the busy mom's guide to preschools and activities for her busy little bee

Halloween Happenings 2019

2019 Halloween Happenings

To view events by date click here.

Please note: some events require pre-registration. Be sure to check individual event links for additional info!

And don't forget to check our Fall Fun List for more seasonal events & festivals!


Pumpkin Decorating

Where: Darien Nature Center
When: Tuesday-Thursday, October 23-25 from 3:30pm-4:30pm
Cost: $15 per pumpkin
Details: Children ages 2+ will use natural materials to decorate pumpkins for Halloween. Let us keep your creation to display at our annual Hoot n’ Howl party (October 27) and you will receive free admission to that event! Children 5 and older can be dropped off!

Halloween Parade with Amazing Andy

Where: Downtown Darien
When: Friday, October 25 at 10am
Cost: $5 per child
Details: Our parade is a colorful tradition! Dress up your little ones and bring a bag for trick-or-treating at the doors of local merchants along the way to Tilley Pond. Then join us for snacks and a special show with our favorite magician “The Amazing Andy.” His magical talents will amaze you and your child, and his wonderful antics, humor and sleight of hand will keep even the youngest magic enthusiasts entertained.

Halloween Family Fest

Where: Darien Arts Center
When: Saturday, October 26 from 9am-12pm
Cost: FREE!
Details: Bring the whole family and join us for a spooky good time! Activities for ages 3 & older: Pumpkin Painting, Mask Making, Coffee, Donuts, Candy, Sing-Alongs, 'Spooky' Stories, and Drop-In Dance Classes! Wear your costume!

Dance Party & Costume Contest

Where: Dance on the DL Studio
When: Saturday, October 26 from 6pm-8:30pm
Cost: $25 per child
Details: Kick off Halloween weekend at DL Studio. Learn the Thriller Dance, play games and enter to win the DL Costume Contest with first, second and third place prizes awarded to the most creative costumes. Open to kids ages 6-12. Pre-registration is required.

Post 53 Annual Haunted House

Where: Darien EMS - Post 53 Headquarters
When: Sunday, October 27 from 1pm-4pm
Cost: FREE! (all donations will support Post 53)
Details: Get your Halloween costumes ready! The afternoon will be filled with exciting events and fun games for kids of all ages. The Haunted House offers three different levels of fright. There will also be ambulance tours, pumpkin decorating, face painting, and many more games and treats!

Spooky Family Films: "It's the Great Pumpkin, Charlie Brown"

Where: Darien Library
When: Sunday, October 27 from 2pm-3pm
Cost: FREE!
Details: Join us for a spooky film for the whole family! In the 1966 animated special It's The Great Pumpkin, Charlie Brown, the Peanuts gang celebrates Halloween, with Linus hoping that, finally, he will be visited by The Great Pumpkin, while Charlie Brown is invited to a Halloween party.

Halloween Hoot and Howl

Where: Darien Nature Center
When: Sunday, October 27 from 4pm-6pm
Cost: $5 per person (children under 1 are free)
Details: This family event features not-too-spooky fun including crafts, a magic show, s’mores and storytelling around a campfire, face painting, a fall hike, refreshments and animal encounters.

Halloween Storytime

Where: Darien Library
When: Wednesday, October 30 from 9:30am-10am
Cost: FREE!
Details: Join the children’s library for a special Halloween-themed Toddler Tales. Come in costume and trick-or-treat in the library afterwards!

Halloween Crafts

Where: Darien Library
When: Thursday, October 31 from 4pm-4:30pm
Cost: FREE!
Details: Come and celebrate the holiday in the Children's Library by joining us for a special "crafternoon" that will put you in a spooky mood!



Halloween on the Green

Where: Fairfield Museum & History Center
When: Sunday, October 27 from 12pm-4pm
Cost: FREE!
Details: Families are invited to come in costume for a day of free, fantastic fun! This family event will feature trick-or-treating, giveaways, performances, music, food trucks, bounce houses, games, hayrides, crafts, activities and more! The beloved Costume Parade begins at 1:00pm! Elaborate Halloween displays will be set up in the historic buildings on the Museum Commons and the entire area will be transformed into an enchanting Halloween village.

