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🎃 Westchester's Biggest Halloween Party Returns This Weekend

Trick-or-treating at Lyndhurst, a costume party with Westchester SC, plus a gated 2-acre Bedford home under $1.25m

Hello, Westchester!

 
The Halloween ramp-up is getting serious now and the event calendar around the county definitely reflects it. You can’t drive anywhere without seeing haunted lawns or posters for spooky events. But we’re not really trying to avoid it either, are we?
 
What we are trying to avoid, for now at least, is the “Christmas creep,” which is getting earlier and earlier. We’ve already caught a couple of Christmas ads in the midst of our kids’ endless YouTube consumption. Those holiday tunes plus some recent unseasonably warm weather must be what it feels like in Australia in December.
 
Perhaps Westchester’s biggest seasonal bash, the Sleepy Hollow Block Party, is upon us this weekend. Here are two things we know for sure: 1. The Halloween vibe is unbeatable in Sleepy Hollow, and Beekman Avenue for the Block Party is where it shows through the most, 2. Everyone else thinks so too, so local traffic might be the spookiest thing happening on Saturday night. This was originally meant to be a two-day party but Friday was already cancelled due to a rainy forecast, meaning all the festivities will go down on Saturday. Try to have a plan in place to get there and take our word for it. Last year, we found out about Sleepy Hollow backroads we never knew existed and once the police diversions start, it’s impossible to get out of them.
 
Finally, Westchester SC plays their final home game of the 2026 season Saturday night in Mount Vernon. They’ve unfortunately fallen just short of the playoffs this year but have taken huge strides from last year’s inaugural season when they finished last in the standings, jumping up to 10th this year, as of today.
 
Entry for Saturday’s match is free for fans who come in costume, and to make it sweeter, Hutch the Ram’s Halloween Kickoff starts at 5:30p, with fans trick-or-treating through the stadium concourse. Let’s send off the boys in style with a packed (costumed) crowd.
 
Enjoy the weekend, and if you’re headed to Saturday’s match, see you there!
 

 
Loving Westchester is written by a real-life husband and wife team, completely free, and in your inbox every Tuesday and Friday. If it adds something to your week, contributions help us keep growing - including our first in-person Loving Westchester event we're working toward for the fall.
 
"Thank you for your emails highlighting the wonderful events happening throughout Westchester. They are such a great resource and reminder of how much Westchester has to offer." — A Loving Westchester Reader

 
In today’s edition:

And a message from our partners, QueenBHive, giving you, your business, or brand the visibility and support it needs, and QueenBPoker, hosting your epic game night.

 

Now let’s get to it!

💓 The Pulse

Loving Westchester’s Featured Events!

🎃 Trick-or-Treat Weekend at Lyndhurst
Sat.-Sun., Oct. 17-18 | Lyndhurst Mansion, Tarrytown | Sat. 9a-3p, Sun. 9a-4p | $5-$30
Trick-or-treat along the winding pathways of Lyndhurst’s historic 67-acre estate, in costume with your treat bag, stopping for candy at marked spots on the map. Add mansion entry to roam the Halloween-decorated rooms at your own pace. Food from Geordane’s and Jimmy’s Soft Serve on site, a Saturday puppet show, and Sunday face painting.
Grab the map, fill the bag, then wander a mansion dressed for the season →
 
🎃 Sleepy Hollow Haunted Hayride and Block Party
Sat., Oct. 17 | Sleepy Hollow | Block party 5p, Hayride 7p | Ticket prices vary
Climb aboard a wagon down the Albany Post Road, past Philipsburg Manor and the Old Dutch Church, tracing Ichabod Crane’s flight from the Headless Horseman through the dark woods of the hollow. The ride itself isn’t terribly scary, but the wait can be, so there’s a free block party on Beekman Avenue with live music, entertainment, family activities, and vendors.
Follow Ichabod’s exact route through the real Sleepy Hollow, if you keep your head →
 
🎃 Hocus Pocus Family Screening with Shannon Carlin
Sun., Oct. 18 | Shames JCC on the Hudson, Tarrytown | 3p-5p | $8+, children 5 and under free
Gather the family for the Halloween classic, then stick around for a conversation with oral historian Shannon Carlin, author of Witches Run Amok: The Oral History of Disney’s Hocus Pocus. She shares behind-the-scenes stories and fun facts, moderated by Hocus Pocus superfan and collector Allison Dubrosky. Signed books for sale.
See the movie, then hear every secret from the set →

 

Got 99 ideas, but can’t execute 1?

