October Unleashed: The Ultimate Guide to Fall Festivals, Haunts & Happenings in New York
- Hudson Valley Happenings
- Oct 1
- 30 min read
Updated: Oct 3
October doesn’t tiptoe into New York — it barrels in with a calendar so stacked, you’ll wonder how to fit it all in. This is the month when haunted houses stretch longer, festivals blaze brighter, concerts hit harder, and every corner of the Hudson Valley and beyond feels electric with fall energy. It’s not just the peak of spooky season — it’s the peak of everything.
We're so ready for witches paddling the Hudson in full costume, 70,000 pumpkins glowing at once, ski jumpers soaring against Adirondack foliage, indie bands and muralists transforming Kingston, and world-class riders leaping fences by day before the arena turns into a rock concert by night. Add in Oktoberfest steins, farm dinners that double as fantasy banquets, and haunted attractions so massive they’ve broken world records — October is unapologetically extra.
This guide is your cheat sheet to making the most of it. We’ve scouted the festivals, hand-picked the foodie experiences, and highlighted the concerts, scares, and family traditions that define fall in New York. Each one has its own vibe, its own magic, and its own reason you’ll regret skipping it.
So grab your crew, block your weekends, and get ready to dive headfirst into autumn’s wildest stretch. Here’s everything you need to make October 2025 unforgettable.
Quick Reference Directory
Oct 1-Nov 16 • The Great Jack O’Lantern Blaze Oct 11 • Cirque Du Creep: Fright Night at The Yard
Oct 1-Nov 2 • Pure Terror Scream Park Oct 12 • SUP Witches of Sleepy Hollow Festival
Oct 1-Nov 1 • Headless Horsemen. Oct 12 • Bridlemont Concours Car Show
Oct 4–Nov 2 • Dogwood Acres Pumpkin Party Oct 10–12 • O+ Festival Kingston
Oct 1–5 • Silo Ridge Masters Oct 17 • Harvest & Half Moon Dinner Series Kickoff
Oct 8–12 • Highlands Cup Oct 18–19 • Spellbound Festival
Oct 10 - Nov 1 • Scared by the Sound Oct 18 • Adirondack Brewery Oktoberfest
Oct 10 • Third Eye Blind & Dinosaur Jr. Concert. Oct 19 • Greystone Wine Tasting & Auction
Oct 11–12 • Flaming Leaves Festival Oct 18 • HV Craft Beer & Food Truck Festival
Oct 11 • Brothers Osborne & LeAnn Rimes Concert. Oct 26 • Fall Harvest Festival at Fishkill Farms
Oct 10–Nov 2 • Peace, Love & Pumpkins Oct 31 • Village Halloween Parade: ThrillerNYC
Oct 1 - Nov 16
70,000 Pumpkins, Endless Fall Magic
Croton-on-Hudson
From October 1 through November 16, the Hudson Valley’s most iconic fall tradition lights up Croton-on-Hudson as The Great Jack O’Lantern Blaze takes over the grounds of historic Van Cortlandt Manor. With more than 70,000 hand-carved pumpkins glowing against the night sky, this event isn’t just a seasonal favorite — it’s a bucket-list experience that has become one of the most photogenic fall spectacles in the region.
Wander through larger-than-life pumpkin installations that defy imagination: towering pumpkin arches, swirling galaxies of jack-o’-lanterns, fire-breathing pumpkin dragons, and intricate themed scenes that change every year. Each pumpkin is carved by hand, lit from within, and arranged into displays that feel equal parts whimsical and spooky. It’s an immersive walk-through wonderland that keeps you looking up, around, and snapping photos at every turn.
Blaze is more than just a stroll — it’s an atmosphere. The crisp fall air mixes with the scent of pumpkin spice, apple cider, and seasonal treats sold on-site. Families, couples, and groups of friends flock here year after year, making it as much a tradition as apple picking or haunted houses. Timed entry keeps the flow smooth, so everyone gets a chance to linger, explore, and soak in the glowing magic without feeling rushed.
Whether you’re going for the first time or returning for your annual fall pilgrimage, Blaze is the Hudson Valley at its most dazzling. If autumn had a crown jewel, this would be it — a glowing celebration of creativity, community, and of course, pumpkins.
Details at a Glance:
📅 September 12 – November 1
🎟️ Starting at $24
📍Location:
Van Cortlandt Manor
525 S Riverside Ave
Croton-on-Hudson, NY
🎃 Over 70,000 hand-carved glowing pumpkins
✨ Larger-than-life pumpkin installations & themed displays
🍎 Seasonal food, drinks & treats on-site
🎟️ Timed entry tickets required
Oct 1- Nov 1
Ulster Park’s Darkest Tradition
Ulster Park, NY
When October rolls in, Ulster Park becomes the epicenter of fear thanks to Headless Horseman Hayrides & Haunted Attractions, one of the Hudson Valley’s most famous and spine-tingling traditions. Recognized nationally as one of the top haunted experiences in the country, this sprawling scream park isn’t just a night out — it’s a full-scale production designed to pull you into another world. From the moment the sun dips, the historic farm transforms into a nightmare landscape where every path, every corner, and every sound feels alive with menace.
The centerpiece is the haunted hayride, a chilling ride through dark woods where theatrical sets, pyrotechnics, and larger-than-life creatures keep your heart racing. But that’s only the beginning. Guests also brave multiple haunted houses, each with its own terrifying theme — think twisted carnivals, cursed crypts, and shadowy mazes. Add in the infamous corn maze and haunted walking trails, and you’re in for a relentless night of shrieks, laughs, and adrenaline.
It’s not just the scares that make Headless Horseman legendary — it’s the atmosphere. Food stands, eerie lighting, midway games, and unforgettable photo ops create an event that feels like stepping into Halloween itself. Every year brings fresh themes, new characters, and surprising set pieces, so even repeat visitors never know what’s lurking around the bend. Families with younger kids can opt for Children’s Day (October 4 and 18), which offers daylight hayrides, friendly characters, and a toned-down version of the fun.