Halloween Ragamuffin Parade

Where: Fairfield Library - Main Library
When: Thursday, October 31 from 10am-11am
Cost: FREE!
Details: Join us for our Halloween celebration! Come in costume as we gather in the Children’s Department to parade around the Library and do some trick or treating! Enjoy fun games and special seasonal activities.

Photo Credit: Darien Nature Center Facebook Page
Photo Credit: Darien Nature Center Facebook Page

Where: Sam Bridge Nursery
When: every Saturday in October anytime between 10am & 2pm
Cost: $39 per scarecrow
Details: We provide the head, face pieces, hair, and hay for stuffing. You provide a long sleeve shirt, long pants and any other accessories that you’d like to add. Get creative! A winner will be chosen!

Pumpkin Painting

Where: Sam Bridge Nursery
When: every Saturday in October anytime between 10am & 2pm
Cost: $10 per pumpkin
Details: All ages are invited to come get creative and paint a pumpkin!

Make a Ceramic Ghost with Lucia

Where: Byram Shubert Library
When: Saturday, October 19 from 10:30am-11:30am
Cost: FREE!
Details: Just in time: join Lucia in this hands-on Halloween themed craft and bring home a scary, creative object to decorate your room and home. This program is for the entire family.

Where: Greenwich Botanical Center
When: Saturday, October 19 from 4pm-7pm
Cost: Members: $15 per child, $25 per adult; Non-Members: $20/child, $30 per adult
DetailsJoin Greenwich Botanical Center for Ghouls in the Garden, our annual Halloween-themed celebration in Greenwich’s own spooky forest, the Montgomery Pinetum. The afternoon is filled with fun family activities including a costume parade, spook walk, pumpkin decorating contest, prizes and tasty refreshments.

Halloween Celebration and Puppet Show

Where: Cos Cob Library
When: Friday, October 25 from 3:30pm-4:30pm
Cost: FREE!
Details: The Staff and Friends of Cos Cob Library present a puppet show titled Magnificent Monster Circus. Children are invited to come in costume and goody bags will be distributed at the end of the show. This is a drop-in program and seating is limited.

Halloween Happening *Greenwich residents only

Where: Bendheim Western Greenwich Civic Center
When: Friday, October 25 from 6pm-8pm
Cost: $10 per child & $8 per adult
Details: Come in costume and bring a medium-sized pumpkin to decorate! Play games from 6pm-7pm in Dracula’s Den and dance from 7pm-8pm. Entertainment will be provided!

Halloween Weekend

Where: Greenwich Audubon Center
When: Friday, October 25 from 6:15pm-9pm & Saturday, October 26 from 2pm-9pm
Cost: $13 per person ($15 at the door)
Details: Join Greenwich Audubon Center for a howling good time! Come enjoy our Frightful Forest and scare-free Enchanted Meadow and Costume Parade, Creepy Crawly Critter Show, bonfire, s’mores, and bake sale.

Pumpkin Harvest Walk

Where: Greenwich Land Trust
When: Tuesday, October 29 from 5pm-6:30pm
Cost: FREE!
Details: Come celebrate fall at GLT’s Mueller preserve with a stroll through our meadows, woodland, and gardens, stopping at our pumpkin patch where participants can pick a pumpkin to take home. We’ll also harvest gourds, read a Halloween story, and enjoy cider and popcorn. Space is limited, pre-registration is required.

Music with Margie: Halloween Music Time
Where: Greenwich Library
When: Thursday, October 31 from 11am-12pm
Cost: FREE!
Details: It's Halloween! Join Margie Warner in the Greenwich Library Children's Room for a fun Halloween themed preschool music time.

Halloween Blast Scary Stories!

Where: Byram Shubert Library
When: Thursday, October 31 from 5pm-6pm
Cost: FREE!
Details: Carol Birch began telling stories in 1971 and will tell some very scary stories. After the reading, join us for a Trunk-n-Treat with lots of candy!

