an R&R day!
We decided to make our own Halloween event for the day.
Pop on over to Sleepy Hollow to The Village Confectionery.
Scoop up all the Halloween treats you can carry - caramel apples, Halloween popcorn, candy, apple cider, etc.
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We put on our jammies, laid on our beds and livestreamed some Halloween movies, starting with the Tim Burton/Johnny Depp version of Dark Shadows. If you've never seen it, it's hilarious. A sneak preview...
Yes, Depp also starred as Ichabod Crane in the movie The Legend of Sleepy Hollow - which we also watched.
50 Greatest Halloween Movies of All-Time
Evening: Dinner at J.P. Doyle's Restaurant & Public House, 48 Beekman Ave, Sleepy Hollow.
Tacos? Trivia Night? A pub owner that dresses like this?
COUNT US IN!
We had such a good time we closed the bar!
And the Halloween decorations in the pub were fantastic.
Thank you Aerik Von for a wonderfully entertaining evening!
October 28 Wednesday
Today we're going to visit nearby Irvington, NY - 2.8 miles or 8 minutes from Tarrytown.
Morning: We had some time to kill before the first scheduled event so decided to have an upscale breakfast at Red Hat On the River, 1 Bridge St. Ste 150, Irvington.
Red Hat on the River is a popular spot known for fast-moving lines, streamlined ordering, solid value for money, consistent flavor across the menu, a relaxed ambience, fresh flavors, friendly staff, easy access and a place locals mention to friends.
Heads up: street parking may be your best bet and reservations may help.
Myths & Mysteries of The Octagon House
45 West Clinton Avenue, Irvington
The Armour-Stiner Octagon House is the biggest visitor draw in Irvington. This is definitely a house you want to take a guided tour of!
The Armour-Stiner Octagon House has long been the subject of local lore, its rooms holding stories that go well beyond the ordinary house tour. From September 25 through November 2, 2026, Myths & Mysteries invites visitors into the enigmatic tales and personal accounts of the house’s past residents, uncovering the secrets held within its walls. Expect narratives where the living and the ethereal sit close together, and come away with a deeper appreciation for just how strange and storied this house really is. (It is haunted by the Lady In White ghost)
At the conclusion of the tour, visitors are invited to experience Remember You Must Die, a curated exhibition from the Memento Mori collection of Ryan Matthew Cohn featuring objects ranging from ancient artifacts to contemporary works and examining the ways past generations confronted mortality through art, ritual, memory, and spirituality.
Ages 12 and up only, please.
The tour lasts about an hour.
They have limited restroom facilities, so we recommend planning ahead and using the restroom before arriving at The Octagon House. Especially during busy times, their restroom may be unavailable prior to the start of your tour.
Read their website for their other restrictions before taking this tour!
There are a couple of other Halloween tours you can take at Octagon House...
Tis the Wind and Nothing More
tour
The Lady In White tour
Take A Selfie With Rip Van Winkle
90 Main St, Irvington
As you travel about downtown Irvington you'll undoubtedly see the Van Winkle Statue on Main Street.
This was created in 2002 by Richard Masloski. It is a Bronze statue that captures the character created by Washington Irving.
"Rip Van Winkle depicts the literary character reclining. He has a large beard and crumpled hat and his eyes are half-open as if he has just woken up. His boots and hands blend in with the ground like he has become part of the ground.
It is located on Irvington's Main Street under a beech tree between Town Hall and the Main Street School.
Tour Sunnyside
3 W Sunnyside Ln, Irvington
Nestled along the banks of the Hudson River, the landscape of Washington Irving’s much-loved Sunnyside has been charming guests for generations. Visitors today hear about Washington Irving’s storied past and how he came to be America’s first internationally famous author. His characters, from the Headless Horseman to Rip Van Winkle, are global icons, and Irving’s legacy lives on at his whimsical estate.
Washington Irving purchased the property that became Sunnyside in 1835 for $1800. The estate, located on the Hudson River at the border of Tarrytown and Irvington (now in Irvington, NY), was an 18th‑century farmhouse known as “Wolfert’s Roost” before Irving’s acquisition.
