Chesapeake Halloween - spooky scene with haunted house, jack-o-lanterns, ghosts, witches, and trick-or-treaters

Chesapeake Halloween 2025

See all Chesapeake Halloween happenings this year!

Chesapeake unveils Halloween 2025 around the Greenbrier area and Chesapeake City Park with eerie entertainment and Halloween thrills. The calendar fills with Halloween festivals, haunted experiences, family activities, pumpkin patches, and neighborhood trick-or-treat celebrations.

Find the best Chesapeake Halloween happenings this year!

Chesapeake Halloween

Chesapeake Family-Friendly Fall Activities

A diverse group of people enjoying a sunny autumn day at a pumpkin patch. In the foreground, a Black woman with curly hair and a plaid shirt smiles as she sits in a wagon, while an older white man with a kippah and glasses sits in front of her. The background features a large inflatable pumpkin, a bouncy house, and many pumpkins scattered across the ground, creating a festive atmosphere.
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Great Bridge Pumpkin Patch

Wednesday, September 17, 2025
📍 Great Bridge Pumpkin Patch
900 N Battlefield Blvd, Chesapeake, VA 23320
(2.5 mi from Chesapeake)

Event Details

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

Event Description

Discover a delightful fall experience at the Great Bridge Pumpkin Patch. This family-friendly destination offers a dedicated Pumpkin Patch Play Land, perfect for creating lasting memories. Kids can bounce to their hearts' content in the bounce houses and explore the charming pumpkin patch to find their ideal jack-o'-lantern.

pumpkin_patchfamily_friendlyfall_festivalkids_gamesbounce_houses
⭐ Best For: Families with young children
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Chesapeake Haunted Experiences

A group of figures in dark cloaks stand on a foggy, moonlit path lined with bare trees and stone archways, some holding glowing orbs or a jack-o'-lantern, creating a mysterious and eerie Halloween atmosphere.
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Great Bridge Terror Woods

Wednesday, October 1, 2025
📍 Great Bridge Terror Woods
900 N Battlefield Blvd., Chesapeake, VA 23320
(2.5 mi from Chesapeake)

Event Details

👻 Scare Factor: 👻👻👻👻👻
🎃 Family Friendly: 🎃🎃🎃🎃🎃
⚡ Energy: High

Event Description

Dare to enter the Great Bridge Terror Woods this October for a spine-chilling experience. This haunted attraction promises a terrifying journey through the woods, designed to test your courage and deliver unforgettable scares. Prepare for a night of frights and screams.

haunted_attractionhaunted_trailhaunted_foresthalloween_festivalcommunity_event
⭐ Best For: Thrill-seekers and horror fans
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Chesapeake Halloween Food, Drink, and Parties

Three adults, two women and one man, are smiling and enjoying glasses of red wine at an outdoor table in a park setting. A bottle of red wine and two glasses are on the table in front of them.
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Chesapeake Virginia Wine Festival

Saturday, October 11, 2025
📍 Chesapeake City Park
900 City Park Dr, Chesapeake, VA 23320
(3.6 mi from Chesapeake)

Event Details

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

Event Description

Uncork a good time at the 15th annual Chesapeake Virginia Wine Festival. Sample unlimited pours from over 20 Virginia wineries and explore international selections. Enjoy live music and chef-driven bites in a festive outdoor setting. This event supports local charities, making every sip count.

wine_tastingfood_truckscraft_beer_festivalcommunity_eventcharity_event
⭐ Best For: Wine enthusiasts and adults seeking a festive outdoor experience.
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Chesapeake Other Halloween Activities

Halloween event image for Monster Fest 20 - movies and theater entertainment themed
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Monster Fest

Saturday, October 4, 2025
📍 Chesapeake Central Library
298 Cedar Road, Chesapeake, VA 23322-5598
(3.9 mi from Chesapeake)

Event Details

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

Event Description

Dive into the world of horror at Monster Fest, an annual celebration of film and literature's darkest corners. This event brings together fans for a day filled with special guests, authors, a vibrant vendor market, and a thrilling costume contest. Experience live music and discover unique horror-themed merchandise.

horror_conventioncommunity_eventcostume_contestfamily_friendlyother
⭐ Best For: Horror fans, literature enthusiasts, families
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Halloween Near Chesapeake

Portsmouth Halloween

A group of people in hooded cloaks and witch hats stand on a cobblestone street lined with houses decorated for Halloween. Glowing jack-o'-lanterns are scattered throughout the scene, illuminated by streetlights and the full moon overhead.
Portsmouth
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Olde Towne Portsmouth Ghost Walk (Portsmouth)

📍 Trinity Episcopal Church
Oct 24, 2025
(4.7 mi from Chesapeake)
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Portsmouth Halloween Safe Trunk or Treat in Portsmouth
Portsmouth
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Portsmouth Halloween Safe Trunk or Treat (Portsmouth)

📍 Atlantic Union Bank Pavilion & Festival Park
Oct 25, 2025
(4.4 mi from Chesapeake)
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See all 4 events in Portsmouth →