 
Hey, everybody. This is Bec.
 
I’ve spent 20 years helping businesses, brands and community organizations grow through better strategy, communications and partnerships. If you’re a local business owner with 100 ideas but never enough time to move them forward, that’s exactly why I created QueenBHive. Think of me as the person in your corner. Helping you decide what matters most, connecting the right dots, creating momentum, and making sure the good ideas actually happen. Whether that’s your visibility, social content, a launch, a partnership or simply having someone strategic to think alongside.
 
Send me a message and let me be your WingWoman.

 

📆 What’s Happening?

Family Fun!

🎃 Family Fun at nest & nook: Halloween Music and Play
Sat., Oct. 17 | nest & nook, Thornwood | 10a and 11:30a | Ticket prices vary
Two Halloween classes with Rock’n’Rascalz: Music, Movement and Play for ages 0-3 at 10a, then a Freeze Dance Party for ages 4-9 at 11:30a, with pizza and treat bags.
 
🎃 Briarcliff Nursery School Fall Fest and Open House
Sat., Oct. 17 | 40 Morningside Drive, Ossining | 10a-1p | Free
A free morning with a petting zoo, pumpkin decorating, face painting, carnival games, live music, and a pizza truck.
 
🛍️ The Goblin Market
Sat., Oct. 17 | Hudson Valley Writers Center, Sleepy Hollow | 10a-3p | Free
The Hudson Valley Writers Center hosts an October pop-up of artwork, crafts, and goods from Sleepy Hollow creators. Pair it with other free same-day markets nearby: the TaSH Farmers Market in Tarrytown (8:30a-1:30p), the Christ Church / San Marcos Fall Fair in Tarrytown (10a-4p), and the Warner Library Fall Book Sale in Tarrytown (10a-5p).
 
🍂 Spooktoberfest
Sat., Oct. 17 | Hart’s Brook Park and Preserve, Hartsdale | 12p-4:30p | $7, children under 2 free
Greenburgh’s autumn festival at Hart’s Brook Preserve with hayrides, inflatable mazes, children’s entertainment, and live music in the woods.
 
🎬 Disney’s Legend of Sleepy Hollow and Hotel Transylvania
Sat., Oct. 17 | The Lyceum, Tarrytown | 5p | $13+
A family double feature from Sleepy Hollow Cinema’s Home for Horror series: Disney’s 1949 animated Legend of Sleepy Hollow (narrated by Bing Crosby) followed by Hotel Transylvania (2012). Rated PG.
 
⚽ Westchester Soccer Club vs. Union Omaha
Sat., Oct. 17 | The Stadium at Memorial Field, Mount Vernon | 7p | $10+
Westchester SC’s final home game of the 2026 season, hosting Union Omaha on Yonkers and Irish Heritage Night with a pre-match Halloween costume kickoff.
 
🍺 Spooktacular Oktoberfest at Edith G. Read Wildlife Sanctuary
Sat.-Sun., Oct. 17-18 | Edith G. Read Wildlife Sanctuary, Rye | 1p-5:30p | $25 (under 3 free)
Two days of trick-or-treating, hay rides, a haunted house, pumpkin painting, s’mores, a bounce house, and live music. Come in costume.
 
🛍️ Wickers Creek Market
Sun., Oct. 18 | Dobbs Ferry Waterfront Park | 10a-4p | Free
A vintage market with 50-plus vendors selling mid-century furniture, collectible dĂŠcor, and estate finds, plus food and live music.
 
🎨 Pumpkins and Hot Cocoa: A Kids Sip and Paint
Sun., Oct. 18 | Movie House Mews, Hastings-on-Hudson | 12p-1p | Ticket prices vary
A kids’ pumpkin-painting party with hot cocoa at Movie House Mews Promenade. Each child takes home a decorated pumpkin.
 
