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

Halloween Happenings 2018


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!


Holly Pond School Family Fun Day

Where: Darien YMCA
When: Sunday, October 21 from 11am-2pm
Cost: $30 per family
Details: This fun-filled family event is open to the public and is designed for preschool and elementary school aged children. Exciting events include: live entertainment, pony rides, bounce houses, games, arts & crafts, pumpkin decorating, bake sale treats, and much more!

Pumpkin Decorating

Where: Darien Nature Center
When: Tuesday-Thursday, October 23-25 from 3:30pm-4:30pm
Cost: $10 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 28) and you will receive free admission to that event! Children 5 and older can be dropped off!

Halloween Crafts

Where: Darien Library
When: Thursday, October 25 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! Ages 3 and up.

“Mom's Morning In” Halloween Parade

Where: Darien Community Association
When: Friday, October 26 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. Meet at the parking lot next to the Darien Fire Station opposite Post Corner Pizza.


Where: Noroton Presbyterian Church
When: Sunday, October 28 from 3pm-5pm
Cost: FREE!
Details: Decorate your car (if you'd like)! Bounce house, free gift basket raffle, activities, candy, & more!

Halloween Hoot and Howl

Where: Darien Nature Center
When: Sunday, October 28 from 4pm-6pm
Cost: $5 per person (adult or child). Children under 1 are free.
Details: Our 16th annual Halloween Hoot and Howl event is filled with Fall fun for the entire family! Enjoy a hay ride, night walk on the trails, magic show, children’s campfire stories, festive crafts, face painting, games, and more! Costumes voluntary.

Halloween Storytime

Where: Darien Library
When: Wednesday, October 31 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! Walkers up to 3 years old.

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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 after each workshop and a grand prize winner will be chosen at the end of the month.

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!

Halloween Celebration and Puppet Show

Where: Cos Cob Library
When: Friday, October 26 from 3:30pm-4:30pm
Cost: FREE!
Details: The Staff and Friends of Cos Cob Library present a Halloween celebration and puppet show of the Pied Piper of Hamelin performed by Cactus Head Puppets! 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.

Lantern Stroll

Where: Greenwich Land Trust
When: Friday, October 26 from 4:30pm-6pm
Cost: $20 per family for Members, $25 per family for Non-Members
Details: Join us for a family-friendly stroll in the woods on a lantern-lit trail through the Mueller Preserve. We’ll also have autumn arts & crafts, stories in the barn, cider and popcorn.

Halloween Happening *Greenwich residents only

Where: Bendheim Western Greenwich Civic Center
When: Friday, October 26 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!

Where: Greenwich Botanical Center
When: Saturday, October 27 from 10am-5pm
Cost: $75 per family for Members, $100 per family for Non-Members (up to 5 family members)
Details: Join us for a ghoulishly delightful day of family fun! Come in your Halloween costume! Enjoy games, crafts, refreshments, and an amazing pumpkin decorating contest! A pumpkin and other goodies are provided with your ticket. Additional pumpkins and treats will be available for purchase. 

Halloween Craft

Where: Greenwich Library
When: Saturday, October 27 from 12pm-2pm
Cost: FREE!
Details: Children ages 5 & older are invited to visit the Children's Room craft table for a fun Halloween craft!

Scare-Free Costume Walk CANCELED

Where: Audubon Greenwich
When: Saturday, October 27 from 4:30pm-6pm
Cost: $13 per person
Details: The Enchanted Meadow welcomes children to show off their own costumes as they take a magical tour to meet friendly animal characters. Other scare-free activities will include a bake sale and bonfire with s’mores. Attendees will also get to meet live animals up close with two Creepy Crawly Critter Shows!

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New Canaan

Pumpkin Painting Party *New Canaan residents only

Where: Waveny House
When: Monday, 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 19 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 Spooktacular

Where: New Canaan Nature Center
When: Friday, October 26 from 6:30pm–8pm
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. Costumes are encouraged.

Halloween Parade

Where: Downtown New Canaan
When: Sunday, October 28 at 12pm
Cost: FREE!
Details: A New Canaan tradition! At 12pm booths open with fun activities, balloon animals, goody bags, live music & performances! At 1pm the parade begins! The parade kicks off from the parking lot preceding the corner of Park & Elm. It then travels down Elm St to Main St, and loops back up Elm St.

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Halloween Hay Bale Theater

Where: Stew Leonard’s
When: Friday, October 12 from 6pm-7:30pm & Friday, October 19 from 6:30pm-8pm
Cost: FREE!
Details: Stew's Hoedown will be transformed into a Hay Bale Theater to show a free children's Halloween-themed movie! The doors open 15 minutes in advance and seating is on a first come first-serve basis.

Trick-or-Treat at Stew Leonard’s

Where: Stew Leonard’s
When: Tuesday, 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. The Garden Shop will have candy stations for kids to stop at. Children can come with their own bags, or Stew Leonard’s will provide one for them. Stew Leonard’s famous characters, including Wow the Cow and many others, will be available for taking photos with the children.

Halloween Party

Where: Tumble Jungle
When: Friday, October 26 from 4:30pm-6pm
Cost: Members: $20, Non-Members: $25
Costume party with prizes, a scavenger hunt, spooky arts & crafts, obstacles & inflatables, and more! Ages 3+.

