Cheshire Halloween Events

Cheshire Halloween 2025

What to Expect This Halloween in Cheshire!

Cheshire halloween centers around Cheshire Park and the town green with haunted trails, pumpkin festivals, and family-friendly evening events. Explore South Main Street for cider stands, craft booths, and parade-style trick-or-treating.

Find the best Halloween events in Cheshire this year!

Cheshire Halloween Events

Cheshire fall_festival (1)

Two young women, one with red hair and the other with dark curly hair, are sitting in a pumpkin patch surrounded by many pumpkins. The woman with red hair is holding a small pumpkin stem and looking down at it, while the woman with dark curly hair is holding a large pumpkin and smiling.
Details
📍 Cheshire, CT, US
(0.7 mi from Cheshire)

St. Peter's Community Pumpkin Patch

Cheshire's beloved "Pumpkin Church" community tradition

When

Monday, September 1, 2025

Event Details

👻 Scare Factor: 👻👻👻👻👻
💰 Budget: $
🎃 Family Friendly: 🎃🎃🎃🎃🎃
⚡ Energy: Low

Event Description

Experience the charm of Cheshire's "Pumpkin Church" as St. Peter's Episcopal Church transforms into a vibrant pumpkin patch each September and October. This cherished 20-year tradition offers a fantastic opportunity to select the perfect pumpkin while supporting indigenous growers and local charities. Enjoy family-friendly fun, including pumpkin painting and games, making it a quintessential fall outing.

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⭐ Best For: Families, community members, charity supporters
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Cheshire Haunted Experiences (1)

A group of people are running down a dark hallway with red lighting, being chased by a large, monstrous creature with sharp teeth and claws.
Details
📍 Plantsville, CT, US
(5.1 mi from Cheshire)

Haunt on Eden

Terrifying haunted attraction experience.

Event Details

👻 Scare Factor: 👻👻👻👻👻
💰 Budget: $$
🎃 Family Friendly: 🎃🎃🎃🎃🎃
⚡ Energy: High

Event Description

Prepare for a night of frights at Haunt on Eden, a premier haunted attraction. They offer a terrifying experience designed to thrill and scare visitors. For a more family-friendly option, check out their 'Trunks and Treats' event. Explore their gallery to see past scares and join their team if you dare.

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⭐ Best For: Thrill-seekers and halloween enthusiasts
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Cheshire Other Halloween Activities (1)

A cheerful scarecrow with a wide smile and rosy cheeks stands in the foreground, dressed in denim overalls and a green shirt, holding a bundle of straw. An elderly woman in a light-colored jacket faces the scarecrow, gesturing with her hands, while other people and autumn decorations like pumpkins and fall foliage are visible in the blurred background.
Details
📍 Prospect, CT, US
(3.5 mi from Cheshire)

Prospect Scarecrow Contest

Community scarecrow decorating event

When

Friday, September 5, 2025

Event Details

👻 Scare Factor: 👻👻👻👻👻
💰 Budget: FREE
🎃 Family Friendly: 🎃🎃🎃🎃🎃
⚡ Energy: Low

Event Description

Residents of Prospect are invited to showcase their creativity by designing and displaying unique scarecrows. This event celebrates the fall season and community spirit, offering a charming visual display for all to enjoy as they explore the town.

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⭐ Best For: Families, community members
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Near Cheshire

Meriden Halloween Events

Two cartoon-like figures with mustaches are running down a forest path, surrounded by lush green foliage and trees. The figure in the foreground is wearing a teal shirt and ripped pants, with a surprised expression and his arm outstretched. The figure behind him wears an orange shirt and dark pants, with a determined look.
Wallingford
Details

Trail of Terror

Outdoor haunted trail with "Coven of the Rotted" theme
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 5.2 miles from Cheshire
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A cartoon character with a white body and no facial features walks through a pumpkin patch with tall corn stalks on either side under a cloudy sky.
Middlefield
Details

Lyman Orchards Pick Your Own Pumpkins

Over 275,000 lbs of pumpkins grown annually
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 9.6 miles from Cheshire
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See all 6 events in Meriden →

Waterbury Halloween Events

Three women in theatrical costumes are singing into microphones on a stage, with whimsical bird props flying above them.
Waterbury
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Hocus Pocus Live!!! 2025

Live musical parody of the cult classic Hocus Pocus film
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 7.4 miles from Cheshire
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A man and a woman run away from a giant robot in a greenhouse filled with purple fog and plants.
Waterbury
Details

Nightmare's Gate Haunted Attraction

Immersive haunted attraction with themed scare zones
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 7.8 miles from Cheshire
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See all 4 events in Waterbury →

Bristol Halloween Events

Three cartoon characters, two children and one adult, ride in a Halloween-themed amusement park ride with spooky buildings and pumpkins in the background.
Bristol
Details