🏮 Autumn Glow Festival
Select evenings | Glen Island Park, New Rochelle | 6:30p-10p | $18.99+
A nighttime walk through hundreds of hand-crafted LED Chinese lanterns, with local food, drink, and photo ops throughout.
 
⚡ Harry Potter: A Forbidden Forest Experience
Fri.-Sun., Oct. 16-18 | FDR State Park, Yorktown Heights | Evening timed entry | Ticket prices vary (Children under 3 enter free)
Opening its 2026 season Friday night: a 60-90 minute illuminated woodland trail with creatures and scenes from Harry Potter and Fantastic Beasts, interactive wand spell-casting, and a Patronus-summoning experience.
 
🌙 Mystic Moon at Harvest Moon
Fri.-Sun., Oct. 16-18 | Harvest Moon Farm & Orchard, North Salem | Evening timed entry | $39+ (Ages 3 and under are free)
A 40-minute trail through 80-year-old orchard trees and illuminated woods, with glowing forest scenes, costumed characters, and zero jump scares.
 
🎃 The Great Jack O'Lantern Blaze
Fri.-Sun., Oct. 16-18 | Van Cortlandt Manor, Croton-on-Hudson | Evening timeslots | $24+ (Advance purchase only; ages 2 and under are free)
More than 7,000 hand-carved, illuminated pumpkins across an 18th-century estate, with glowing structures, synchronized lighting, and custom music.
 
🏘️ Twilight Village in Sleepy Hollow
Fri.-Sun., Oct. 16-18 | Philipsburg Manor, Sleepy Hollow | Evening times vary by night | $25+
The village grounds transformed by fog and colored lights, with live storytelling, fire performers, a roving brass band, s’mores pits, and the arrival of the Headless Horseman.

 

 

Grown Ups & Date Nights

🎸 The Rascals 60th Anniversary Tour
Fri., Oct. 16 | Paramount Hudson Valley Theater, Peekskill | 8p | $68.50
Rock and Roll Hall of Famer Felix Cavaliere’s Rascals mark six decades of “blue-eyed soul,” playing hits “Groovin’,” “Good Lovin’,” and “People Got To Be Free.”
 
🎭 Peek-a-Boo: An Immersive Hudson Valley Haunt
Select dates through Oct. 25 | Bethany Arts Community, Ossining | Ticket prices vary
River’s Edge Theatre’s immersive show, inspired by the real Peek-a-Boo flats of Tarrytown, follows Hudson Valley characters like Hulda the Witch through dark secrets and scandalous confessions. Mature audiences only.
 
🎉 Up the River’s One Year Anniversary and Blocktoberfest
Sat., Oct. 17 | 34 Main Street, Ossining | 12p-8p | Free
Up the River marks its first year by shutting down the block, with local artisans and vendors, live music, and oysters from Here Coffee + Beer. Spend $100 to enter a drawing for an all-inclusive Caribbean vacation.
 
🚢 Wobble on the Hudson Sunset Cruise: Fall Foliage Edition
Sat., Oct. 17 | Fleischmann Pier Park, Peekskill | Boarding 3:30p, Cruise 4p-7p | $55
A three-hour line dance cruise with Steve “Fun Bunch” Dillard spinning soul, R&B, and southern soul, with fall foliage and sunset views on the Hudson.
 
🎸 Rock n Roll Fest: Feeding Westchester Benefit
Sat., Oct. 17 | The Grand, Croton-on-Hudson | 7p | $30
A benefit for Feeding Westchester with live music from Jack Toad and No Guardrails, plus beer donated by Captain Lawrence Brewery. Every dollar raised provides two meals for kids, seniors, and families at risk, with a goal of 20,000 meals.
 
🎶 Songwright: Westchester’s Songwriting Circle
Sat., Oct. 17 | Mercy University Recording Studio, Dobbs Ferry | 7p | Free (suggested donation $20)
Westchester’s songwriting circle gathers for a night of original work, featuring Nev Cadesca, Lucas Rotman, Mike Death, and Siobhan O’Malley.
 