For thrill-seekers, this is the ultimate October bucket-list event — the kind of haunt that sticks with you long after you’ve escaped. Gather your bravest crew, book your tickets early, and prepare to test your courage at the Hudson Valley’s most infamous haunt.
Details at a Glance:
📅 Weekends through October
Dusk – ~11 PM
🎟️ Starting at $69
📍 Location:
778 Broadway (Route 9W)
Ulster Park, NY
🎃 Haunted hayride, haunted houses, corn maze, walking trails, midway & food
🎟️ Tickets required
Children’s Days: Oct 4 & 18
👻 Nationally recognized haunt, new themes each year
Oct 4th - Nov 2
Dogwood Acres Family Farm Pumpkin Party
Transforms Into a Pumpkin Wonderland
Middletown, NY
Get ready, NY — Dogwood Acres Pumpkin Party is back, and it’s bigger, bolder, and more beautiful than ever. If you’re still “should I go?”-ing it, here’s your sign: this is the autumn event that’s going to make all other weekends look boring. Think crisp air, blazing pumpkins, and enough laughs and thrills to make your Instagram pop.
From October 4th through November 2nd, Dogwood Acres transforms into your ultimate pumpkin wonderland. Hours are 11 am–6 pm on Saturdays & Sundays, plus special holiday openings. Highlights include the brand-new Dogwood Express, a scenic tractor tour that gives you a sweeping view of the farm. Try your aim at the corn cannon (yes, it really shoots corn!), wander twisting corn mazes, and enjoy train rides around the pond. By sunset, the farm glows with golden light, and the smell of caramel, cider, and fresh hay fills the air.
What makes this Pumpkin Party truly special is the variety. Families can pick the perfect pumpkin, little ones can enjoy kid-friendly rides and games, and anyone looking for that picture-perfect fall moment will find endless photo ops scattered across the grounds. Between the cornfields, pumpkin patches, and colorful displays, it’s as much a visual feast as it is a day of fun.
And it’s not just about the pumpkins. Seasonal food and market finds give you something tasty to nibble on or take home. Whether it’s local treats, festive crafts, or fresh farm goodies, there’s always an extra surprise waiting beyond the pumpkin patch. Add in the playful attractions like the Dogwood Express and corn cannon, and you’ve got a day packed with fun that stretches well beyond the basics.
So mark your calendar, clean your camera roll, and wear a comfy sweater (boots optional but encouraged). Whether you’re chasing fall vistas, pumpkin spice dreams, or just need a reason to get out of the house, the Pumpkin Party at Dogwood Acres is the place to be this season. Don’t be the one hearing about it later — this is where fall memories are made.
Details at a Glance
📅 October 4 – November 2
Saturdays & Sundays, 11 AM – 6 PM + special holiday openings
🎟️ $20 GA - $35 VIP
📍Location:
Dogwood Acres Family Farm
749 Route 17M
Middletown, NY
🚂 New Dogwood Express tractor ride for sweeping farm views
🌽 Corn cannon, twisting corn mazes & pond-side train rides
🎃 Pumpkin picking, kid-friendly rides & endless photo ops
🍎 Seasonal food, local treats & festive market finds
✨ Golden-hour glow across cornfields & displays for peak fall vibes
Oct 1 - Nov 2
The World’s Largest Haunted Attraction
Monroe, NY
From October 1 through November 2 (Fridays–Sundays), the Hudson Valley cranks the fear factor to the max at Pure Terror Scream Park in Monroe. Officially recognized by Guinness World Records as the largest haunted attraction in the world, this scream park is a rite of passage for anyone who thinks they can handle October at its scariest.
At the heart of Pure Terror are 13 terrifying haunted houses, all linked together into one continuous walk-through experience. Each house has its own twisted theme, from dark forests and cursed crypts to nightmare carnivals and gothic cathedrals. You never quite know what’s waiting around the next corner — or who’s lurking in the shadows. It’s built to keep your adrenaline spiking from start to finish, no breaks, no safe zones, just pure unrelenting scares.
But it’s not just about jump scares — the park is a full-on Halloween spectacle. The midway area is alive with spooky photo ops, eerie lighting, and the perfect mix of screams and laughter as guests swap stories of their favorite frights. Food vendors, seasonal treats, and live entertainment add to the atmosphere, making it just as much a night out with friends as it is a test of bravery.
If you think you’ve seen it all when it comes to haunted houses, Pure Terror is here to prove you wrong. With its scale, detail, and relentless creativity, this park has earned its legendary status. Grab your bravest crew, because this is one Halloween event you’ll never forget — if you can make it through all 13 houses.
Details at a Glance:
📅 September 19 – November 2
Fridays–Sunday
🎟️ Starting at $50
📍Location:
1010 NY- 17M
Monroe, NY
👻 Guinness World Record: Largest haunted attraction in the world
🏚️ 13 linked haunted houses with unique themes
Oct 1–5
Equestrian Excellence Kicks Off October
Amenia, NY
From October 1–5, Amenia, NY takes center stage as the Silo Ridge Masters ushers in nearly two weeks of world-class equestrian sport. This CSI-3* showjumping competition is the kind of event that gets your heart racing — where elite riders and horses test their limits in front of a crowd buzzing with excitement. It’s the perfect kickoff, combining raw athleticism with refined elegance.
Throughout the week, spectators can watch horse-and-rider duos navigate courses that push their speed, precision, and partnership to the edge. Each day builds momentum until the $125,000 Grand Prix on Sunday, October 5, a marquee event that draws cheers, gasps, and standing ovations as riders soar over massive jumps with breathtaking accuracy. Whether you’re a seasoned equestrian fan or brand new to the sport, the intensity of the Masters makes it impossible not to get hooked.