Photo Credit: Audubon Greenwich Facebook Page
Photo Credit: Audubon Greenwich Facebook Page

New Canaan

Pumpkin Painting Party *New Canaan residents only

Where: Waveny House
When: Tuesday, October 15 from 4pm–5pm
Cost: $13 per child
Details: Children ages 4-10 are invited to enjoy a special pumpkin painting party. We will have small pumpkins and acrylic paint for each child to create their very own design. We will also have some refreshments to enjoy, Halloween decorations, and Halloween coloring.

Halloween Witches Ball *New Canaan residents only

Where: Waveny House
When: Friday, October 18 from 6pm–8pm
Cost: $18 per person
Details: Waveny House is transformed into a Halloween House with fantastic decorations and special lighting! Come in costume, dance to the music, and enjoy activities including the mummy wrap, monster mash, witches broom limbo and more. Door prizes will be distributed throughout the event and we will also have some refreshments to enjoy. Appropriate for children ages 3-12 and a parent.

Halloween Art Party

Where: Silvermine Arts Center
When: Sunday, October 20 from 2pm–4pm
Cost: $20 per child
Details: Join us for a howling good time! Costume Parade, Spooky Art Creations in every room, Clay Pumpkins, Goody Bags, Sweet Treats, Spooky Movie.

Halloween Spooktacular

Where: New Canaan Nature Center
When: Friday, October 25 from 6:30pm–8:30pm
Cost: $10 for Members, $15 for Non-Member
Details: Get into the Halloween spirit by joining us for this spooktacular celebration, NCNC-style. We’ll learn about and meet some creepy critters who remind us of All Hallows Eve (spiders, bats, snakes, & more), before getting the chance to make our very own slime. We’ll wrap up the evening by enjoying a spooky & interactive Halloween story and a one-of-a-kind jack-o-lantern experience. Registration Deadline: 12pm on Thursday, October 24.

Halloween Parade & Block Party

Where: Downtown New Canaan
When: Sunday, October 27 from 12pm-2pm
Cost: FREE!
Details: Ghosts, goblins, fairy princesses, superheroes, children of all ages and their dogs are invited to head in to town and show off their costume. Grandparents and residents are invited to join us and take lots of pictures of the various, sometimes wholly original, characters. Head into town in your costume and enjoy music and entertainment.

The Spooky Music, Bubble, & Comedy Halloween Parade

Where: New Canaan Library
When: Monday, October 28 from 4:30pm-5:15pm
Cost: FREE!
Details: The Spooky Music, Bubble & Comedy Halloween Parade engages children with comedy, singing, spiders, bats, bubbles, ghouls & a monster mash dance party for kids! This 45 minute show has hands-on visual & sensory experiences to help kids learn & have fun!

Photo Credit:
Photo Credit:


Halloween Hay Bale Theater

Where: Stew Leonard’s
When: Friday, October 11 & Friday, October 18 from 6:30pm-7:30pm
Cost: FREE!
Details: Stew's Hoedown will be transformed into a Hay Bale Theater to show a free children's Halloween-themed movie! Complimentary juice and popcorn are served to all.

Mini Pumpkin Decorating

Where: Norwalk Library
When: Sunday, October 20 from 2pm-4pm
Cost: FREE!
Details: Come decorate a mini pumpkin. While supplies last! Ages 3-10.

Trick-or-Treat with the Stew Leonard’s Characters

Where: Stew Leonard’s
When: Wednesday, October 23 from 4pm-5pm
Cost: FREE!
Details: Children are invited to dress in their costumes and come to Stew Leonard’s to go trick or treating! Children are kindly asked to bring their own reusable trick or treating bag. Stew Leonard’s famous characters, including mascot Wow the Cow, will be available for taking photos with the children at the stations.

Halloween Party

Where: Tumble Jungle
When: Friday, October 25 from 4:30pm-6pm
Cost: Members: $20, Non-Members: $25
Details: Join us for a spooky fundraising evening of trick or treating for Unicef! Costume party with prizes, a scavenger hunt, spooky arts & crafts, obstacles & inflatables, and more! Ages 3+.