🎸 Daniel Donato's Cosmic Country
Sat., Oct. 17 | The Capitol Theatre, Port Chester | 8p | $35+
A fusion of jam-band energy, psychedelic rock, americana, and honky-tonk country, with Donato on guitar.
 
😂 Westchester Comedy Club at Pelham: Saturday Night Laughs
Sat., Oct. 17 | Pelham Rails, Village of Pelham | 8p-9:30p | Ticket prices vary
A stand-up night with four NYC comedians: Christina Walkinshaw, KP Anderson, Nikhil Mehta, and Ben Rosenfeld.
 
🎃 Puff and Carve: A Friendly Pumpkin Carving Night
Sat., Oct. 17 | The Overlook at Valley Greens, Peekskill | 8p-9:30p | Ticket prices vary
A 21+ pumpkin-carving night in the lounge at The Overlook, with music and light snacks.
 
🎭 The Rocky Horror Picture Show Interactive Screening and Sing-Along
Sun., Oct. 18 | The Green Growler, Croton-on-Hudson | 7p | Free entry, $15 presale package
An interactive screening and sing-along honoring the late Tim Curry. Come in costume. The $15 presale package reserves a seat and includes a drink voucher and a prop bag.
 
👻 Scared by the Sound
Select evening slots available | Rye Playland, Rye | $29+
Westchester’s seaside haunted house returns for its 25th season with over 12,000 square feet of Hollywood-style sets, live actors, and waterfront horror. Not recommended for under 12.

 

🃏 Game nights are having a moment in Westchester…

 
…and if you've ever wanted to host a poker or casino night without the stress of figuring out the rules or rounding up chips, QueenBPoker is the answer. They come to your home, venue, or office, and handle everything you may need from teaching the table to running the night. Casual, corporate, charity. No experience needed, just people who want a good time.
 
Plan your game night →

🎃 Headless Horseman Hayrides and Haunted Attractions
Fri.-Sun., Oct. 16-18 | Headless Horseman Haunted Attractions, Ulster Park | 7p-9p | $73.90+
Thirteen haunted attractions sprawling across 65 acres, including a themed hayride, walking trails, haunted houses, a magic show, and a two-acre corn maze.

🎃 Hudson Valley Fall Festival at Kelder’s Farm
Through Nov. 1 | Kelder’s Farm, Kerhonkson | 10a-6p (closed Wed.) | Ticket prices vary
Pumpkin picking, a corn maze, weekend hayrides, and 35-plus farmyard attractions with farm animals, plus food, drink, and a taproom with local beer, wine, and cider. The season closes with a Pumpkin Smash on Oct. 31 and Nov. 1.
 
😂 Anthony Rodia: Insanely Funny Tour
Fri., Oct. 16 | Palace Theatre, Stamford, CT | 8p | $36+
The Westchester-born comedian behind the viral “Road Rage Wednesday” and his Uncle Vinny and Zia Lucia characters, with over 22 million YouTube views, brings his stand-up to Stamford.
 
😂 Tim Dillon
Select shows Oct. 16-17 | West Nyack Levity Live, West Nyack | $49.22+
The stand-up comedian, actor, and host of The Tim Dillon Show, seen in Eli Roth’s Thanksgiving and Joker: Folie à Deux, plays a multi-night run with Fri. shows at 7p and 9:15p and Sat. shows at 6:30p and 9p.

 

🏡 Where the Heart Is

Incredible homes are listed in Westchester every week. Here’s one that caught our eye

 

The Key Details: 4 bedrooms, 3 bathrooms, approximately 2,568 square feet on about 2 acres ($467 / square foot)
 
What We Love About It: Two gated acres in Bedford with a semi-private pond and an in-ground Gunite pool, listed at $1.2 million. The existing four-bedroom, three-bath home sets up a renovation for someone with a vision, and the schools are both rated 9/10. Mature trees add privacy, and Bedford Village, with its historic Playhouse, boutiques, and restaurants, is moments away. Bring your own plans and make it a country estate that’s yours.
 

We love to hear from you! Give us a shout at [email protected] or find us on Instagram @lovingwestchester. And don't forget to forward this to a friend who's always asking "what's going on this week?"
 
See you out there!