But the Silo Ridge Masters isn’t just about competition. Between rounds, the grounds hum with energy — from curated shopping experiences to luxury hospitality offerings and gourmet bites that make the day feel elevated. It’s an atmosphere where the sport blends seamlessly with style, giving everyone from families to equestrian insiders something to savor.
In many ways, the Masters sets the tone for October in the Hudson Valley. It’s more than an event — it’s an opening chapter, laying the groundwork for the grandeur of the Highlands Cup the following week. If you want to feel the rush of equestrian sport at its finest while soaking in a weekend of fall energy and luxury, the Silo Ridge Masters is where it all begins.
Details at a Glance:
📅 October 1–5
All Day Event
🎟️ Starting at $13
📍Location:
Keane Stud / Silo Ridge
217 Depot Hill Road
Amenia, NY
🏆 CSI-3* international showjumping with elite riders & horses
💰 $125,000 Grand Prix finale on Sunday, Oct 5
🛍️ Luxury shopping, curated vendors & gourmet bites between events
🍂 Scenic fall setting in Amenia with family-friendly atmosphere
Oct 8–12
The Hudson Valley’s Premier Showjumping Event
Amenia, NY
From October 8–12, the Highlands Cup arrives to raise the stakes and crown the Hudson Valley’s biggest equestrian spectacle of the year. This isn’t just a continuation of the Silo Ridge Masters — it’s a whole new level. With both 5* and 2* competitions, the Highlands Cup attracts Olympic-level riders and internationally renowned athletes, making Amenia a must-visit destination for equestrian fans across the globe.
The competition is fierce, the stakes are high, and the atmosphere is electric. Riders like Kent Farrington, McClain Ward, Jessica Springsteen, and Lillie Keenan bring star power to the ring, creating showdowns that blend technical mastery with adrenaline-pumping speed. For five straight days, the Highlands Cup keeps spectators on the edge of their seats as riders and horses attempt to out-jump and outlast the best of the best.
But what sets the Highlands Cup apart is the culture that surrounds it. Beyond the ring, the grounds transform into a full-scale festival — think artisan vendors, fashion pop-ups, luxury lounges, and dining experiences that rival the competition for attention. It’s the kind of event where families can explore, fans can indulge, and the atmosphere itself becomes part of the thrill.
The Highlands Cup is more than a competition — it’s the centerpiece of October in the Hudson Valley. Between its championship rounds and the concerts and car show that bookend it, the Cup creates an immersive, unforgettable experience. If you’re looking for the perfect blend of sport, culture, and community, this is the event that delivers it all.
Details at a Glance:
📅 October 8–12
All Day Event
🎟️ Starting at $13
📍Location:
Highlands Horse Show Grounds
Keane Stud / Silo Ridge
217 Depot Hill Road
Amenia, NY
⭐ Olympic-caliber riders including Kent Farrington, McClain Ward, Jessica Springsteen & more
🏆 5* & 2* showjumping competitions across five thrilling days
🎶 Evening concerts featuring Third Eye Blind, Dinosaur Jr., Brothers Osborne & LeAnn Rimes
🛍️ Artisan vendors, fashion pop-ups, luxury lounges & dining experiences
🚗 Bridlemont Concours Car Show with 30+ exotic & vintage cars (Oct 12)
Oct 10- Nov 1
When Rye Playland Becomes a Nightmare
Rye, NY
Every October, Rye Playland trades its boardwalk charm for bone-chilling terror — and this year, Scared by the Sound is back to reclaim its spot as one of New York’s most infamous haunted attractions. Sprawling over 12,000 square feet of pure dread, it’s the kind of haunt that gets under your skin before you even step inside.
The moment you enter, the screams start. Twisting corridors drag you into the Crypt Walk, Haunted Wine Cellar, and Vortex Tunnel of Doom, each scene more disorienting than the last. Actors don’t just jump out — they stalk, circle, and stay right in your nightmares. Fog rolls low across your path, strobes flash in the distance, and somewhere between the mausoleum and the bayou, you’ll wonder if you’re ever getting out.
What makes Scared by the Sound legendary isn’t just the scale — it’s the atmosphere. The waterfront setting adds its own eerie soundtrack, while professional lighting, sound design, and costumes create a world that feels terrifyingly real. Every year brings new horrors — think witches, wolves, graveyards, and twisted surprises that keep even repeat visitors on edge.
This isn’t your average haunt — it’s an adrenaline rush wrapped in Halloween spectacle. With timed entry and speed passes available, the crowds stay moving but the scares never stop. If you’re ready to test your limits and earn your bragging rights, this is the haunted house that defines October on the Sound.
Details at a Glance:
📅 October 10 – November 1 (weekends + Oct 30–31)
📍Location: Rye Playland
1 Playland Parkway
Rye, NY
🎃 12,000+ sq ft haunted walkthrough with Crypt Walk, Asylum, Vortex & more
👻 Live actors, immersive sets, pro effects & new scenes every year
🎟️ Timed-entry tickets required | Speed passes available
💡 Bonus: Back at its rightful home along the Long Island Sound for maximum chills
Oct 10 -12
Where Murals, Music & Wellness Fuse Across Uptown
Uptown Kingston
From October 10–12, Kingston transforms into a living canvas for the O+ Festival, a three-day celebration where murals, indie music, and wellness collide to create one of the Hudson Valley’s most unique cultural experiences. Uptown streets, walls, and venues burst to life with art in motion as blank surfaces are transformed into vibrant murals, installations, and projection art. The city itself becomes the gallery, inviting festival-goers to wander, discover, and watch creativity unfold right before their eyes.
Music pulses at the heart of O+, with a lineup that mixes national acts, indie darlings, and local favorites. This year features icons like Kool Keith, the trailblazing hip-hop innovator, alongside The Fiery Furnaces, Rachael Yamagata, and Wild Pink. Performances pop up across Kingston’s intimate venues and outdoor stages, each show adding to the sense of discovery that makes O+ so exciting. From high-energy headliners to unexpected collaborations, the soundtrack of the weekend is as eclectic as the art that surrounds it.
