Halloween Side Quests

Spooky things to do with friends, after dark and with kids, each with a mission, steps and a kit list. Pick one for this October.

Pick one for me

Halloween is the one night a year everyone agrees to be a little strange in public. These side quests use it: carve your friends’ faces into pumpkins, build a costume from a thrift store in 45 minutes, walk the neighborhood as a decorations critic, or chase a real local ghost story back to its first newspaper report.

Each card links to a full guide with steps, time and what to bring. Most need nothing you can’t find in a kitchen drawer or a thrift store.

Halloween With Friends

Give the party a mission: everyone carves a pumpkin portrait of someone else, or draws a secret character and has 45 minutes and $20 in a thrift store to become it.

Pumpkin Portrait Night - Social & Community quest

Pumpkin Portrait Night

Wait, is that pumpkin wearing my face?

Gather your friends, swap photos and carve each other's faces into pumpkins. You trace a printed photo straight onto the skin, then scrape and cut the shapes. On Halloween, you light them all up on the porch and watch your best friend's grin start glowing orange.

About 3 hoursFamilyGear from $23
Beginner
View Quest
Pumpkin Portrait Night
Thrift Store Costume Roulette - Social & Community quest

Thrift Store Costume Roulette

Who will you be by coffee time?

Grab a few friends, pull a random character out of a hat, and race through a thrift store with $20 and 45 minutes to become them. Then everyone walks to a cafe in full costume, where the reveal happens over hot chocolate and a lot of laughing.

2–3 hoursDate nightSupplies from $6
Beginner
View Quest
Thrift Store Costume Roulette
Tabletop Firepit Night - Creative Arts quest
Editor's pick

Tabletop Firepit Night

Pull up a chair, the marshmallows are almost gold

Gather your favorite people around a little tabletop fire and spend an evening building s'mores. You'll toast marshmallows to a glossy gold, press them between chocolate and graham crackers, and invent flavors nobody at the table saw coming.

2+ hoursFamilyGear from $70
Beginner
View Quest
Tabletop Firepit Night
Host an Improv Game Night Parlor - Social & Community quest

Host an Improv Game Night Parlor

Say yes to the silliest idea in the room

Clear the living room floor, invite six to eight friends over, and spend two to three hours playing short improv games. You'll pass invisible sounds around a circle, throw yourselves into instant scenes, and laugh at the weird choices nobody saw coming. No acting experience needed.

2-3 hoursFamilySupplies required
Beginner
View Quest
Host an Improv Game Night Parlor

Spooky Walks After Dark

October is the month to walk at night with a purpose: score the street’s decorations, trace a local legend to the spot it happened, or read the oldest stones in a cemetery while it’s still light.

Haunted House Critic Night - Social & Community quest

Haunted House Critic Night

Grab a clipboard. The ghosts are waiting for their reviews.

Grab your favorite people and a printed scorecard, then walk your neighborhood after dark judging every Halloween display you pass. Who has the creepiest skeleton? The best fog machine? At the end, your crew picks a winner and sneaks a handmade Best in Street award onto their doorstep.

1–2 hoursFamilyGear from $15
Beginner
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Haunted House Critic Night
Local Ghost Story Detective - Social & Community quest

Local Ghost Story Detective

Brave enough to meet the ghost's first headline?

Grab a friend and pick a ghost story people in your town still whisper about. Then play detective at the library and hunt down the very first time a newspaper printed it. The best part comes at dusk: you read that old article out loud, right where it happened.

3 hoursFamilyFree
Beginner
View Quest
Local Ghost Story Detective
Old Cemetery Epitaph Hunt - Social & Community quest

Old Cemetery Epitaph Hunt

Who was here first? Let's go find out.

Grab a curious friend and head to an old cemetery for a gentle detective game. You'll hunt down the oldest stone, find the wordiest epitaph, then pick one name and follow it into old census pages until a real person steps out of the past.

2–3 hoursFamilyFree
Beginner
View Quest
Old Cemetery Epitaph Hunt
Street Light Portraits - Creative Arts quest

Street Light Portraits

Street lamps make better portrait lights than you'd think.

Grab a friend who's willing to be your model and head out thirty minutes after sunset, when the street lights flick on and the sky is still deep blue. You'll turn a plain sidewalk lamp into a portrait light and come home with photos that look like a film still.

2-3 hoursDate nightGear from $165
Intermediate
View Quest
Street Light Portraits

Halloween With Kids

Spooky, not scary: monster hunts in a pond, a lantern-lit walk, a trick-or-treat game card.

Pond Water Monster Hunt: Find the Beasts Living in a Single Drop - Nature & Outdoors quest

Pond Water Monster Hunt: Find the Beasts Living in a Single Drop

One jar of murky water. A surprising number of residents.

Grab a jar, a friend and an afternoon. You're going to scoop water from a pond edge, a birdbath and a ditch, then put single drops under a microscope and meet whatever lives in them. Spinning green balls. Darting specks. A see-through shrimp with a beating heart.

2 hours (30 min collecting, 90 min looking)FamilyGear from $37
Beginner
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Pond Water Monster Hunt: Find the Beasts Living in a Single Drop
True-Twist Ghost Story Relay - Social & Community quest

True-Twist Ghost Story Relay

Spooky all the way down, then it's true?

Grab a flashlight and a few friends, turn off the lights, and build a ghost story one sentence at a time. The catch: the last line has to be a real fact about your town, like the year the old mill burned or the name under the clock tower.

45–60 minutesFamilyGear from $15
Beginner
View Quest
True-Twist Ghost Story Relay
Halloween Jar Lantern Parade - Social & Community quest

Halloween Jar Lantern Parade

Trick-or-treating, but first, a glowing grand entrance.

Spend Halloween afternoon making glowing jar lanterns with your kids, then lead a ten-minute parade around the block as the sky turns dark. Picture orange tissue-paper pumpkins and wobbly ghost faces lit from inside, bobbing down the sidewalk in a line of costumes.

1.5 hoursFamilyGear from $23
Beginner
View Quest
Halloween Jar Lantern Parade

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Frequently Asked Questions

What are fun things to do on Halloween as an adult?

Give the night a format: a pumpkin-portrait carving party, a thrift-store costume roulette with friends, a walk scoring the neighborhood’s decorations, or a dusk visit to the site of a real local ghost story.

What can I do for Halloween instead of a party?

Go out with a mission. Trace a local legend back to its first newspaper report and visit the spot at dusk, or walk your neighborhood after dark as a decorations critic and leave a handmade award at the winner’s door.

What are cheap Halloween ideas?

Most quests here cost under $25: a thrift-store costume on a $20 limit, pumpkins and a paring knife, or a printed scorecard for a decorations walk.

Is it okay to visit a cemetery for Halloween?

Visit in daylight or at dusk, during posted hours, and treat it as history, not a haunted attraction: stay on paths, don’t touch or rub fragile stones, and give mourners space.