Monster Mash

Where: Stepping Stones Museum for Children
When: Friday, October 25 from 5pm-8pm
Cost: Members: $10 per person (after 10/18, $12 per person; Non-Members: $15
per person (after 10/18, $17 per person)

Details: The main event is the wickedly-cool performance by the kookiest and spookiest of all mad scientists, Dr. Diabolical. The tricks and treats don’t end on the stage, however! There is an endless list of science-themed spooky activities for the whole family to
enjoy. Plus, if all that isn’t enough, Monster Mash kicks off Stepping Stones’ “ Tricks and Treats Week ” from 10/25-10/31. A week of spooky fun leading up to Halloween!

Halloween Spooktacular

Where: Westport/Weston YMCA Gymnastics Center (in Norwalk)
When: Friday, October 25 from 5:30pm-7pm
Cost: $5 per child (pay at the door)

Details: Calling all ghosts and goblins! Join the fun, wear a costume, parents stay! Family friendly activities for children up to age 10.


Where: Stew Leonard’s
When: Friday, October 25 from 6pm-8pm
Cost: $1 per child
Details: Children, along with their families, will trick or treat from the trunks of dozens of decorated cars in the store’s parking lot. A panel of Stew Leonard’s Team Members will also vote on the Trunk or Treat car that features the best spooky or wacky decorations! 1st place will win a $250 gift card to Stew Leonard’s while 2nd place will win $150 and 3rd place will win $50.

Barkfest Dog Halloween

Where: Stew Leonard's
When: Saturday, October 26 from 10:30am-11:30am
Cost: FREE!
Details: This Halloween, dogs are invited to Stew Leonard’s for a howling good time at the store’s first Barkfest! Customers may bring their pups dressed in their best Halloween costumes and enter for their chance to win a Bubba’s Barkery Gift Basket valued at $100, which contains fresh dog treats made in-house at Stew Leonard’s. To enter a dog, shoppers are kindly asked to bring a small bag or can of dog food and all collected dog food will be donated to a local pet shelter.

Halloween Spooktacular

Where: Norwalk Library - SoNo Branch
When: Tuesday, October 29 from 4pm-6pm
Cost: FREE!
Details: Children of all ages are invited to have a delightfully spooky time as Bob Conrad performs using music, magic and a fun surprise! Children are welcomed to come dressed in their costume and participate in our annual library parade. I spy with my little eye and trick or treat before the show!

Decorate a Trick-or-Treat Bag

Where: Norwalk Library
When: Wednesday, October 30 from 9am-5pm
Cost: FREE!
Details: Drop in and have your child decorate a bag for Halloween!

Halloween Parade with Ms. Karen

Where: Norwalk Library
When: Wednesday, October 30 from 10am-11am
Cost: FREE!
Details: Show off those costumes and participate in storytime with Ms. Karen before parading around the library to pick up treats. Come early to decorate a bag for trick or treating!

Free Ice Cream Day

Where: Stew Leonard's
When: Thursday, October 31 from 10am-9pm
Cost: FREE!
Details: A yearly tradition! Children ages 12 and younger who come to the store in their costumes will receive a free small ice cream!

Photo Credit: Friends of Sherwood Island State Park  Facebook Page
Photo Credit: Friends of Sherwood Island State Park Facebook Page


RCA Halloween Celebration

Where: Rowayton Community Center
When: Sunday, October 20 from 1pm-4pm
Cost: FREE!
Details: Come in costume to explore the hay maze, decorate a pumpkin, pet the animals, grab a goody bag, take a pony ride and parade with your peers! Don’t forget about the costume contest run by the Rowayton Parents Exchange!

Pumpkin Palooza

Where: Green Moon Art Studio
When: Friday, October 25 from 4pm-5pm (drop off!) & Saturday, October 26 from 9am-12pm
Cost: Friday: $50, Saturday: $40 in advance or $60 at door
Details: Come dressed to impress in your best costume and decorate pumpkins!



Preschool Movie Matinee

Where: Ferguson Library - Main Library
When: Thursday, October 17 & 24 from 10:15am-10:45am and October 31 from 12pm-12:30pm
Cost: FREE!
Details: Thirty minutes of picture book movies based on our most beloved fall and Halloween-themed children’s books!