What sets O+ apart is its soul. At the center of the festival is the groundbreaking Artists’ Clinic, where participating artists receive free medical, dental, and wellness care in exchange for their creativity. Beyond that, wellness programming flows throughout the weekend, offering yoga, meditation, sound baths, and movement classes designed to keep festival-goers grounded and energized. It’s a rare and powerful blend — a festival that feeds both body and spirit while supporting artists in a way that goes far beyond applause.
The theme for 2025 is PO+wer, a call to explore how creativity shapes and shares influence within a community. Every mural painted, every lyric sung, and every wellness session offered ties back to this central idea. By supporting O+, you’re not just attending another festival — you’re contributing to a mission that amplifies voices, sustains year-round care, and makes art and music a force for connection. With its mix of spectacle and soul, O+ Festival is one of the most transformative weekends you can have this October.
Details at a Glance:
📅 October 10–12
🎟️ Admission: By-donation wristbands — no one turned away for lack of funds
📍Location:
Uptown Kingston, NY
🎶 Music: Kool Keith, The Fiery Furnaces, Rachael Yamagata, Wild Pink + more indie & local acts
🎨 Art: Live mural painting, installations, projection art, street galleries
🧘 Wellness: Yoga, sound baths, meditation, movement classes, Artist Clinic offering care in exchange for art
Oct 10
Alt-Rock Legends Take the Stage
Amenia, NY
On Friday, October 10, the Highlands Cup flips the switch from equestrian adrenaline to full-blown rock spectacle. Under the arena lights, Third Eye Blind — the alt-rock icons who gave us anthems like “Semi-Charmed Life,” “Jumper,” and “How’s It Going to Be” — take the stage with the kind of nostalgic energy that has entire crowds singing every word. Pair that with Dinosaur Jr., the legendary indie-rock band known for their blistering guitar solos and wall-of-sound intensity, and you’ve got a night that blends ’90s throwback feels with raw, live-wire power.
This isn’t just another concert — it’s a collision of eras and sounds, where polished hooks meet unfiltered distortion. Third Eye Blind brings the soundtrack of a generation, while Dinosaur Jr. drops the grit that keeps the night loud and unpredictable. Together, they create a show that’s both polished and primal, polished and unpredictable — the kind of lineup you don’t stumble into often.
What makes it even more electric is the setting. You’ll spend the day surrounded by world-class showjumping and the buzz of the Highlands Cup, only to watch the arena transform into an outdoor concert venue as the stars come out. There’s something surreal about standing under the night sky in Amenia, with the echo of hooves still hanging in the air as guitars roar to life.
For anyone who grew up with these bands on repeat, or for fans who just crave live music that hits hard and stays with you, this is a can’t-miss night. Highlands isn’t just serving equestrian excellence this October — it’s serving a rock show that will have you talking long after the final chord.
Details at a Glance:
📅 Friday, October 10
Gates ~7 PM | Show ~8 PM
🎶 Third Eye Blind + Dinosaur Jr.
🎟️ Starting at $31
📍Location:
Highlands Horse Show Grounds
Keane Stud / Silo Ridge
217 Depot Hill Road
Amenia, NY
🎶 Alt-rock legends live under the stars
🌟 Hits like “Semi-Charmed Life,” “Jumper,” & more
🎸 Dinosaur Jr.’s thunderous guitars + indie edge
Oct 11 -12
Lake Placid’s Autumn Spectacle
Lake Placid, NY
Every October, Lake Placid’s Olympic Jumping Complex becomes the stage for fall’s grandest show — Flaming Leaves Festival, happening October 11–12, 2025. This is where nature’s peak foliage meets adrenaline, music, crafts, and family fun — all wrapped into one unforgettable weekend.
By day, world-class ski jumpers take to the towering HS128 and K48 jumps, competing in trials, finals, and ceremonies under blazing autumn skies. Vendors line the grounds with local flavor — from food trucks serving up hearty bites, to artisan crafts, face painting, caricatures, and live magic shows. As jumps soar overhead, the festival pulses with energy, music, and fall traditions.
But Flaming Leaves isn’t just about sport. It’s about the atmosphere — crisp Adirondack air, golden leaves, and a backdrop that makes every moment feel cinematic. Add in live music, plenty of food and drink, and the excitement of championship-level competition, and you’ve got a weekend that captures everything we love about fall in the mountains.
This one’s for everyone — families, thrill-seekers, art lovers, leaf peepers, and adventure junkies. Whether you come for the jumps, the music, the food, or just to soak in peak fall in the Adirondacks, Flaming Leaves Festival delivers. Don’t miss one of October’s most unique autumn spectacles.
Details at a Glance:
📅 October 11–12, 2025
📍 Olympic Jumping Complex
5486 Cascade Rd
Lake Placid, NY
🎿 Ski jumping competitions on HS128 & K48
🎶 Live music, craft vendors, family activities
🚚 Food trucks & local vendors
✨ Set against peak Adirondack foliage
Oct 11
Country Fire Meets Timeless Voice
Amenia, NY
On Saturday, October 11, the Highlands Cup doubles down with a lineup that blends raw country swagger and soaring vocal power. First up, Brothers Osborne, the Grammy-winning duo whose guitar riffs and rowdy anthems have turned them into one of the most exciting acts in modern country. Their live shows are nothing short of a party — loud, unfiltered, and impossible to stand still for.
Sharing the bill is the incomparable LeAnn Rimes, whose timeless voice and chart-topping hits have been part of the soundtrack of American music for decades. From powerhouse ballads to feel-good country-pop favorites, her performance promises to deliver both goosebumps and sing-along moments. It’s rare to catch a night where two acts of this caliber share the same stage, and Highlands is delivering it right in the heart of the Hudson Valley.
The atmosphere makes it unforgettable. By day, the arena is filled with the intensity of Olympic-caliber showjumping, and by night, it transforms into a concert venue under the stars. Surrounded by the energy of the Cup and the crisp October air, this show has all the makings of one of the season’s most memorable nights.
