October 30, 2025

11th Annual Halloween Gala Recap

For over a decade, Willowdale Estate has transformed the Arts and Crafts-style mansion into a place of mystery and magic for one unforgettable night each October. This year, our theme for our 11th Annual Halloween Gala was Cult Classics, “a Twisted Tribute to Iconic Films and Fan Favorites"!   

Located just north of Boston, Willowdale Estate is known for its rich history, lavish grounds, and timeless architecture. During the gala, every corner of the mansion comes alive with creative costumes, vibrant energy, and an atmosphere that has eerie elegance.  Even our dedicated staff dresses in costumes for the event! 

  

Guests took “Cult Classic” costume inspiration from favorite B-movies, TV shows, niche graphic novels, or beloved book characters. Our visitors wandered through immersive spaces inspired by legendary cult classics. Beetlejuice, Back to the Future, The Breakfast Club, and Wizard of Oz were some themed rooms throughout the estate. A live DJ kept the dance floor packed all night, and photo stations gave guests the chance to strike a pose and flaunt their costumes. 

  

We offered signature drinks and delicious snacks – some favorites were the mac and cheese with bacon and brussels sprouts, barbecue ribs, and mini tacos. Also offered were our tried-and-true Willowdale chocolate chip cookies, homemade dirt cups, and a self-serve candy bar overflowing with sweet treats. 

 

Willowdale Estate is known for going above and beyond, so this event is more than your average costume party; it’s an immersive experience.  Handmade costumes are always encouraged, and our annual Costume Contest brought out incredible creativity and friendly competition. Our 2025 winners are as follows: 

 

3rd Place – Spaceballs, a terrific group costume tribute to a beloved cult-classic!  

2nd Place – Red Riding Hood is a complete custom and chilling rendition of the folk tale. Truely a head to toe-chilling look.   

1st Place – Mary Poppins – complete with a 3D printed parrot parasol, custom corset, and a personality as sweet as a "a spoonful of sugar’!  

Winners were sent home with baskets of spooky goodies & generous gift cards to Briar Barn Inn! 

 

Willowdale Estate thanks all of our amazing guests who showed up and truly showed out for our Halloween Gala. Every year, we’re taken aback by the amount of effort and care put into the creation of costumes. We’re already brewing up ideas for next year’s Halloween Gala, and trust us, you won’t want to miss what’s coming next October! 

 

Share your favorite moments with us by tagging @WillowdaleEstate on Instagram and Facebook. We love seeing your creativity come to life. 

 

Event Design: Willowdale Estate Events Team @willowdaleestate 

Band (Tent): Hot Mess Boston | @hotmessboston 

DJ in our Mansion: C-Zone Entertainment | @czonemusic 

Event Photography: Dan Aguirre Photography @danaguirrephoto 

Event Portraits: Ebersole Photography @ebersolephoto 

Catering and Custom Cocktails: Willowdale Estate @willowdaleestate 

Lighting Design: SociaLight @socialightboston 

Balloon Installations: Fig Balloon Co. @figballoonco 

Furniture: Party Excitement @partyexcitement 

Linen: PEAK @peakeventservices 

Dancefloor: Willowdale Estate @willowdaleestate 

Custom Dance Floor Wrap: That's INKredible @thatsinkredible 

Dessert Cart: The Frosty Pedal @thefrostypedal 

Giveaway Partner and Special Guest: @goatgirlofsalem 

Costume Contest Sponsors: Briar Barn Inn @briarbarninn, Sorel @sorelofficial, Elvira Gin from Aa Above, So Below Distillery @aasb.distillery, and Sailor Guevara @sailorguevara 

