6 Not-So-Spooky Halloween Events in Fairfield County (2023)

I often joke that Halloween is the never-ending holiday. By the time October 31st rolls around, most parents have already gotten their little ghosts and goblins in and out of their costumes no less than 13 times.

Although it can make you feel a bit batty at times, it truly is one of the most spooktacular times of the year! And best of all, the bootiful festivities don’t need to be too frightful to be fun.

The last thing mummy needs is her little pumpkins throwing a tantrum at the neighborhood Halloween party because they’re too scared! Here are 6 Not-So-Spooky Halloween Events You Won’t Want to Miss in Fairfield County.

Nocturnal Animals: A Halloween Costume Benefit at Greenwich Audubon Center, Greenwich, CT

On Friday, October 20, 2023 at 7:00 pm, gather at the Greenwich Audubon Center, 613 Riversville Rd, Greenwich, CT for an exciting evening of Halloween fun! 

This will undoubtedly be an amazing evening filled with fascinating activities and unexpected surprises.

Please note: This is an adults only, 21+ event

Attendees are encouraged to dress up in their most creative costume for the celebrity-judged costume contest for a chance to win spooktacular prizes! 

Enjoy creepy entertainment from a mind-blowing Mentalist, get up close and personal with some intriguing nocturnal critters, and dance the night away to spooky tracks played by a wicked DJ. 

Our food trucks will be serving wickedly tasty snacks, and artistically made beverages will be available for drinking throughout the evening.

Tickets: $350 for one and $1,000 for two

Online registration is open! Purchase a ticket or donate here.

Halloween events Fairfield County
Photo Credit: Greenwich Audubon Facebook Page

Halloween on the Green, Fairfield, CT

This free day of fantastic fun is not to be missed! 

Fairfield’s most spirited annual family event, Halloween on the Green, will take place on October 29th from 12:00 pm – 4:00pm.

The entire area behind the Fairfield Museum & History Center will be transformed into an enchanting Halloween village with elaborate Halloween displays. 

The entire family is invited to come in costume (that includes you!) for an afternoon full of spooktacular celebration. 

Attractions include trick-or-treating, bounce houses, games, hayrides, crafts, music, performances, giveaways, and food trucks. 

Halloween events Fairfield County

Westport Halloween Window Painting Contest- Westport, CT

When: October 28, 2023 from 9:00 am to 4:00 pm

Details: Westport merchants offer their windows for painting.  

Kids will get the opportunity to paint a window requested or assigned to them. 

Judges will come around in the next few days and determine winners based on three different criteria and age/school (Elementary, Middle School, High School). 

1. Scariest Art Work 2. Best Halloween Theme and 3. Most Original. 

There will be 6 total winners.  Sign up online.

Beasties and Besties Halloween Bash

All small ghosts and goblins, unite! Prepare for an exciting evening of Halloween fun at Stepping Stones Museum for Children’s spooktacular after-hours event, Beasties & Besties.

Gather around professional storytellers with warm drinks and apple cider doughnuts in hand for tales ranging from not-so-spooky to seriously spine-tingling!

You can choose your own adventure as you tour our modified BOO-seum, with different levels of terrifying flare highlighted at each story stop.

Remember to come dressed in your most imaginative costumes, and prepare for a night of mesmerizing shows and dramatic adventures.

 BOO-tiful moments are in store!

Tickets: 

General Registration Available Starting October 9 – October 21

Member: $18, Non-Member: $25

Halloween events Fairfield County
Photo Credit: Stepping Stones Museum for Children Facebook Page

Pumpkin Decorating, Darien, CT

When: October 26, 2023 or October 27, 2023 from 3:30 pm to 4:30 pm

Where: Darien Nature Center at 120 Brookside Road, Darien, CT

Come for outdoor creative fun for the whole family!

You will use natural materials gathered from Cherry Lawn Park to create festive decor pumpkins for Halloween.

Sessions are outdoors, behind Darien Nature Center.

Please bring a drop cloth, and all other materials provided. 

In the case of rain, pick up your pumpkin(s) and decorating kit to enjoy at home. 

Adult supervision is required, this is not a drop-off event.

$20 per family.

Halloween events Fairfield County
Photo Credit: Darien Nature Center Facebook Page

New Canaan Annual Halloween Block Party, New Canaan, CT

When: October 29, 2023 from noon-2:00 pm. Park Street parking lot

Details: New Canaan’s Annual Halloween Block Party is back this year!

Kids and dogs of all ages are invited to New Canaan’s downtown to show off their costumes.

The first 500 attendees will receive a free pre-stuffed bag courtesy.

There are also prizes by Pet Pantry for costumed dogs.

Halloween events Fairfield County
Photo Credit: Silvermineart.org

About Lauren Haley

Lauren Haley was born and raised in Darien, CT. Lauren is the founder of Busy Little Bee. As a busy mom looking for activities for her girls, Lauren always found herself spending hours on various websites comparing schedules, costs, and class descriptions. And when it came time to start the daunting task of finding a preschool, it was impossible for her to locate a quick overview of each school’s approach to learning or identify open house and registration dates. Lauren quickly realized that navigating the logistics of activity registration and preschool enrollment didn’t need to be so difficult, so Busy Little Bee was born! Lauren lives in Darien, CT with her husband, Chris, and three children, Parker, Madison, and Hudson. Website: www.busylittlebee.com

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