Norfolk Halloween

Twisted Fairytales Halloween in Norfolk
Norfolk
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Twisted Fairytales Halloween (Norfolk)

📍 Waterside District
Oct 31, 2025
(5.3 mi from Chesapeake)
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Haunted Norfolk Tour in Norfolk
Norfolk
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Haunted Norfolk Tour (Norfolk)

📍 Downtown Norfolk
Oct 1, 2025
(5.4 mi from Chesapeake)
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Portsmouth Heights Halloween

Portsmouth Fall Festival in Portsmouth
Portsmouth
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Portsmouth Fall Festival (Portsmouth)

📍 Portsmouth City Park
Oct 4, 2025
(6.3 mi from Chesapeake)
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Suffolk Halloween

Cullipher Farm Fall Corn Maze in Suffolk
Suffolk
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Cullipher Farm Fall Corn Maze (Suffolk)

📍 Cullipher Farm
(16.6 mi from Chesapeake)
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Adult Halloween Monster Mash Ball in Suffolk
Suffolk
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Adult Halloween Monster Mash Ball (Suffolk)

📍 Suffolk Center for Cultural Arts
Oct 25, 2025
(16.6 mi from Chesapeake)
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South Suffolk Halloween

A smiling Black woman wearing a wide-brimmed hat and overalls stands in the foreground at an outdoor fair. In the background, people ride motorcycles and a striped tent with American flags is visible.
Suffolk
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Suffolk Peanut Fest (Suffolk)

📍 Suffolk Executive Airport
Oct 9, 2025
(18.9 mi from Chesapeake)
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Virginia Beach Halloween

Three cartoon characters in Halloween costumes stand in front of a large aquarium filled with fish. The character on the left wears a witch costume, the middle character wears a skeleton costume, and the character on the right wears a ghost costume. They are gathered around a table with pumpkins and candy, preparing for Halloween.
Virginia Beach
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Fins & Frights (Virginia Beach)

📍 Virginia Aquarium & Marine Science Center
Oct 17, 2025
(17.2 mi from Chesapeake)
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Four people are running away from a giant, glowing purple alien-like figure in a dimly lit room decorated with a large blue spiderweb.
Virginia Beach
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Haunted Hunt Club Farm Halloween Festival (Virginia Beach)

📍 Hunt Club Farm
Sep 26, 2025
(14.7 mi from Chesapeake)
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Hampton Halloween

A man wearing a straw hat and a plaid shirt is talking to a smiling woman in a blue jacket at a pumpkin patch. They are surrounded by many pumpkins, and in the background, there are farm buildings and trees with autumn leaves.
Hampton
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Bluebird Gap Farm Fall Festival (Hampton)

📍 Bluebird Gap Farm
Oct 18, 2025
(19.1 mi from Chesapeake)
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Two young women with stylized anime-like features, wearing headphones and backpacks, are looking at a tablet together in a crowded indoor setting with blurred background lights.
Hampton
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NekoCon 2025: Cy-Purr-Punk (Hampton)

📍 Hampton Roads Convention Center
Oct 31, 2025
(19.3 mi from Chesapeake)
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East Hampton Halloween

The Rocky Horror Picture Show - Classic Movie Nights in Hampton
Hampton
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The Rocky Horror Picture Show - Classic Movie Nights (Hampton)

📍 The American Theatre
Oct 31, 2025
(17.3 mi from Chesapeake)
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A man and a woman stand in a pumpkin patch with rows of pumpkins stretching into the distance, with a barn and cornfields in the background. Both are holding pumpkins and smiling at each other.
Cape Charles
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Shockley Farms Corn Maze and Pumpkin Patch (Cape Charles)

📍 Shockley Farms
(37.6 mi from Chesapeake)
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Newport News Halloween

A terrifying zombie with a chainsaw chases a person through an abandoned, overgrown subway car with orange lighting.
Williamsburg
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Busch Gardens Howl-O-Scream (Williamsburg)

📍 Busch Gardens Williamsburg
Sep 5, 2025
(37.7 mi from Chesapeake)
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Four cartoon children of diverse ethnicities sit on a wooden bench in a pumpkin patch, surrounded by pumpkins and festive orange lights, with hay bales and a cornfield in the background.
Toano
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Pumpkinville (Toano)

📍 Pumpkinville
(50.3 mi from Chesapeake)
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See all 9 events in Newport News →

View Our Interactive Map for More Events Around Chesapeake

Discover thousands of halloween across the country

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Halloween road trip adventure with spooky characters

Halloween Road Trips & Weekend Getaways

Worth the drive for more halloween near Chesapeake!

Richmond (82.8 miles) Tuckahoe (90 miles) Greenville (100 miles) Rocky Mount (101.4 miles) Wilson (115.6 miles) Waldorf (132.8 miles) Dale City (140.7 miles) Lake Ridge (143.7 miles) Alexandria (146.7 miles) Raleigh (147.7 miles)

Looking for more? Explore all Virginia Halloween →

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Our Process

With 20 years of experience, we use AI technology to build the most comprehensive list of halloween events.

Our goal is complete coverage—from major festivals to small community celebrations, ensuring you never miss anything happening in your area.

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