Red smoke billowing near a stone building at night, illuminated by colorful lights.
Group in costumes, one in gold armor, standing under string lights at night.
A man in a black and white striped outfit stands by a decorated table with candles.
Group in costume surrounded by green balloons.
Rustic wooden shelf with framed quotes and glassware.
Six people pose in colorful outfits amid green balloon arches at an event.
Red draped backdrop with banner and red floral wreath display.
People in Halloween costumes laughing at a party.
People in costumes dancing outdoors at night, surrounded by colorful leaves.
Wood-paneled hallway with mirrors, a white door, and a red tricycle.
Candy jars on a striped tablecloth, warmly lit in a wooden room.
Four people in colorful costumes, posing outdoors at night.
Candles lined up on a decorated dinner table with black and white linens.
Party-goers in costumes, dancing under blue streamers.
Skeleton in an upright coffin with colorful lights and plants in the background.
Courtyard with string lights at nighttime. Brick walls illuminated with red lights.
Red and black devil costume with axe, holding basket, festive setting.
Green balloon arch and columns in a decorated event tent.
Assorted beverage cans and bottles on a counter with scattered drink coasters.
Costumed people at a party with colorful lighting and drinks in hand.
Dancing in costume at a lively party, wearing a black hat and dress.
Dining room with Halloween decorations and inflatable striped creature.
Shelves with books and decor, Shermer High School banner, chalkboard sign.
Candy buffet with red and white striped tablecloths in a dimly lit room.
Five people in colorful costumes pose together outdoors at night.
Dessert table with pastries, wooden drawers, and globe decoration at an outdoor event.
Blonde woman in yellow jumpsuit holding a samurai sword, standing outdoors at night.
Floating candles suspended in a dimly lit room.
Two people in costume, smiling and hugging outdoors at night.
Four people in elaborate Halloween costumes with red and black details, standing outdoors.
A stone house at night with people gathered near warm lights.
Two people in Halloween costumes pose under night lights.
Elegant tented event space with green balloon decorations.
Person in a costume car with a Union Jack design in a fun, colorful setting.
Dimly lit bar interior with neon sign and string lights.
Woman in a colorful dress with stars and a bus design, smiling.
Tray of appetizers with forks at an event on checkered floor.
Three people in casual outfits, posing outdoors, smiling warmly.
Wooden shelves with black crow decorations and cobwebs in a rustic room.
Two people in creative costumes under dim lights outdoors, one with a metallic umbrella.
Party with guests in costumes, decorated with lights and a Back to the Future poster.
Crowd at a nighttime outdoor party with string lights and autumn decorations.
A group of people in colorful costumes, posing outdoors at night.
Man in black costume with bat-like wings and red sunglasses, standing outdoors at night.
Party guests in Halloween costumes gather under string lights indoors.
Courtyard at night, string lights overhead, and a brick building illuminated in red.
Candy buffet with jars of colorful sweets and a hand reaching for a treat.
Outdoor night party with string lights, people socializing and seated around round tables.
Two people in colorful, retro outfits standing together outdoors at night.
Three people in festive attire, one holding a mannequin, smiling under green party lights.
Two people in Halloween costumes, one in white, the other in red and black.
Mascot character in formal attire, standing against a stone wall with warm lighting.
Shelves with books and decor, Shermer High School banner, chalkboard sign.
Couple posing in a balloon arch decorated with green and gold balloons.
Costumed group at a lively party, wearing dinosaur and explorer outfits.
Group in various colorful costumes, standing in a festively lit room.
Party with guests in costumes, decorated with lights and a Back to the Future poster.
Candles lined up on a decorated dinner table with black and white linens.
Courtyard at night, string lights overhead, and a brick building illuminated in red.
Elegant tented event space with green balloon decorations.
Five women in costumes posing and smiling at a party.
Costume party with people celebrating, wearing colorful outfits and accessories.
A stone house at night with people gathered near warm lights.
A man and woman in Halloween costumes laughing together indoors.
Two people in costume at a party, one holding a plush toy, under string lights.
Five people in Halloween costumes, smiling in a warmly lit outdoor setting.
Two people in goat masks at a costume party, one in black and one in pink, under warm lighting.
Colorful party with people in costumes dancing and playing musical instruments.
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