Chesapeake Unique & Unusual Halloween Events 2026

17 unique & unusual Halloween events in Chesapeake and nearby.

As Halloween approaches, Chesapeake and nearby towns host a spectrum of seasonal events. From family-friendly gatherings in Chesapeake itself to destinations like the Olde Towne Ghost Walk in Portsmouth, there are many ways to celebrate the season.

Consider events happening across the water, like the International Sand Sculpting Championship in Virginia Beach, or closer to home with local monster bashes. Information follows for these and other happenings.

All Unique & Unusual Halloween Events Around Chesapeake

Monster Fest

Chesapeake Free

Annual celebration of horror in film and literature marking 20 years.

Illustration of a Halloween town at night with glowing windows, pumpkins, floating ghosts and a witch flying past a full moon (Old Point National Bank Wicked 10K Weekend)

Old Point National Bank Wicked 10K Weekend

Virginia Beach 17 mi

Halloween 6.2-mile oceanfront race finishing on the Virginia Beach Boardwalk.

Suffolk Peanut Fest

Suffolk 19 mi $

Four-day festival featuring carnival rides, live concerts, demolition derby, and fireworks.

Illustration of friendly ghosts on small town rooftops with pumpkins and glowing windows as two witches fly past a full moon (Treasures of the Earth Gem, Mineral, & Jewelry Show - Virginia Beach - Fall)

Treasures of the Earth Gem, Mineral, & Jewelry Show - Virginia Beach - Fall

Virginia Beach 17 mi $

Features custom jewelry, crystals, geode cutting, and on-site gem appraisals.

Wicked Monster Mile

Virginia Beach 17 mi

Flat and fast evening mile race through the ViBe District.

Virginia Beach Ghost Tour

Virginia Beach 18 mi $$

Haunted walking tour revealing coastal legends along the Virginia Beach Boardwalk.

Illustration of striped market booths and pumpkin displays on a street with small clay figures under orange autumn trees (Bodacious Bazaar Fall)

Bodacious Bazaar Fall

Hampton 19 mi $

Three-day shopping extravaganza featuring vendors, wineries, and distilleries.

Illustration of white ghosts floating over houses with glowing windows and pumpkins, with a witch flying past a full moon (Howl-o-ween: Dog Day at the Zoo)

Howl-o-ween: Dog Day at the Zoo

Norfolk 8 mi $$

Costumed pups explore the zoo, featuring dog agility demos and scent trails.

Illustration of a small cottage with glowing windows, ghosts, jack o'lanterns and a black cat among bare trees at twilight (Hampton Horror Tours 2026)

Hampton Horror Tours 2026

Hampton 18 mi

A walking tour through Old Hampton and St. John's graveyard.

Illustration of a Halloween craft scene with clay kids, a friendly ghost, bats and glowing pumpkins under party bunting (Spooky Night Lights Fused Glass Class)

Spooky Night Lights Fused Glass Class

Suffolk 13 mi $

Create a personalized four-inch fused glass seasonal night light.

Illustration of glowing jack-o'-lanterns, candles and scattered seeds on a wooden table under string lights at dusk (Pumpkin Living Succulent Arrangement Workshop)

Pumpkin Living Succulent Arrangement Workshop

Virginia Beach 16 mi $$$

Design a living pumpkin centerpiece with homegrown succulents and no carving.

Illustration of a craft table with a glitter pumpkin, paint cups, a clay kid, a smiling ghost and a paper bat under bunting (Spooky Jellyfish Terrarium Workshop)

Spooky Jellyfish Terrarium Workshop

Virginia Beach 16 mi $$

Craft hanging jellyfish terrariums using air plants and Halloween decor.

Illustration of kids in costumes at a table with pumpkins, bowls of treats, and paper bats and bunting overhead (Intro to Jewelry Making - Halloween Edition with Jama Watts)

Intro to Jewelry Making - Halloween Edition with Jama Watts

Norfolk 6 mi $$

Hands-on workshop crafting necklaces, bracelets, and earrings with a Halloween aesthetic.

Illustration of two clay kids and cotton ghosts around a craft table with painted pumpkins, paint pots and paper bats (Fall into Floss: An Embroidery Session)

Fall into Floss: An Embroidery Session

Norfolk 6 mi $$

Create an embroidered autumnal scene with artist Jama Watts.

Ghost Trinket Dish Craft Class

Norfolk 7 mi $$

Decorate a ceramic ghost trinket dish with charms, paint, and glitter.

Illustration of small purple clay characters carving glowing jack-o'-lanterns on a wooden table with candles and seeds (Pumpkin Terrarium Workshop)

Pumpkin Terrarium Workshop

Virginia Beach 16 mi $$

Craft a miniature plant ecosystem inside a glass pumpkin vessel.

Spooktacular Halloween Cleanup

Suffolk 16 mi $

Costumed volunteers cleaning up downtown Suffolk

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Illustration of a sunny autumn lawn with pumpkins, hay bales, a small tent, a witch and costumed children under orange trees

Family-Friendly Fall Activities

1 of 34 Mystique Fall Festival Chesapeake

Community festival featuring food trucks, local vendor shopping, and salon demonstrations.

See all 34 family events →

Illustration of a Halloween party at dusk with a ghost above string lights, two witches by a table, and glowing pumpkins

Food, Drink, and Parties

1 of 19 Halloween Cookie Decorating Class Chesapeake

Hands-on sugar cookie decorating class with six cookies to take home.

See all 19 parties & tastings →

Illustration of a small haunted cottage with glowing windows, ghosts, pumpkins and a black cat under a big pale moon

Haunted Experiences

1 of 15 The 757 Ghosthunter Experience: Backbay's Brew House Virginia Beach

After-hours paranormal investigation using real ghost hunting equipment.

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Illustration of a small ghost and a jack-o'-lantern performing on a stage with red curtains, watched by a crowd at dusk

Movies, Theater, and Entertainment

1 of 5 Candlelight: Halloween Classics Portsmouth

Halloween classics performed by a string quartet by candlelight.

See all 5 shows & screenings →

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Frequently Asked Questions

How can we volunteer or participate in Halloween events in Chesapeake instead of just attending?

Community events run on volunteers, and signing up transforms the season: host a trunk at a trunk-or-treat, judge a costume contest, staff a festival craft table, or join a parade group. Sign-ups post in September through schools, libraries, and neighborhood groups, and shifts are usually two or three hours, leaving time to enjoy the event. Volunteering is also the best free ticket in town.

What should we wear on a ghost tour in Chesapeake?

Ghost tours are night walking tours, so dress for 60-90 minutes outdoors in October: real walking shoes for cobblestones and uneven sidewalks, a warm layer you'd want an hour after sunset, and rain gear when the sky is ambiguous, since most tours run in drizzle. Skip the flip-flops and the costume; hands-free is best for the dark stretches between stops.

How do we build a full Halloween day itinerary in Chesapeake?

Stack by energy curve: daytime farm or market while everyone's fresh, a late-afternoon rest and food stop, then the evening event, tour, show, or haunt, as the finale. Keep drive legs under 30 minutes between stops, book only the evening portion as a timed ticket so the day can flex, and end the night close to home, not across town.

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