For fans of country, pop, or just live performances that deliver heart and fire in equal measure, this is your night to be there. Grab your boots, gather your crew, and don’t miss the Highlands Cup’s ultimate country-meets-classic concert experience.
Details at a Glance:
📅 Saturday, October 11
Gates ~7 PM | Show ~8 PM
🎶 Brothers Osborne + LeAnn Rimes
🎟️ Starting at $31
📍Location:
Highlands Horse Show Grounds
Keane Stud / Silo Ridge
217 Depot Hill Road
Amenia, NY
🎶 Grammy-winning country duo meets timeless voice
🔥 High-energy anthems + soulful ballads back-to-back
🌙 Daytime showjumping turns into a nighttime concert vibe
Oct 10 – Nov 2
Where Light & Wonder Dance After Dark
Bethel Woods Center For The Arts
Bethel, NY
Bethel Woods Center for the Arts is about to transform into a glowing Halloween wonderland, and this year’s Peace, Love & Pumpkins is set to be the most dazzling yet. As the sun dips, the historic grounds ignite with thousands of hand-carved jack-o’lanterns arranged into mesmerizing scenes — witches and mermaids, dinosaurs and woodland creatures, even nods to Woodstock’s legendary past. Every path glows, every corner surprises, and every moment feels like stepping into October’s most magical dreamscape.
The experience goes far beyond pumpkins. On select nights, drone shows light up the sky in synchronized bursts of color and motion. The Night Market on weekends hums with artisan vendors, live music, and food trucks that keep the good vibes flowing. Want a little extra thrill? Brave Friday Night Fright when the trail becomes haunted, or keep it playful on Boos & Booze nights where 21+ guests can sip festive cocktails as they wander. Families will love the sensory-friendly evening designed for a calmer, gentler glow, plus plenty of sweet treats and photo ops to make memories that last long after the lanterns go dark.
It’s more than an event — it’s a feeling. From the flicker of pumpkins under the stars to the laughter drifting across the fields, Peace, Love & Pumpkins captures everything we crave about fall. Whether you’re there for a cozy night out, a spooky adventure, or just to see the grounds transformed into pure autumn magic, this is the kind of October experience that will stick with you all season long.
Details at a Glance:
📅 October 10 – November 2
Wednesdays–Sundays
6:30–10 PM (last entry 9 PM)
Special Events:
Friday, October 17 – Murder Mystery Mixer: A Wedding in Transylvania (21+ only)
Wednesday, October 22 – Sensory Friendly Experience
Friday, October 24 – Friday Night Fright, a haunted walk-thru experience
Friday, October 31 – Halloween at Peace, Love & Pumpkins
Drone Shows:
October 11, 17, 25, 31 – Two 15-minute shows a night, at 7:00 PM and 8:30 PM
🎟️ Adults $25 ($30 day of)
Youth $15 ($20 day of)
Kids 2 & under free
Timed tickets required Fridays & Saturdays
📍Location:
Bethel Woods Center for the Arts
200 Hurd Rd
Bethel, NY
🎃 Thousands of hand-carved pumpkins arranged into glowing themed scenes
🚁 Drone shows on select nights — synchronized light & motion over Woodstock grounds
🍸 Boos & Booze 21+ nights with seasonal cocktails
👻 Friday Night Fright haunted walk-through & family-friendly sensory evening
🎶 Night Market with artisan vendors, live music & food trucks
Oct 11th
Fright Night at The Yard
Beacon, NY
Halloween doesn’t just creep into the Hudson Valley — it takes over. And on Friday, October 11 from 5–11 PM, Beacon becomes the epicenter of spooky season when Cirque Du Creep unleashes its infamous Fright Night at The Yard. Forget hayrides and cider sips — this is the night when phantoms, freaks, and fearless souls collide, and you’re invited to step straight into the chaos.
The Yard transforms into a dark carnival of sights and sounds. More than 50 alternative artists and vendors set up shop, hawking eerie, otherworldly creations that feel ripped from nightmares and fairy tales alike. The hum of tattoo machines buzzes in the background as ten artists offer exclusive flash sheets, ready to brand your evening in permanent ink. Onstage, live bands bring the noise while a Coney Island–style sideshow troupe pushes the boundaries of what you thought possible — sword-swallowing, fire-breathing, and spine-tingling stunts that leave you gasping. By the time the costume contest kicks off, the stakes are sky-high: cash prizes, tattoo certificates, and bragging rights fit for a king (or ghoul) of the underworld.
But Cirque Du Creep doesn’t stop at the stage. Haunt actors prowl the grounds, waiting for the perfect moment to strike. Every corner doubles as a photo op — twisted sets, creepy installations, and the kind of moments your camera roll won’t forgive you for missing. Fuel up between frights with gourmet bites, decadent sweets, and cocktails strong enough to raise the dead. This isn’t just a party — it’s a playground of fear and fun designed to keep your pulse racing all night long.
And because every monster deserves a happy ending, the festival keeps its heart in the right place. Adorable, adoptable animals from HVARS will be there, raffles support local shelters, and the sense of community pulses just as strong as the scares. It’s spooky, it’s weird, it’s wild — and it’s the kind of event you’ll be haunted by if you miss it. Cirque Du Creep isn’t just another Halloween bash — it’s the night that defines October in the Hudson Valley.
Details at a Glance:
📅 Oct 11
5pm - 11pm
🎟️ $12 presale
$15 at the door
Kids 15 & under are free.
