Guilford Halloween Events

Guilford Halloween 2025

What to Expect This Halloween in Guilford!

Guilford halloween welcomes families to the town green and Whitfield Park with trick-or-treat parades, lantern walks, and historic ghost tours. Local harborside parks and the high street host pumpkin festivals, haunted walks, and seasonal craft fairs near the harbor.

Find the best Halloween events in Guilford this year!

Top Halloween Events In and Around Guilford

  1. Essex Steam Train & Riverboat Fall Foliage Ride (Essex)
  2. Bishop's Fall Festival
  3. Tracks of Terror Halloween Train Ride (Essex)
  4. Bishop's Fall Festival
  5. Bishop's Fall Festival
  6. Essex Steam Train & Riverboat Excursions (Essex)
  7. The Mayer Center Fear-Not Halloween Fun Day (Essex)
  8. Lyman Orchards Pick Your Own Season (Middlefield)
  9. Corn Maze & Cider Donut Harvest Music Festival (Middlefield)
  10. Trail of Terror (Wallingford)

🎃 Explore all 10+ featured events below!

Guilford Halloween Events

Guilford Family-Friendly Fall Activities (5)

A miniature autumn harvest scene with toy wagons filled with pumpkins and apples, set amongst corn stalks and pumpkins.
Details
📍 Guilford, CT, US
(2.8 mi from Guilford)

Bishop's Fall Festival

Unique Connecticut pizza-themed corn maze

When

Saturday, August 30, 2025

Event Details

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

Event Description

Celebrate the season at Bishop's Fall Festival, a beloved annual event featuring classic autumn fun with a unique Connecticut pizza twist. Wander through a massive 3.5-acre corn maze, pick your own apples, and enjoy a dedicated kids' activity area with slides and games. Select days offer delightful wagon rides and a variety of food trucks.

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fall_festivalfamily_friendlypumpkin_patchcorn_mazeapple_orchard
⭐ Best For: Families and autumn enthusiasts
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Three cartoon children are smiling and holding pumpkins in a pumpkin patch. The children are standing behind a basket filled with pumpkins, and there are rows of pumpkin plants in the background.
Details
📍 Guilford, CT, US
(0.6 mi from Guilford)

Bishop's Fall Festival

Expansive orchard with pick-your-own produce and fruit wines

When

Monday, September 1, 2025

Event Details

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

Event Description

Experience the vibrant autumn season at Bishop's Fall Festival, set against the picturesque backdrop of their expansive orchard. This beloved event offers a chance to pick your own seasonal produce, explore a bustling farm market filled with fresh goods, and sample unique fruit wines from their on-site winery. It's a perfect destination for family fun and embracing the spirit of fall.

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fall_festivalfamily_friendlypumpkin_patchharvest_festivalapple_orchard
⭐ Best For: Families, couples, fruit and wine enthusiasts
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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.
Details
📍 Guilford, CT, US
(2.8 mi from Guilford)

Bishop's Fall Festival

New Haven Pizza-themed 4-acre corn maze

When

Saturday, August 30, 2025

Event Details

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

Event Description

Bishop's Fall Festival offers a quintessential autumn experience with apple picking, a unique New Haven Pizza-themed corn maze, and a vibrant pumpkin patch. Families can enjoy a wide array of activities, including jump pads, a corn pit, and pedal carts, alongside scenic wagon rides. Savor seasonal treats from the Cider Hut and explore the Big Red Barn for local favorites.

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fall_festivalpumpkin_patchcorn_mazefamily_friendlyapple_orchard
⭐ Best For: Families and groups seeking autumn activities
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Two people wearing hats sit on a boat, looking at a steam train passing by on the water. In the background, there are buildings and trees.
Details
📍 Essex, CT, US
(15.0 mi from Guilford)

Essex Steam Train & Riverboat Excursions

Historic steam train and riverboat connection.

When

Saturday, May 10, 2025

Event Details

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

Event Description

Step aboard a vintage steam train for a scenic 12-mile narrated journey through the Connecticut River Valley. Enhance your experience with an optional riverboat cruise, offering unique views of historic landmarks. Choose your comfort with Coach or First Class seating on this memorable excursion.

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family_friendlytrain_rideriverboatfall_festivalcommunity_event
⭐ Best For: Families, history enthusiasts, scenic travelers
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A young girl and an older woman, possibly grandmother and granddaughters, are sitting in the open trunk of a car, decorating pumpkins. The older woman wears a festive Halloween hat. The scene suggests a fun autumn activity.
Details
📍 Essex, CT, US
(13.6 mi from Guilford)

The Mayer Center Fear-Not Halloween Fun Day

Sensory-friendly and not-so-scary Halloween fun for the community.

When

Saturday, October 18, 2025

Event Details

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

Event Description

Join The Mayer Center for a FREE and public Fear-Not Halloween Fun Day! This sensory-friendly event offers a not-so-scary experience with trunk-or-treat, face painting, and craft activities. Costumes are highly encouraged for this delightful community gathering.

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family_friendlytrick_or_treatface_paintingcommunity_eventnot_so_scary_halloween
⭐ Best For: Families with young children
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Guilford Haunted Experiences (1)

A miniature red steam train with a young girl in the driver's seat chugs along a track through a spooky forest at night, illuminated by glowing jack-o'-lanterns and a large, hazy moon.
Details
📍 Essex, CT, US
(15.0 mi from Guilford)

Tracks of Terror Halloween Train Ride

Spooky train ride through the Connecticut River Valley

When

Thursday, October 2, 2025

Event Details

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

Event Description

Prepare for a spine-chilling adventure on the Tracks of Terror, an immersive Halloween experience. This event begins with a captivating movie short that sets the stage for a heart-pounding train journey through the darkened Connecticut River Valley. Navigate a brief, eerie maze before boarding the train for a ride you won't soon forget. It's a Halloween experience unlike any other, perfect for those seeking a thrilling night out.