Phantom Fall Fest at Lake Compounce

Five haunted houses including the all-new Project Nightmare maze
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 9.0 miles from Cheshire
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New Britain Halloween Events

Three cartoon children in Halloween costumes stand in a grassy yard with pumpkins. The child on the left wears a dark jacket and orange hood, the middle child wears a witch's hat and purple and gold dress, and the child on the right wears a pink hooded cape and holds a glowing jack-o'-lantern.
CT 06051
Details

Halloween Trick or Treat Safe Zone

Safe trick-or-treating at over 30 downtown businesses
👻👻👻👻👻 💰 FREE 🎃🎃🎃🎃🎃
📏 12.9 miles from Cheshire
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A young woman with long dark hair and an orange scarf smiles brightly as she rides a carousel at an amusement park on a sunny day.
Berlin
Details

The Berlin Lions Agricultural Fair

Classic agricultural fair with diverse entertainment and vendors.
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 12.9 miles from Cheshire
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New Haven Halloween Events

Two cartoon children, a girl and a boy, stand on a cobblestone street in front of a haunted house on Halloween night, surrounded by playful ghosts and spooky decorations.
New Haven
Details

Ghosts of New Haven Haunted Ghost Tours

Explore New Haven's haunted history and spectral legends
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 13.8 miles from Cheshire
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Two skeletons dressed as sugar skulls, adorned with flowers and makeup, sit at a bar holding drinks, with a vibrant, neon-lit street scene in the background.
New Haven
Details

2025 New Haven Halloween Bar Crawl

Day of the Dead themed bar crawl with festive decorations
👻👻👻👻👻 💰 $ 🎃🎃🎃🎃🎃
📏 13.8 miles from Cheshire
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See all 5 events in New Haven →

Middletown Halloween Events

Three cartoon characters in a spooky, purple-hued haunted mansion decorated for Halloween. A girl dressed as a witch in the center is flanked by a man with wild white hair and a ghost-like figure, all appearing to dance.
Middletown
Details

Haunted Halloween Bash

Spooky costume party at historic Wadsworth Mansion
👻👻👻👻👻 💰 $$$ 🎃🎃🎃🎃🎃
📏 12.3 miles from Cheshire
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A smiling young woman wearing a plaid shirt and scarf stands in a pumpkin patch with a tractor and tents in the background.
Cromwell
Details

Fair Weather Growers Fall Festival & Corn Maze

16-acre farm transformed for fall fun
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 14.8 miles from Cheshire
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Shelton Halloween Events

A cartoon illustration of a young girl and an older man standing in a pumpkin patch during autumn. The girl holds a pumpkin, and both are smiling. The background features a tent, more pumpkins, and colorful fall foliage.
Seymour
Details

Seymour Pumpkin Festival

A community tradition since 1965 supporting local organizations.
👻👻👻👻👻 💰 FREE 🎃🎃🎃🎃🎃
📏 11.1 miles from Cheshire
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Three people run in terror through a graveyard at night, illuminated by a giant, glowing purple spider looming overhead.
Shelton
Details

Legends of Fear Haunted Hayride & Trail

Two terrifying attractions: Haunted Hayride and Hallow Trail.
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 18.3 miles from Cheshire
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See all 4 events in Shelton →

Wethersfield Halloween Events

A young girl in a red dress holding a lantern walks through a foggy graveyard at night, illuminated by hanging lanterns and carved pumpkins, under a full moon.
Hartford
Details

Hallowed History Lantern Tour

Lantern-led historical tour with character actors
👻👻👻👻👻 💰 $ 🎃🎃🎃🎃🎃
📏 18.8 miles from Cheshire
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Guilford Halloween Events

Two farmers in a pumpkin patch, one holding an apple and smiling at the camera, with a barn and rows of pumpkins in the background.
Guilford
Details

Bishop's Fall Festival

New Haven Pizza-themed 4-acre corn maze
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 16.5 miles from Cheshire
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A miniature autumn harvest scene with toy wagons filled with pumpkins and apples, set amongst corn stalks and pumpkins.
Guilford
Details

Bishop's Fall Festival

Unique Connecticut pizza-themed corn maze
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 16.5 miles from Cheshire
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See all 3 events in Guilford →

Milford Halloween Events

A group of children in Halloween costumes are participating in a race, with pumpkins and bats decorating the scene. The main focus is on two girls running towards the viewer, one dressed as a witch and the other in a Batman-themed costume.
Milford
Details

14th Annual Milford 5K Trick or Trot Run/Walk

Charity 5K run/walk supporting local homeless services.
👻👻👻👻👻 💰 $ 🎃🎃🎃🎃🎃
📏 20.5 miles from Cheshire
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Last updated: 10/9/2025