Irving lived at Sunnyside for the remainder of his life, except for a four‑year period when he served as U.S. ambassador to Spain. He died in 1859 at the age of 76, and Sunnyside remained in the Irving family until 1945.
The items in the house you'll see on your tour actually belonged to Washington Irving and/or came from his family.
That last photo on the slideshow above that looks like a chapel was the icehouse.
Tour guides dress in period costumes which is a fun touch. A lot of the items in the house are directly from Irving or his descendants, so it was very informative to learn about his life and his most well-known books. The house has a nice view of the river and makes for a nice walk around the property after when the weather is nice.
There is a big parking lot then a short trek to the visitor center.
Visitors Center
There's also a nice gift shop you can peruse while you wait for your tour to begin.
Gift shop
Aside from visiting and touring the house, you can also enjoy walking the trails on the grounds surrounding the home. The grounds feature paved walking trails, colorful gardens, and open lawns. Interpretive signs can also be found around the property, highlighting the history of the area.
Timed tours are offered daily during the warmer months and, like many other locations in Sleepy Hollow, Sunnyside offers special Halloween themed events in the month of October.
The main Halloween event at Washington Irving’s Sunnyside is “Irving’s Legend,” a live outdoor storytelling of The Legend of Sleepy Hollow with live music, sound effects, and costumed performers, running through late October.
Daytime Self Guided Legendary Tour:
Irvington's Legend:
By the way...this is a fantastic place for a picnic lunch if the weather is cooperating.
Before your tour stop at Geordanes Neighborhood Market.
57 Main Street, Irvington.
Geordane's has everything you need for a great picnic - readymade!
Yes, the Sunnyside staff will allow you to picnic on the grounds as long as you clean up after yourself and leave no trace. The views of the Hudson from the Sunnyside estate are magnificent!
And if you're not in the mood for a picnic, then have lunch at Geordane's anyway. Their food is really good and you'll save yourself a few bucks on dining out.
Take A Stroll Through Hudson Park
29 Bridge St, Irvington
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The park includes two regulation ballfields overlain by a regulation soccer field.
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There are two playground areas for young children.
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Nearly one-mile of pathways that weave around and through the site.
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There are approximately 4.5 acres of open lawns for passive recreation, picnicking and appreciating views of the Hudson Highlands and Hudson River.
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A senior citizens’ center created in the renovated industrial office building.
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There are 74 parking spaces.
There’s no better way to cool off after a long day of exploring Irvington than with a picturesque walk beside the Hudson at Scenic Hudson Park. The space is open until 10 p.m. through November 30, so there’s no time like the present to take in the natural sights and sounds of the river.
Evening: Dinner at Hudson Prime Steakhouse, 5 N Buckhout St, Irvington.
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Full service steakhouse serving prime dry aged steaks and seafood.
What an unforgettable experience! We dined in a private room near the entrance, and from start to finish, the service felt truly top-notch and luxurious.
Every dish we tried was delicious! The drinks, ambiance, staff, owner, and overall environment all came together to create such a memorable experience. Everyone made us feel welcomed and celebrated.
I even got a complimentary dessert for my birthday.
Mon Closed
Tue 4:00 PM - 10:00 PM
Wed 4:00 PM - 10:00 PM
Thu 4:00 PM - 10:00 PM
Fri 4:00 PM - 10:00 PM
Sat 4:00 PM - 10:00 PM
Sun 4:00 PM - 10:00 PM
October 29 - Thursday
Morning: Breakfast at your accommodations.
Union Church of Pocantico Hills
We had free tour tickets so decided to pay Union Church a visit.
Stained-glass windows by European masters, commissioned by the Rockefeller family, adorn this unassuming country church. Henri Matisse’s last commissioned work, the Rose Window, and nine windows by Marc Chagall create
a dramatic combination of light and color, art and spirituality.
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It's a relatively simple church but the stained glass windows are magnificent. Take a virtual tour of them here.
The themes of the Chagall windows are The Good Samaritan, The Crucifixion, Joel, Elijah, Daniel, Cherubim, Ezekial, Jeremiah, and Isaiah.
Union Church of Pocantico Hills is a small, country church tucked away in the hills above Sleepy Hollow. The non-denominational Protestant congregation was founded in 1915. Its present building was constructed in 1922 on land donated by John D. Rockefeller, Sr.