Halloween Spooktacular

Where: Westport/Weston YMCA Gymnastics Center (in Norwalk)
When: Friday, October 26 from 5:30pm-7pm
Cost: $5/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.

Trunk-or-Treat at Stew Leonard’s

Where: Stew Leonard’s
When: Friday, October 26 from 6pm-8pm
Cost: $5
Details: Sign-up and decorate your car in a spooky, silly or wacky theme. Each participating “trunk” should be prepared with enough candy or party favors for about 100 kids. If your car wins, Stew Leonard's will make a $250 donation to a charity of your choice!


Where: Maritime Aquarium
When: Saturday & Sunday, October 27 & 28 between 10am & 5pm
Cost: FREE! admission for children in costume when accompanied by a paying adult
Details: There's no trick about this treat as the Aquarium transforms into the Aqua-Scarium with special activities and lots of family fun!

Monster Mash

Where: Stepping Stones Museum for Children
When: Saturday, October 27 from 4pm-8pm
Cost: Members: $10/person, Non-Members: $15/person, Under 1: free (all prices go up after October 13)

Details: Prepare for a boo-tiful, too-cute-to-spook "Halloween Tricks and Treats" event! Stepping Stones Boo Squad is casting a wickedly-fun museum makeover that will inspire and delight!

Halloween Parade with Ms. Karen

Where: Norwalk Library
When: Tuesday, October 30 from 2pm-3:30pm
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!

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Paper Plate Spider Web Craft

Where: Rowayton Library
When: Tuesday, October 16 from 3:45pm-4:30pm
Cost: FREE!
Details: Kids ages 4 & under and their caregivers are invited to come to the library to make their very own paper plate spider web. Dress for mess!

Get Spooky with Pop-Up Monster Cards

Where: Rowayton Library
When: Thursday, October 18 from 3:45pm-4:30pm
Cost: FREE!
Details: Join us in making spooky pop-up monster cards to get in the spirit of Halloween. Glue will be involved, so dress for mess! Ages 5 & up.

Pumpkin Palooza

Where: Green Moon Art Studio
When: Friday, October 19 from 4pm-5pm (drop off!) & Sunday, October 21 from 3pm-5pm
Cost: Friday: $50, Sunday: $40 before or $60 at door
Details: Come dressed to impress in your best costume and decorate pumpkins!

RCA Halloween Celebration

Where: Rowayton Community Center
When: Sunday, October 21 from 1pm-4pm
Cost: FREE!
Details: Come in costume to explore the hay maze, pet the animals, take a pony ride, and parade with your peers!

Monster Dash

Where: Rowayton Community Center
When: Sunday, October 28 at 9am
Cost: $30 per adult, $15 per kid 7-15, free for kids 6 & under (prices go up after October 21)
Details: Families come out in costume for a 1K Family Fun Run/Walk. Lots of prizes to be awarded for best costumes!

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Where: Stamford Family YMCA
When: Saturday, October 27 beginning at 8am
Cost: $25 per adult, $12 per child 5+, 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 1 mile fun run for children and families. A great Halloween post-race party, with festive music and Halloween games and great food.

Halloween Storycraft

Where: Ferguson Library - Main Library
When: Saturday, October 27 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 haunted house craft you can take home. For ages 3 1⁄2 to 8.

Trick or Treat on Heckscher Farm

Where: Stamford Museum & Nature Center
When: Sunday, October 28 from 1pm-2:30pm
Cost: $5 per family for Members, $5 per family plus gate admission for Non-Members
Details: Come in costume and let the clues lead you around the farm to find some goodies for your trick or treat bag! Each clue will take you to a new animal location. The first clue will be available at the otter bridge starting at 1pm and ending promptly at 2:30pm. Stations will close at 3pm. Visit Heckscher WILD! for a chance to meet some cool creepy crawlies and stop by the Overbrook Nature Center building for self-guided crafts and our popular slime table!

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MakerLab Pumpkin Patch

Where: Westport Library
When: Saturday, October 13 from 10am-12pm
Cost: FREE!
Details: We’re exploring different materials and ways to craft pumpkins. Drop-in to the MakerLab for pumpkin making stations using yarn, beads, paper and more. For ages 5 & older (those under 8 will need adult assistance).

Children's Halloween Art Party

Where: Silvermine Arts Center
When: Sunday, October 21 from 2pm-4pm
Cost: $20 per child
Details: Please join us for a howling good time! Events include a scary movie, goody bags, & sweet treats. There will be spooky art creations in every room, including clay pumpkins and glow-in-the-dark fun. Costumes optional.

Family Haunted Trail MOVED INDOORS

Where: Westport Weston Family YMCA
When: Saturday, October 27 from 4pm-6pm
Cost: $7 per child ahead of time, $10 per child day of
Details: Participants will walk through the main path of Mahackeno participating in fun Halloween related activities. We will have pumpkin painting for the first 30 people who register. Our Haunted Trail ends with s’mores and music in one of our pavilions.

Halloween Craft

Where: Terrain
When: Sunday, October 28 from 10am-11am
Cost: $20 per child
Details: Bring along the little ones to create a mini pumpkin craft, just in time for Halloween!

Halloween Parade

Where: Downtown Westport
When: Monday, 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!

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