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haunted_attractionhaunted_trainhalloween_festivalcommunity_eventfamily_friendly
⭐ Best For: Thrill-seekers, halloween enthusiasts
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Guilford Other Halloween Activities (1)

A group of people ride on an open-air train through a scenic landscape during autumn, with vibrant orange and yellow foliage surrounding them.
Details
📍 Essex, CT, US
(15.0 mi from Guilford)

Essex Steam Train & Riverboat Fall Foliage Ride

Historic steam train and riverboat combination excursion

When

Saturday, May 10, 2025

Event Details

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

Event Description

Embark on a breathtaking journey through the vibrant autumn colors of the Connecticut River Valley aboard the historic Essex Steam Train. This unique experience offers a choice between a scenic 1-hour train excursion or a more immersive 2.5-hour train and riverboat combination. Select weekends even feature rides in a charming caboose for an unforgettable adventure.

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fall_festivalharvest_festivalfamily_friendlycommunity_eventhayride
⭐ Best For: Families, couples, history enthusiasts
See Full Details →

Near Guilford

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
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 12.6 miles from Guilford
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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
👻👻👻👻👻 💰 $ 🎃🎃🎃🎃🎃
📏 12.6 miles from Guilford
See Full Details →
See all 5 events in New Haven →

Meriden Halloween Events

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
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 14.2 miles from Guilford
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Three cartoon children stand in a pumpkin patch with many small pumpkins and green vines surrounding them.
Middlefield
Details

Lyman Orchards Pick Your Own Season

Nationally recognized pick-your-own farm with diverse seasonal produce.
💰 $$ 🎃🎃🎃🎃🎃
📏 14.2 miles from Guilford
See Full Details →
See all 6 events in Meriden →

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
👻👻👻👻👻 💰 $$$ 🎃🎃🎃🎃🎃
📏 17.1 miles from Guilford
See Full Details →
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
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 23.8 miles from Guilford
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Cheshire Halloween Events

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.
Cheshire
Details

St. Peter's Community Pumpkin Patch

Cheshire's beloved "Pumpkin Church" community tradition
👻👻👻👻👻 💰 $ 🎃🎃🎃🎃🎃
📏 18.5 miles from Guilford
See Full Details →
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.
Prospect
Details

Prospect Scarecrow Contest

Community scarecrow decorating event
👻👻👻👻👻 💰 FREE 🎃🎃🎃🎃🎃
📏 21.3 miles from Guilford
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See all 3 events in Cheshire →

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.
👻👻👻👻👻 💰 $ 🎃🎃🎃🎃🎃
📏 20.2 miles from Guilford
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A family dressed in Halloween costumes, including a pumpkin suit, a witch hat, and a fairy dress, are smiling on a beach with a horse and carriage in the background.
Milford
Details

Boo Fest By the Beach

Trick-or-treat stops throughout Walnut Beach Arts & Business District
👻👻👻👻👻 💰 $ 🎃🎃🎃🎃🎃
📏 21.5 miles from Guilford
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See all 3 events in Milford →

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 🎃🎃🎃🎃🎃
📏 21.2 miles from Guilford
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A smiling Black man and a young Black girl stand in a sunlit cornfield, surrounded by tall green corn stalks. The man wears glasses and a blue denim shirt, and the girl wears denim overalls over a striped shirt.
Shelton
Details

Wells Hollow Creamery Flashlight Maze

"It's a Bug's Life" themed corn maze
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 22.7 miles from Guilford
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See all 4 events in Shelton →

Stratford Halloween Events

Two cartoon women dressed as witches are smiling and holding pumpkins on a street decorated for Halloween. The woman on the left has white hair and an orange witch hat, while the woman on the right has dark hair and a purple witch hat.
Milford
Details

Walnut Beach Halloween Parade

Free ice cream for costumed attendees
👻👻👻👻👻 💰 FREE 🎃🎃🎃🎃🎃
📏 21.8 miles from Guilford
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A terrifying alien creature with sharp teeth and claws lunges towards three people running away in a dimly lit, red-lit building.
Stratford
Details

Fright Haven Haunted House

Over 20,000 sq. ft. of indoor scares across two main attractions.
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 23.7 miles from Guilford
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See all 3 events in Stratford →

New Britain Halloween Events

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.
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 23.9 miles from Guilford
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Glastonbury Halloween Events

A happy couple and their dog are driving in a car filled with pumpkins, with autumn trees visible outside the windows.
East Hampton
Details

Pumpkintown U.S.A.

Whimsical Pumpkinhead characters in themed village and forest settings.
👻👻👻👻👻 💰 $ 🎃🎃🎃🎃🎃
📏 22.9 miles from Guilford
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Montville Center Halloween Events

Three people in Victorian-era costumes are gathered around an open book in a dimly lit, ornate library, suggesting a theatrical or historical reenactment.
East Haddam
Details

William and James – A Ghost Story at Gillette Castle

Live theater inside the historic Gillette Castle
👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃
📏 16.5 miles from Guilford
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Last updated: 10/9/2025