Tours are conducted by Historic Hudson Valley, which also operates Washington Irving's Sunnyside, Philipsburg Manor, and Van Cortlandt Manor.
Visits start with a brief history from a Historic Hudson Valley museum educator, followed by time to explore the church at your own pace. Most visitors spend 30–45 minutes on site.
Street parking or in the small lot next to the church.
Timed tickets are $12; free for Historic Hudson Valley members. Tickets are not sold on site — purchase in advance online or at the Philipsburg Manor Visitor Center.
Philipsburg Manor
381 N Broadway, Sleepy Hollow
You've already attended some events here but they don't give you a tour of the mansion or tell you the story of it.
The Phillipsburg Manor is a 1750 English manor that once housed African slaves. The Manor is a restored 18th-century farm and trading center that sits along the Pocantico River and offers interactive exhibits, historic buildings, and beautiful grounds to explore.
Learn about the enslaved individuals who worked on the property in the year 1750, and whose family relationships and personal histories are revealed in primary documents.
Step into the gristmill and learn about the life of Caesar, the enslaved miller, whose unmatched expertise contributed to the wealth of the Philipse family but benefited him not at all.
Visit the dairy in the cellar of the Manor House, where a commercial butter production was operated by Dina, Massey and Sue, three of the women enslaved by the Philipses at the site.
Costumed interpreters offer demonstrations of traditional crafts, farming techniques, and daily activities that would have taken place more than 250 years ago.For families who love being outdoors, you can stroll along the scenic pathways, watch the water-powered gristmill in action, and enjoy views of the river and surrounding landscape.
During the summer, special events take place on Saturdays with family-friendly activities, music, dancing, and storytelling. In October the manor transforms into a haunted house-Headless Horseman Hollow.
Afternoon: Lunch at Santorini Greek Restaurant, 175 Valley St, Sleepy Hollow.
Santorini Greek Restaurant offers a modest yet vibrant setting where guests can enjoy classic Greek dishes along with live music and belly dancing on Saturdays.
This family-friendly restaurant has been highly praised by The New York Times for its exceptional Mediterranean cuisine. The menu features a variety of healthy and vegetarian options, as well as soft foods suitable for all ages.
Take A Hike In Rockefeller State Park Preserve
Rockefeller State Park Preserve, Route 117, 1 mile east of Route 9, Sleepy Hollow, NY 10591. This park spans over 1,700 acres donated by the Rockefeller family, laced with roughly 55 miles of crushed-stone carriage roads originally laid out by John D. Rockefeller, Sr. and Jr. Seasonal activities include hiking, recreational running, bird watching, fishing (New York State fishing license and Rockefeller Park permit required), picnicking, horseback riding, carriage driving, photography, painting, and
geocaching (park permit required). In winter, there are sledding hills, snowshoe trails, and cross-country skiing. Household pets are allowed on leash.
There's a $6 parking fee for car parking in the lot at the main entrance (free for holders of Empire Pass). Trail maps are available at the park visitor center and through Friends of the Rockefeller State Park Preserve. The park map is also available as a printable PDF here. Preserve grounds are open year round, sunrise to sunset. The office is open 9 am to 4:30 pm.
Evening:
Masque of the Red Death at Lyndhurst
In October, Lyndhurst Mansion transforms into Prince Prospero’s abbey for an immersive theater experience drawn from Edgar Allan Poe’s The Masque of the Red Death. As a guest of Prospero, you’ll move through the Gothic halls of the 1842 mansion — dressed in the garish colors and grotesque beauty of Poe’s tale — walking room to room with delight and dread as the story of the doomed revelers unfolds around you.
Performed and produced by the Irvington Shakespeare Company, this feverish masquerade unfolds over an evening inside one of the Hudson Valley’s great Gothic Revival houses — a fitting stage for Poe, and a perfect one for Halloween.
An immersive, walk-through experience involving long periods of standing and stairs; the mansion has no elevator.
Arrive 15 minutes early; check in at the Welcome Center (accessible restroom available).
Recommended for ages 12 and up.
Lyndhurst is an exquisitely beautiful mansion, built as a country manor in 1838. The next owner added a grander dining room, more bedrooms and a tower in 1864.