📍Location:
4 Hana Ln
Beacon, NY
🛍️ 50+ alternative artists & vendors
💉 10 tattoo artists with exclusive flash sheets
🎶 Live music + Coney Island sideshow acts
👻 Haunt actors, creepy photo ops, & epic costume contest
🍴 Food trucks, sweets, & specialty drinks
🐾 Adoptable pets & raffles benefiting HVARS
Oct 12
Paddles, Costumes & Halloween Magic on the Hudson
Sleepy Hollow, NY
On Sunday, October 12, the Hudson River transforms into one of the spookiest — and most Instagram-worthy — sights of the season with the return of the SUP Witches of Sleepy Hollow Festival. Picture it: dozens of witches, wizards, and warlocks gliding across the water on paddleboards, costumes billowing in the autumn breeze, creating a scene straight out of a Halloween fairytale.
This is no ordinary paddle. Participants are encouraged to go all-out with costumes, hats, capes, and spooky accessories, turning the river into a floating parade of creativity. Whether you’re on a board yourself or watching from shore, the sight of so many witches casting “spells” with every paddle stroke is a moment that makes October in the Hudson Valley feel truly enchanted.
After the paddle, the festival vibe continues on land with live music, food, and community fun. It’s part fitness, part spectacle, and part party — all rolled into one unforgettable afternoon. The energy is equal parts spooky and joyful, with everyone leaning into the Halloween spirit.
With Sleepy Hollow as the backdrop, the SUP Witches Festival perfectly blends local lore with modern celebration. It’s a chance to be part of a growing Hudson Valley tradition that celebrates creativity, community, and of course, a little bit of magic. Don’t miss the chance to see the Hudson come alive with witches this October.
Details at a Glance:
📅 October 12, 2025
12pm - 4pm
📍 Sleepy Hollow, NY
Hudson River
🧙♀️ Paddleboard parade with witches, wizards & spooky costumes
🎶 Live music & community celebration after the paddle
✨ Hosted by Rivertowns SUP Yoga
Oct 12
When Horsepower Meets Horsepower
Amenia, NY
On Sunday, October 12, the Highlands Cup closes out its epic run with a finale that trades saddles for steering wheels: the Bridlemont Concours Car Show. This isn’t just a lineup of cars — it’s a rolling work of art, where more than 30 rare, exotic, and vintage vehicles gleam under the autumn sun. From chrome-laden classics to jaw-dropping supercars, every ride on display tells a story of design, speed, and pure prestige.
Walking the grounds feels like stepping into a luxury showroom that’s been dropped into the middle of the Hudson Valley. One moment you’re face-to-face with a vintage European beauty, the next you’re staring at the cutting edge of modern engineering. Motorcycles join the lineup too, adding another layer of adrenaline to an already thrilling collection. For gearheads, it’s heaven. For casual fans, it’s an afternoon of sheer spectacle.
The setting makes it even more striking. Surrounded by the Highlands Cup’s equestrian elegance and the golden hues of October, the gleam of polished cars and motorcycles feels larger-than-life. It’s horsepower in every form — a celebration of both manes and machines, with the rolling hills of Amenia as the backdrop.
As the Highlands Cup draws to a close, the Concours is the perfect exclamation point. It’s refined, it’s thrilling, and it’s a finale that captures the spirit of the entire event: world-class competition, jaw-dropping entertainment, and unforgettable fall experiences. Whether you’re a die-hard collector or just someone who loves a good show, this is the kind of ending that makes you wish October never had to stop.
Details at a Glance:
📅 Sunday, October 12
10am - 4pm
🎟️ Starting at $28
📍Location:
Highlands Horse Show Grounds
Keane Stud / Silo Ridge
217 Depot Hill Road
Amenia, NY
🚗 30+ rare, exotic & vintage cars + motorcycles
✨ From gleaming chrome classics to jaw-dropping supercars
🍂 Set against the scenic fall backdrop of Amenia
Oct 17
First Dinner Of The
Harvest on the Hudson & Half Moon Dinner Series
Your Passport to Culinary Adventure Begins
Dobbs Ferry, NY
Hastings, NY
Forget the same old dinner plans — this fall, two of the Hudson Valley’s most celebrated restaurants are inviting you on a culinary journey like no other. Harvest on Hudson and Half Moon are launching their brand-new Dinner Series + Passport Program, where every meal is more than a night out — it’s a stamp on your passport, a step closer to exclusive prizes, and an unforgettable experience along the way.
Here’s how it works: each dinner series focuses on either a theme or a region. At Half Moon, the spotlight is on Spain with the “Flavors of the World” series, complete with a tapas bar and multi-course menus that whisk you straight to the Iberian Peninsula. Over at Harvest, it’s all about imaginative themes — from a rustic Farm Dinner, to a bold Wild Game Dinner, to a full-on Lord of the Rings feast that promises as much story as it does flavor. No two nights are the same, and every dinner is designed to be immersive, delicious, and a little bit magical.
Every guest receives a passport at their first dinner. With each event you attend, your passport gets stamped — and the more stamps you collect, the more rewards you unlock. Think of it as your golden ticket to foodie bragging rights. The top prizes? VIP tickets to Harvest’s Columbus Day bash, entry to the famous Clam Bake at Half Moon, and even the chance to win a private dinner with the Chef. Whether you’re chasing one dinner or all of them, each experience brings you closer to rewards as memorable as the meals themselves.
The adventure kicks off on Thursday, October 17, with Flavors of Galicia at Half Moon — the first stop in the Flavors of the World series. Expect rustic coastal flavors, Spanish wines, and a tapas spread that’ll have you dreaming of seaside villages along the Atlantic coast of Spain. From there, the journey only gets richer, with dinners rolling out month after month, each with its own theme, menu, and passport stamp waiting for you.
This isn’t just dinner — it’s an experience, a community, and a story you get to write with every bite. So gather your crew, bring your appetite, and get ready to eat your way through the Hudson Valley’s most exciting culinary adventure.
