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Best Fairfield-Area Halloween Events: Trunk or Treat, Parades, and More

The Darien Halloween Parade is a little
The Darien Halloween Parade is a little "magical" for kids. Photo courtesy of Darien
10/2/19 - By Ally Noel

Halloween seems to get bigger and better every year—and I'm not just talking about the size of the candy bars. Back in the day, we were happy just to trick or treat in our neighborhood, but now, you can find a fun Halloween event pretty much any day, all October long. Here around Fairfield, we have a huge variety of activities devoted to the spookiest holiday, from trunk or treat events to costume parades to pumpkin festivals. Our Connecticut Halloween Guide has you covered, but don't forget to subscribe to our weekly newsletters and keep tabs on our event calendar so that you won't miss any newly added Halloween fun.

 

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Families really deck out their rides (interplanetary or otherwise) at Redding's Trunk or Treat. Photo courtesy of Redding Neighbors and Newcomers
Families really deck out their rides (interplanetary or otherwise) at Redding's Trunk or Treat. Photo courtesy of Redding Neighbors and Newcomers

Fairfield Trunk or Treat Events

Trunk or Treat Street

Redding
Register in advance to host a trunk! Trunk set up is from 1-2:45pm with the event scheduled from 3-5pm. We ask that you stay until the end of the event at 5pm. Candy will be provided but please bring a starter stash.  Registration is required for all hosts and must be submitted by 10/29/21 at 10pm.   READ MORE

Trunk or Treat at Stamford Church of Christ

Stamford
Join the Stamford Church of Christ for this free event where preschool and elementary kids are invited to dress up and come with their families for fun games, hot dogs, bounce houses and trick or treating.  READ MORE

Noroton Presbyterian Church Trunk or Treat

Darien
Come one, come all!  Enjoy fellowship with the surrounding community in a safe fun-filled environment!  Fill your trunk with treats, decorate it (if you so wish), bring the kids and go trick or treating from car to car.  No crossing streets, long dark driveways and LOTS of fun!  Please keep the costumes and decorations appropriate and not scary.    READ MORE

Trick-or-Trunk at Masuk High School

Monroe
Trick-or-Treat around the parking lot. Come dressed up and ready to show off your decorated trunk! READ MORE

Trunk or Treat at United Methodist Church

Westport
Enjoy some free treats while giving back to the community. A suggested donation of 5 canned food items to benefit the pantry of Person to Person will be collected for each participating child. READ MORE

Trunk-or-Treat at Stew Leonard's

Norwalk
Children are invited to dress in their costumes and head to Stew Leonard’s in Norwalk to go trunk or treating in the parking lot! READ MORE

Trunk or Treat at the Goddard School

Danbury
Come in costume and join the Goddard School for the annual Trunk or Treat This event is rain or shine in the covered parking garage READ MORE

Fairfield Halloween Parades, Walks, and Runs

The Great Pumpkin Race & More

Newtown
Girls and boys of all ages are invited to build their own pumpkin racers! And decorate your pumpkins too! There will be food, music, entertainment, and a good time for all! READ MORE

Rowayton Community Center Halloween Celebration

Norwalk
Come in costume and explore the hay maze, take a pony ride, parade with your peers and enter the costume competition. READ MORE

Darien Halloween Parade and Magic Show with Amazing Andy

Darien
This parade through beautiful Downtown Darien is a colorful tradition for local preschoolers! Dress up your little ones and bring a bag for trick or treating at the doors of local merchants along the way from the Darien Fire Station to Tilley Pond.  READ MORE

Monster Dash 5K & 1 Mile Family Fun Run

Stamford
The Monster Dash 5k and 1 Mile Family Fun Run is a fun, costumed event with judging for best costumes! There’s a 1mile fun run for children and families. Post-race, there will be a great Halloween party, with festive music and Halloween games and great food. READ MORE
Pumpkins come in all shapes, sizes, and designs in Stratford. Photo courtesy of the Town of Stratford
Pumpkins come in all shapes, sizes, and designs in Stratford. Photo courtesy of the Town of Stratford

Fairfield Pumpkin Festivals, Carving, and Crafts

Tokeneke Elementary School's Pumpkin Carnival

Darien
The Tokeneke Pumpkin Carnival is a  favorite fall activity, offering something spooky and fun for children both big and small as Tokeneke Elementary School transforms into a Halloween-themed haunted house and amusement park. READ MORE

Wolfpit Pumpkin Festival

Norwalk
Come join Wolfpit Elementary School for a day of family fun activities including games, rides, arts & crafts and a basket raffle!  New this year, come check out the Marketplace with local craft and gift vendors.  Don’t miss out on the petting zoo, pony rides and hayride too!  Food trucks and seasonal baked goods will be available.  READ MORE