After the tour we were then on our own to walk the grounds and visit the bowling alley building.
This event is scheduled every 20 minutes during the evening.
Late dinner: Ambar, 194 Beekman Ave, Tarrytown.
We'd never really gotten into trying Dominican food before so decided to try Ambar.
Wow! The sautéedchicken, steak and shrimp was phenomenal.
Jay ordered the pernil, Jude the sautéed steak strips with white rice and beans, and Dee ordered the garlic shrimp.
They said their food was as equally as good as my own was.
The people there were super friendly and accommodating.
The portions are BIG for a very reasonable price.
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October 30 Friday
Morning: Breakfast at your accommodations.
OR one of the staff at the hotel recommended the Breakfast & Burger Club, 84 Main St., Nyack, NY.
Nyack is 8.5 miles from Sleepy Hollow.
It didn't disappoint on any front!
This little gem captures your attention with prompt, friendly service and some unique twists on traditional breakfast fare. Although they offer the traditional fare as well.
Reasonable prices too.
Chicken & Waffles
Cookies & Cream Pancakes
Chocolate Bliss Waffle
There were no events taking place until 3 pm so we brought our bikes along and rode the trails in Rockland Lake State Park.
Rockland Lake State Park offers a mix of paved, scenic, and connected bike paths, including a 3‑mile lake‑side loop and longer regional routes, all accessible year‑round from daylight to dusk.
Rockland Lake State Park Bike Path – A 3‑mile, flat, paved loop around the lake, starting near Congers Lake Memorial Park or Parking Field 6. Easy; suitable for all fitness levels. Fully paved, tree‑lined, passing picnic areas, open fields, and recreation zones.
From I‑87/287, exit 12 to Route 303, then follow signs to Congers Lake Memorial Park or Parking Field 6 (parking fee applies)
An Audience With Poe
Historic Hudson Valley - 639 Bedford Road, Tarrytown
Professional storytellers bring to life the “powerful graphic effect” that Washington Irving once praised in Edgar Allan Poe’s writing, with haunting renditions of The Raven, The Tell-Tale Heart, The Black Cat, and The Masque of the Red Death. We pair the tales with complimentary cocktails or mocktails designed to capture the spirit of the stories.
The evening begins in the Library at Historic Hudson Valley, where visitors enjoy their first drink while standing among the shelves, listening to a creepy tale. From there, the experience deepens in an intimate theater setting, with three more of Poe’s dark masterpieces performed in turn, as those gathered sip drinks and enjoy small treats—indulgences to savor in the night’s shadows.
Just my personal opinion here...but I think you'll get the most out of this event if you're a fan of the works of Edgar Allan Poe. I am so I enjoyed this event...but someone who doesn't care for Poe might not enjoy it.
RECOMMENDED FOR AGES 16+
Advance Tickets Only. Not Sold on Site.
Evening: Have dinner at the restaurant of your choice. We returned to the hotel and had dinner there.
The Legend of Sleepy Hollow and Local Lore
Rockwood Hall, Phelps Way, Pleasantville, NY
You set off along a lamplit path toward the foundations of Rockwood Hall, the vanished William Rockefeller mansion whose grounds were laid out by Frederick Law Olmsted — the same hand that shaped Central Park. What remains is a stone terrace on a bluff, with the Hudson below, the Tappan Zee Bridge to the south, and on a clear night the Manhattan skyline beyond it.
It is, in daylight, one of the most beautiful places in Westchester. After dark, with a lantern and a storyteller, it becomes something else.
The program moves from the Preserve’s own lesser-known lore into “The Legend of Sleepy Hollow” itself — and to the real places behind it, most of which are within a few miles of where you’re standing. Then the evening closes the way it has to: with the Headless Horseman, mounted, coming out of the dark.
The evening is performed by David Neilsen, a Tarrytown-based author and storyteller who has spent years telling this story on the ground that produced it — at Sleepy Hollow Cemetery, at Washington Irving’s Sunnyside, and at the Poe Cottage, along with the New York Botanical Garden and the Hudson River Museum.