Details at a Glance:
📅 First Dinner: October 17 – Flavors of Galicia at Half Moon
4pm - 6:30pm
🎟️ $100 per guest + $35 optional beverage pairing
📍Location:
1 High St
Dobbs Ferry, NY
🇪🇸 Series Themes: Spanish regional dinners at Half Moon
🧝🏻♂️ Themed dinners at Harvest on the Hudson (Farm, Wild Game, Lord of the Rings & more)
📖 Passport: Collect stamps at each dinner, unlock bigger prizes
🎁 Top Prizes: VIP tickets to Harvest’s Columbus Day event, Clam Bake at Half Moon, Private Chef’s Dinner
👗 Atmosphere: Elevated, fun, and immersive — dress for the story you’re stepping into
Oct 18 & 19
When Darkness Beckons, Answer
Carmel,NY
On October 18 & 19, Putnam County Veterans Memorial Park sheds its daytime calm and morphs into something far darker — the stage for Spellbound Festival, a two-night immersion where theater, haunt, and Halloween collide. Haunted trails snake into the woods, firelit performances erupt against the night sky, and the 19th-century village of Ashbury pulls you into a story you can’t step out of. This isn’t a festival you simply attend — it’s one that swallows you whole.
Ashbury isn’t just a set, it’s alive. Lantern-lit streets are crowded with costumed villagers whispering tales of a vanished girl, strange magicians bending reality in front of your eyes, and clowns and mimes materializing out of nowhere before vanishing back into shadow. Every corner holds a question: are you a spectator, or are you already part of the tale? The longer you stay, the harder it is to tell.
Performances crash in waves, keeping your pulse racing. Fire dancers carve sparks into the dark, aerialists twist and turn high above the crowd, and gothic rock outfit Black Rose Burning fills the night with a moody soundtrack that ties it all together. The Mystic Market tempts you with eerie artisan goods, while food trucks and sweet treats lure you back to reality just long enough to catch your breath before plunging back into the unknown.
Families, don’t fear: daylight brings its own brand of magic, with trick-or-treating trails, playful ghostly adventures, and just enough spectacle to enchant even the littlest ghouls. But when the sun sets, the veil lifts, the park shifts, and Spellbound becomes something else entirely — a climactic celebration of spooky season where October itself feels alive.
Details at a Glance:
📅 Oct 18 - 19
Sat - 3pm - 9pm
Sun - 2pm - 8pm
🎟️ Start at $15 online
($5 teens, kids under 11 free) Weekend Passes Available
📍Location:
10 Gleneida Ave
Carmel, NY
🎭 Immersive haunted village of Ashbury with live performers & storylines
🔥 Fire dancers, aerialists, gothic rock, and firelit spectacles
🛍️ Mystic Market, food trucks, family trick-or-treating by day
👗 Costumes encouraged | Re-entry allowed
Oct 18
Steins, Bands & Bavarian Spirit
Lake George, NY
On Saturday, October 18, Lake George goes full Bavarian as Adirondack Brewery Oktoberfest returns for one day only. This 21+ event is the Adirondacks’ ultimate fall party — overflowing with beer steins, live music, and the kind of high-energy atmosphere that makes Oktoberfest a bucket-list tradition. Even better? It’s all for a good cause, with proceeds supporting local charities in the Lake George community.
Expect Adirondack Brewery’s best seasonal pours alongside guest taps, giving beer lovers a wide range of styles to sample. Whether you’re craving crisp lagers, malty märzens, or pumpkin-spiced brews, there’s a glass waiting with your name on it. Add in hearty Bavarian eats, pretzels bigger than your head, and the clink of steins echoing through the festival tents, and you’ve got the perfect recipe for an autumn afternoon done right.
The music lineup keeps the energy high all day long, blending traditional polka vibes with local bands that’ll have the crowd dancing between sips. Lawn games, contests, and Oktoberfest staples like stein-holding challenges add to the fun, making it more than just a beer fest — it’s a full-on experience.
If you’ve been looking for an excuse to round up your crew, pull on some lederhosen (or at least a cozy fall flannel), and celebrate the season Bavarian-style, this is it. With Lake George’s autumn views as the backdrop, Adirondack Brewery Oktoberfest delivers a one-day fall escape you won’t want to miss.
Details at a Glance:
📅 October 18, 2025
📍 Adirondack Brewery
33 Canada St
Lake George, NY
🍺 21+ charity beer festival with Adirondack Brewery & guest taps
🥨 Bavarian food, stein-holding contests, games & giveaways
🎶 Live music all day
Brews, Bites & Fall Vibes at Clover Stadium
Pomona, NY
On Saturday, October 18, Clover Stadium in Pomona transforms into a foodie playground where hops meet handhelds at the Hudson Valley Craft Beer & Food Truck Festival. For one glorious afternoon, the field becomes your tasting table, overflowing with local brews and a fleet of food trucks ready to serve everything from juicy BBQ and crispy tacos to gourmet grilled cheese and decadent desserts.
Beer lovers will find themselves spoiled for choice, with Hudson Valley breweries pouring seasonal favorites, crisp lagers, bold IPAs, and yes — those pumpkin-spiced brews that practically scream October. Every sample is a chance to discover something new, whether you’re chasing that perfect hazy IPA or sticking with smooth, malty comfort pours. Pair it with plates from the trucks parked all around the stadium, and you’ve got the perfect balance of flavor and fun.
But this festival isn’t just about eating and drinking (though that’s reason enough). Clover Stadium’s open-air setting makes for an unbeatable autumn hangout, complete with live music to soundtrack your sips and bites. Friends gather at communal tables, beer in hand, while the air fills with laughter, conversation, and the unmistakable aroma of food truck magic drifting across the grounds.
It’s the kind of Saturday that defines October — casual, delicious, and packed with energy. Whether you’re a craft beer connoisseur, a food truck junkie, or just looking for the perfect fall day out with friends, this festival has all the ingredients for a memorable weekend.