Stratford's Great Pumpkin Festival

Stratford
This celebration of autumn and Halloween will include a traditional costume parade and contest, a pumpkin carving contest, community booths and more.  READ MORE

Spooktacular Java Jam

Norwalk
Bring your little ghost or goblin to a SPOOKTACULAR Java Jam filled with halloween arts and crafts. READ MORE

Pumpkin Patch Party

Stamford
Head over to Bethany Church for the annual Pumpkin Patch Party! Games + crafts, donuts + cider, bouncy house and more! READ MORE
Boo at the Zoo. Photo by Ally Noel
Boo at the Zoo. Photo by Ally Noel

Spooky Halloween Events and Activities

Trick or Treat on Heckscher Farm

Stamford
Put on your Halloween costume and head over to Heckscher Farm where you can follow the paths to find the "trick or treat" stations located around the farm. READ MORE

Haunted Corn Maze at Wells Hollow

Shelton
Wells Hollow Creamery dares you to take a stroll through their Haunted Corn Maze. Don't forget to bring a flashlight, it gets dreadfully dark in the corn maze at night! READ MORE

Halloween on the Green

Fairfield
Join the fun at the  annual “Halloween on the Green” on the Museum Commons nearby the Historic Town Green. This family event will feature trick-or-treating, giveaways, displays in the historic buildings, a Food Truck Alley, a bounce house and other kid-friendly games.   READ MORE

Ridgefield Halloween Street Festival

Ridgefield
Local merchants, including the Ridgefield Library will open their doors to Ridgefield's trick-or-treaters.  READ MORE

Halloween Spooktacular at the New Canaan Nature Center

New Canaan
Get into the Halloween spirit by joining us for this spooktacular celebration, NCNC-style. Learn about and meet some fiendish friends who remind us of All Hallows Eve (spiders, snakes, owls, & more), enjoy making some creepy crafts, and roast a marshmallow while sharing spooky stories around a cackling (erm, we mean crackling) campfire! Top off the evening with our one-of-a-kind jack-o-lantern experience and you will be destined to have a dreadfully wicked evening!  READ MORE

Spooktacular! at the Discovery Museum

Bridgeport
A spooky time at the Discovery Museum. Guests will experience STEM Team Punkin' Chunkin', spooky science, mythology planetarium shows, Mad Science demonstrations, games, crafts, and more. The day will be filled with spooky activities and fun for the entire family.  READ MORE

Family Creep Fest at Westport Historical Society!

Westport
Embrace your scary side and start the spookiest month of the year off with a fright at Family Creep Fest!  READ MORE

Halloween Hayride Spooktacular

Norwalk
A family friendly hayride that runs through October 31. No reservations necessary. READ MORE

Ghouls in the Garden

Cos Cob
Join Greenwich Botanical Center 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.  READ MORE

The Enchanted Castle

Fairfield
The Enchanted Castle is a family friendly event where kids and parents walk through the entire Burr Homestead together. Each room is decorated with a different “Fairy Tale” theme, including Cinderella, The Little Mermaid, Beauty and the Beast and Aladdin. Besides awesome decorations kids will enjoy the live characters who will tell their stories.   READ MORE

Monster Mash at Stepping Stones Museum for Children

Norwalk
Stepping Stones is putting on a BOO-tiful night of tricks and treats jam-packed with family fun. Come and experience a wickedly-cool performance from the kookiest and spookiest of all mad scientists, Dr. Diabolical! Along with his lab assistant Frau Inga and his “right hand man” Lefty, the Doctor makes hilarious and macabre mayhem.  READ MORE

Hoot and Howl at the Darien Nature Center

Darien
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. READ MORE

Boo at the Zoo

Bridgeport
A spooktacular afternoon that’s a longstanding family tradition! Enjoy a DJ and music, special Halloween activities in the Kathy Brady Education Center, story-times, cool critters, and seasonal treats for sale! Guaranteed to delight and fright all those who pass through. Costumes encouraged! READ MORE

Places featured in this article:

Redding Community Center
Noroton Presbytian Church
United Methodist Church of Westport and Weston
The Goddard School (Danbury)
Tokeneke Elementary School
Fairfield Museum and History Center

About the Author

Ally Noel
Ally Noel has lived in Connecticut for over two decades. Before becoming a parent, she worked as an Educational Technology Specialist, helping schools and teachers integrate technology into learning. Now, she’s all about discovering the best family-friendly adventures, activities, and hidden gems. Share your tips, questions, or just say hi at ally@mommypoppins.com, and follow along for family fun at @mommypoppinsct.
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