His Legend isn’t a recitation. He performs the tale and then opens up the history beneath it: the real people, the real places, and how much of what Irving wrote came out of a few square miles of this valley. He also performs a one-man show as Major John André, the British spy captured up the road in Tarrytown — which is to say the local dead are his regular company.
It’s a walk, in the dark, on park paths. Wear proper shoes and dress for a night by the river in late October. The event begins at 6 pm.
Finding the entrance
Worth reading twice, because this catches people out. Rockefeller State Park Preserve has two separate sections divided by Route 9. The main entrance, visitor center, and Preserve office are at 125 Phelps Way, off Route 117 — and that is not where this event takes place. Rockwood Hall is the western section, reached from Route 9 (Broadway) closer to the river, with its own separate access and parking.
If you’ve only ever visited Swan Lake and the carriage roads, you have not been to Rockwood Hall. Allow extra time, and confirm the meeting point with the Preserve before setting out in the dark.
Preserve information: parks.ny.gov or 914-631-1470
October 31 Saturday
HALLOWEEN!
Morning: Last day in Sleepy Hollow so treat yourself to breakfast out at the restaurant of your choice.
Dark Shadows
Most of you are probably too young to remember the 1966 TV show, Dark Shadows.
It was a Gothic soap opera about a vampire named Barnabas Collins.
It became so popular that it turned into a cult classic.
In the spin off movies House of Dark Shadows (1970) and Night of Dark Shadows (1971), the Lyndhurst Manor served as
Dark Shadow's'Collinswood Manor'! You can read an account of filming both movies at Lyndhurst here.
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So it's only fitting that Lyndhurst's Halloween event is an all day affair centered around Dark Shadows. It's an all-day costume party with three different ways to experience Lyndhurst as Collinwood – including a Meet & Greet with Kathryn Leigh Scott and other Dark Shadows stars.
You’ve seen the mansion and the movies, but have you seen all the hidden areas
of the estate where Dark Shadows was filmed?
The Dark Shadows Walking Tour of the property will explore the grounds for about an hour and visit some of the iconic exterior locations from both Dark Shadows films shot here at Lyndhurst. This tour will take place outdoors on uneven ground and involves a lot of walking, so wear comfortable shoes. As this tour takes place outdoors, come prepared for the weather. In the event of inclement weather, the tour will occur in the Welcome Center as a media presentation/lecture instead.
Please be advised that this tour requires long periods of standing and walking.
Please arrive 15 minutes before the entry time on your ticket. If you are late, they will do their best to accommodate you, but they cannot guarantee it. You check in for the tour at the Welcome Center. Not recommended for children under 8 years of age.
Afternoon: Lunch at DeCicco & Sons, 1 Legend Drive, Sleepy Hollow
Trust me when I say you haven't seen a grocery store like this. This warehouse-like space, with two floors, offers aisles of fresh, canned and prepared foods but the piece d' resistance is the second floor bar and outdoor patio where The Hollows pub serves smash burgers, pizzas, sandwiches and more.
Also special: memorabilia from the 1999 film "Sleepy Hollow" including costumes the Headless Horseman (as worn by Christopher Walken and his stunt man Ray Park) wore. You'll also see displays of the Lady Van Tassel dress worn by Miranda Richardson and a Hessian Soldier outfit.
Costumes from the 1999 film "Sleepy Hollow" are on display at DiCicco's.
Photo credit: Enormous Creative
In addition, there's a wall full of concept art from the Disney animated version of "Sleepy Hollow" painted by Mary Blair.
Other spooky touches include the bar’s beer tap with a silhouette of the Headless Horseman and a Headless Horseman purse holder under the bar.
Evening: 5pm to 6:30pm
Small Bites At Collinwood
Close out Halloween night with the most devoted Dark Shadows fans at an intimate evening gathering inside Collinwood itself. Mingle with actress Kathryn Leigh Scott and special guests over drinks and hors d’oeuvres on the veranda, then wander the first, second, and kitchen levels of the mansion. The tower — open only during this special evening — is yours to explore.
Come in your best Dark Shadows cosplay or Halloween costume for a chance to win a prize. Every ticket includes a Dark Shadows souvenir.
Ages 21 and older only. Involves long periods of standing and flights of stairs; restrooms are down stairs on the basement level.