My Gym Halloween Party

Where: My Gym Stamford
When: Friday, October 25
Cost: $20 per child for Members, $30 per child for Non-Members
Details: Join us for our Halloween Party! We will be running Halloween games, activities and more. Come in costume and see all your favorite My Gym teachers! Party times are as follows: 3:30-4:30: 2 year olds & under, 4:45-5:45: 3 year olds & older, 6:00-7:00: all ages.

Preschool Halloween Party

Where: Stamford Recreation Star Center
When: Friday, October 25 from 10am-11:15am
Cost: $12 per child
Details: Mom, dad, grandparents and caregivers, come join us with your little one dressed in costume for this fun Halloween event. Children will be involved in games like pin the tail on the pumpkin, bean toss, Bobbing for gummy worms, Pumpkin Bowling, music, Pumpkin Ring Toss, Costume parade, Halloween treats and more! You must pre-register for this event as space is limited to 30 children.

Monster Dash

Where: Stamford Family YMCA
When: Saturday, October 26 beginning at 8am
Cost: $25 per adult, $12 per child, free for under 4
Details: The race has something for everyone. A flat fast course through Downtown Stamford, starting in Columbus Park, two loops around Scalzi Park, and finishing at the Y. It’s a fun, costumed event with judging for best costumes! There’s a 1mile fun run for children and families. A great Halloween post-race party, with festive music and Halloween games and great food.

Mill River Park Spooktacular

Where: Mill River Park Collaborative
When: Saturday, October 26 from 10am-4pm
Cost: Free admission, individual activities $1 each
Details: Enjoy festive activities like: Pick-Your-Own Pumpkin Patch in the Meadows, Free Games and Play Section, Bounce Amusement Zone, Creepy Crafts, "Glam-o-Ween" Area featuring Glitter Tattoos, Fire Pits & S'mores.

Halloween Storycraft

Where: Ferguson Library - Main Library
When: Saturday, October 26 from 11am-12pm
Cost: FREE!
Details: Show off your costume and join us for some of our favorite Halloween (not-so) spooky stories. We’ll finish by making a craft you can take home. For ages 3 1⁄2 to 8.

Pumpkins on the Porch

Where: Ferguson Library - Weed Memorial & Hollander Branch
When: Saturday, October 26 from 2pm-4pm
Cost: FREE!
Details: Pumpkin crafts and activities for families.

Trick or Treat on Heckscher Farm

Where: Stamford Museum & Nature Center
When: Sunday, October 27 from 1pm-3pm
Cost: $5 per family for Members, $5 per family plus gate admission for Non-Members
Details: Come in costume and trick or treat with your favorite farm friends! Follow the clues to find stations throughout the farm. There will be toys or candy at each station, as well as nut free options. Don’t forget your trick-or-treat bag! Then, visit Heckscher WILD! for a chance to meet some cool creepy crawlies and stop by the Overbrook Nature Center’s “Ick Fest” to get slimy with our slime table, visit live reptiles and bugs, and create crafts around some of our favorite Halloween critters!

photo from
photo from


Shivers at Sherwood

Where: Sherwood Island State Park
When: Saturday & Sunday, October 19 & 20 from 4pm-6pm
Cost: $5 per car
Details: The Friends of Sherwood Island have been relishing the fun of transforming the Nature Center into a Haunted House and collecting bats, spiders, ghosts, tombstones and more! Join us for ghoulish fun and seasonal favorites. Face painting, bob for apples, carve pumpkins. Enjoy live music Warm yourself by the bonfire. Or…brave the Haunted Nature Center where creatures of the night have taken over!

Halloween Family Music Jam

Where: Music Together Studio
When: Friday, October 25 from 5:30pm-7pm
Cost: $25 per family
Details: Singing, Dancing, Instrument Play, Costume Parade, Craft, Photo Booth. Come for a spooky good time!

Halloween Parade

Where: Downtown Westport
When: Tuesday, October 29 at 3:30pm
Cost: FREE!
Details: Children may trick or treat along Main Street and in Town Hall and then meet on the Green for refreshments, a small gift, and live entertainment!


Pumpkin Parade

Where: Wilton Center
When: Saturday, October 26 from 2:30pm-4:30pm
Cost: FREE!
Details: Trick or Treat in Wilton Center! Stop by all our shops, restaurants and retailers. Get your treats and shop local!

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