Since our usual Halloween trip wasn't in the cards for us this year, I thought I'd bring you a previous Halloween trip we took to Indianapolis, IN and Sleepy Hollow, NY. As far as we're concerned there are no two better places to be in on Halloween. You can keep Salem's $3500 per night hotel rooms!
This was going to be a bit of a "working" vacation for us in that when we travel, we try to fit in some volunteer work or even center our trip around some volunteer work and this was the case with this Halloween trip. It was a combination working trip and birthday present from Jay.
So that you don't get confused...there are two Irvington's we'll be visiting - one in Indiana, one in New York's Hudson Valley.
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The Back Story
Jay and his brother, Jude have a doctor friend in Indianapolis that regularly volunteers at the Irvington, Indiana Halloween Wellness Fair. He (Kendall) asked Jay and Jude to volunteer at it and they were only too happy to do so.
Jay and Jude also volunteer a lot of time to Make A Wish Foundation for critically ill children, that sponsors a fundraiser in the Irvington, New York Halloween Festival.
Jay had already planned this Halloween trip for my birthday when Kendall asked them to volunteer and visit him in Indianapolis.
Jay was in a tizzy...now what should he do?
I told him "Let's just combine both and Dee and I will volunteer too in whatever capacity we can. We can do everything in one trip."
So that's what we did.
We flew into Indianapolis Intl. Airport, which is about 7 miles southwest of downtown Indianapolis and rented a car.
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.
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We arrived in Indianapolis later in the day so I'm not counting this as a day of the 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.
The people of Indianapolis know how to decorate for Halloween!
This was just one neighborhood!
It was a Halloween decoration feast for the eyes! We didn't know where to look first to take it all in! It was in a word, "enchanting".
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, including:
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Flu vaccinations
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A blood drive
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HIV testing
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Fasting blood sugar testing & diabetes support
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Drug take-back
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Mental health support
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Dental
and much more!
October 24 Saturday
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 so 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: 8-11pm
Location: Irvington Lodge, 5515 E Washington St., Indianapolis.
Tarrytown Halloween Parade
For those in Sleepy Hollow/Tarrytown you don't want to miss the Tarrytown Halloween Parade.
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.
You want to get to the parade route at least 1 hour ahead of the 5 pm kickoff to stake out a good viewing sport. You might also want to consider bringing a lawn chair or camp stool if you don't want to stand the entire time.
Immediately following the parade there's a block party. If you can handle being shoulder-to-shoulder and being jostled around in a huge crowd, by all means go for it.
The block party crowd
October 25 Sunday
A couple of things to know about Tarrytown and Sleepy Hollow...
At one time they were both the same village, until Tarrytown split off to be its own village.
However, the two are adjacent to one another and are so close you can walk between the two of them.
Secondly, there are no accommodations in the village of Sleepy Hollow. They are located in Tarrytown.
Both villages get absolutely MOBBED during Halloween. A trip to their Halloween festival needs to be planned at least 8 months in advance if not more as everything books up.
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.
The hotel had just undergone a complete renovation so was very nice - and comfortable. 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.
Tip: Most of the restaurants in Tarrytown/Sleepy Hollow don't take reservations during spooky season so it's to your benefit to book accommodations that at the least, offer complimentary breakfast. That takes out one meal of the day you won't have to battle crowds and long wait times for a table. Also, try to avoid the downtown area restaurants as they get the busiest with the longest lines.
Jay had gotten us foldable E-bikes for my birthday so we were anxious to try them out.
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.
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.
The RiverWalk is a beautiful walk or bike ride. At a comfortable walking speed of around 3 miles per hour, you can expect to cover it in roughly 25–30 minutes for a leisurely stroll.
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.
Glass Pumpkin
Patch
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.
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.
The glass pumpkins are beautiful. We bought several of them.
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.
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 biggie at all.
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 tours
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
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.
Visit Downtown Tarrytown
Scarecrows lining a fence in downtown Tarrytown
Again we were mostly scoping out the Halloween decorations but stopped in a couple of shops:
Trilogy Consignment, 54 Main Street, Tarrytown, NY, 914-631-3426. Modern and vintage styles for women and men, jewelry, and unique artisan objects including locally designed t-shirts sourced and printed in the USA.
Transom Bookshop, 23 Main Street, Tarrytown, NY. Transom carries a wide selection of Washington Irving books, including a variety of editions of The Legend of Sleepy Hollow, plus Headless Horseman souvenirs, Halloween-themed gifts, and books by local authors.
The Purple Ostrich, 7A S Broadway, Tarrytown, NY, 914-418-5417. Tarrytown's newest gift shop has everything from souvenirs to socks, sunglasses to puzzles, as well as stickers and greeting cards. So many fun items that are just too hard to put in a category! The eclectic treasure trove includes Sleepy Hollow & Tarrytown T-shirts, magnets, stickers, mugs, shot glasses, totes, and postcards.
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