If you’ve ever visited Essex, CT, during Halloween, you know we don’t hold back when it comes to celebrating the spookiest time of the year. From intricately carved pumpkins and lively costume parades to family-friendly festivals and spooky fun for all ages, Halloween in Essex is a tradition that just keeps getting better. Inspired by my 3rd-grade teacher’s annual pumpkin display on their family farm, this Halloween spirit is alive and well in our community, and it’s best showcased at the Ivoryton Village Pumpkin Parade and Festival.
The 25th Annual Ivoryton Pumpkin Festival – A Day Full of Fall Fun
Mark your calendars for Saturday, October 25, 2025, because you don’t want to miss the 25th Annual Ivoryton Pumpkin Festival! This festive gathering brings over 1,500 visitors to the Ivoryton Village Green for a FREE day of autumn and Halloween traditions. There’s something for everyone—from live music and hayrides to pumpkin carving and sweet treats.
Start the day with a Pre-Festival Pumpkin Carving Party hosted by Bushy Hill Nature Center. Join fellow pumpkin enthusiasts from 9:30 am to 12:30 pm, where you can carve your own masterpiece to display at the lighted Pumpkin Stroll. Then, head over to the Ivoryton Village Green to find your perfect spot for the Great Pumpkin Challenge. Families, community groups, and local businesses are invited to bring their carved pumpkins between 9 am and 4 pm. Let’s see who can create the most impressive jack-o’-lantern display!
Costume Parade and Trunk or Treat: A Halloween Parade for the Kids
The fun continues with the 4th Annual Costume Parade, perfect for children ages 12 and under. Register online for your chance to snag some Pumpkin Festival swag, and march down Main Street at 4 pm in your spooky, silly, or sweet costume. Plus, this year, the Ivoryton Village Alliance is sponsoring a Trunk or Treat, making it even easier to load up on candy!
After the parade, stick around for live music from The Federation and face painting by The Painted Smile—a perfect way to add those last-minute touches to your costume. Don’t forget to stop by the cookie decorating station, hosted by Tri-Town Youth Services, or enjoy a horse-drawn hayride around the green.
Spooky Surprises and Haunted Happenings
For those craving a little mystery, The House of the Triple Moon will be offering Tarot Card readings at the Ivoryton Library Association from 4:30 pm to 6:30 pm. If you’re in the mood for a good scare (but not too scary), take a haunted hayride around the village, and admire the beautifully lit pumpkins during the Pumpkin Lighting, starting at 4 pm.
More Fall Fun in Essex: FestiFall and Grace & Haven’s Halloween Fun
The Halloween magic doesn’t stop there! Be sure to check out FestiFall in downtown Essex, featuring a scarecrow competition along Main Street, promotions from local merchants, and a photo booth and kids’ games at Grace & Haven. It’s a wonderful opportunity to shop local and get into the fall spirit. There are even Broom & Hat Making Workshops and a Hocus Pocus Themed Brunch aboard the Essex Steam Train to round out the festive fun.
Join the Essex, CT Halloween Celebration
Halloween in Essex is more than just a holiday—it’s a community celebration filled with creativity, fun, and a dash of spookiness. Whether you’re taking part in the Ivoryton Pumpkin Festival, strolling through the scarecrow-lined streets of Essex, or enjoying a Halloween-themed brunch, there’s something for everyone.
Grab your costumes, carve your pumpkins, and get ready to make lasting memories with your family and friends. We can’t wait to see you there!