Details at a Glance:
📅 Saturday, October 18
12–5 PM
🎟️ Tickets start at $55 (includes unlimited beer samples; food sold separately)
📍 Location:
Clover Stadium
1 Palisades Credit Union Park Dr
Pomona, NY
🍺 Local breweries pouring seasonal & specialty craft beers
🚚 Food trucks serving everything from BBQ to sweet treats🎶 Live music & open-air fall vibes all afternoon
Oct 19
Sip, Savor & Support a Great Cause
Staatsburg, NY
On Saturday, October 19, wine lovers and community supporters alike will gather for an evening that’s equal parts indulgence and impact: the Greystone Programs’ Wine Tasting & Auction. Set in a casual yet elegant “vineyard chic” atmosphere, this annual event raises vital funds for Greystone’s expressive arts therapy and enrichment programs, directly supporting individuals living with autism and other intellectual or developmental disabilities. With every sip and every bid, guests play a role in helping creativity, confidence, and connection flourish.
The evening blends sophistication with heart. Attendees will enjoy curated tastings from Hudson Valley wineries, paired with gourmet small plates from local chefs that highlight the region’s rich culinary talent. Every pour and every bite feels like a celebration of community and craft, designed to be savored in the company of friends, neighbors, and fellow supporters.
Adding to the experience is an inspiring art showcase created by individuals supported by Greystone Programs. This gallery is more than just beautiful artwork — it’s a testament to the power of expression, creativity, and opportunity. Guests can explore these works before diving into the night’s most anticipated moments: the silent and live auctions, featuring unique gifts, curated experiences, and one-of-a-kind treasures waiting to be claimed.
With plenty of on-site parking, a welcoming atmosphere, and a cause that touches lives, this isn’t just another night out — it’s a chance to make a difference while enjoying the best of the Hudson Valley. Come ready to sip, savor, and show your support. Together, we can turn an evening of wine and wonder into lasting possibilities for so many.
Details at a Glance:
📅 Saturday, October 19
1pm - 5pm
📍Location:
450 Hollow Rd
Staatsburg, NY
🍷 Curated Hudson Valley wine tastings
🍴Gourmet small plates from local chefs
🎨 Art showcase by individuals supported by Greystone Programs
🔨 Silent & live auctions with unique experiences and gifts
👗 Casual dressy, vineyard chic
🚗 Plenty of on-site parking
Oct 26
Cider, Apples & Autumn Magic Every Weekend
Hopewell Junction, NY
Every weekend through October, Fishkill Farms transforms into a full-on fall celebration, pairing crisp Hudson Valley apples with the farm’s own hard cider at the Fall Harvest Festival. This is one of those quintessential October outings — the kind where the air smells like cinnamon, the orchards are bursting with color, and every corner of the farm buzzes with autumn energy.
Pick-your-own is the heart of the day. Guests can wander the orchards for apples and pumpkins, stopping along the way to soak in sweeping views of rolling farmland and fiery foliage. Kids race through hayrides and farm activities, while adults can sneak off to the Treasury Cider Bar for a tasting flight of small-batch ciders made right on the property. It’s fresh, it’s local, and it’s the kind of sip that tastes exactly like October in the Hudson Valley.
Beyond the orchards, the festival grounds come alive with live music, family-friendly entertainment, and plenty of eats to keep you fueled. Think wood-fired pizzas, hearty farm fare, apple cider donuts, and seasonal treats that demand at least one “food photo” for your feed. Artisan vendors set up shop with handmade goods and local specialties, making the festival feel as much like a makers’ market as a farm day.
Whether you’re here for the orchard strolls, the cider pours, or just to spend a crisp fall day surrounded by the best the season has to offer, the Harvest Festival is the kind of tradition you’ll want to mark on your calendar year after year. It’s family-friendly, flavor-packed, and unapologetically autumn.
Details at a Glance:
📅 Weekends through October 26
📍 Location:
Fishkill Farms & Treasury Cider
9 Fishkill Farm Rd
Hopewell Junction, NY
🍎 Pick-your-own apples & pumpkins with orchard views
🍻 Treasury Cider Bar with flights & pours of farm-made cider
🎶 Live music, family activities & hayrides
🍴 Wood-fired pizza, cider donuts, farm-fresh eats & local vendors
🎟️ Admission varies; pre-purchased tickets recommended
Oct 31
Thriller Takes the Streets
Manhattan, NY
Every October 31, Manhattan’s Village Halloween Parade turns into a spectacle of costumes, puppets, dance, and delight — but the night reaches its peak when ThrillerNYC leads the streets in synchronized zombie choreography. Dancers from all over join in, turning Sixth Avenue into a spooky stage where Michael Jackson’s “Thriller” becomes a parade-wide performance.
The Parade starts around 7:00 PM, weaving its way up Sixth Avenue from Canal Street to 15th (or 16th) Street. By the time the Thriller group hits the route, the crowd is already electric — city lights, costumed participants, giant puppets, community groups, and thousands of onlookers all merged into one moving party.
If you love Halloween, street theater, dance, or just want to be part of something iconic — this is your night. Even if you’re not participating, standing at the sidelines as zombies shuffle and sing in unison is one of those moments you’ll remember.
Details at a Glance:
📅 October 31
7:00 PM
📍Location:
Sixth Avenue
Manhattan, NY
(Canal → 15th/16th Street)
💀 ThrillerNYC leads the parade with synchronized zombie performance
🎭 Costumes, puppets, performance groups, dancers & cross-community pageantry
🎟️ Free to watch (street viewing)
So there it is — October in all its chaotic, pumpkin-spiced glory. From witches paddling the Hudson to rock shows that shake the horse arena, your weekends are basically screaming at you to get outside. Forget FOMO, this month is straight-up “fear of sitting still.”
Your to-do list? Simple: eat, drink, dance, scream, repeat. Swap ghost stories at the fire pit, juggle steins like a pro (or at least pretend), and don’t let the pumpkin-carving pros make you feel bad about your lopsided masterpiece. By the time November shows up with its turkey and chill vibes, you’ll have already won fall.
Now grab your crew, pack your weekends tight, and go make October jealous it can’t hang out with you.
Never Stop Exploring!
HVH Team
