Boomers & Gen X Celebrated Halloween In 7 Cool Ways Younger Generations Will Sadly Never Know

Written on Oct 28, 2026

Cool Ways Boomers & Gen X Celebrated Halloween Photo Editor: Arianna Jeret | Photo: Bruno Guerrero, Unsplash
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Baby boomers and Gen X know that no matter how much fun kids today have, their Halloweens will never include some of the experiences that made it such a magical time back in the day.

Sure, older generations may have had pillowcases full of candy (and sometimes boxes of raisins), but they didn't need expensive costumes to make the night special. Many of the homemade treats and mischievous pranks they excelled at are just a few of the Halloween joys that most younger people will sadly never know.

Baby boomers and Gen X loved celebrating Halloween in sweet ways younger generations probably won't get to experience: 

1. TP'ing houses with toilet paper

TP over trees and a house Susan Law Cain | Shutterstock

Was it kind to throw toilet paper over people's trees? Probably not. But boomers and Gen X didn't care. They lived in the moment with little regard for the future. Mischievous at heart, they would TP their neighbors' houses and blame it on getting into the Halloween spirit.

Sadly (for the kids, not for the neighbors), this tradition seems to have basically stopped. Parents nowadays are hypervigilant on Halloween. They don't want their kids to eat candy full of needles. Even if that's just an urban legend, parents don't care. That's why kids don't do Halloween pranks. Their parents' watchful eye keeps them from getting up to mischief.

RELATED: Gen Z, Millennials, Gen X & Boomers Have Different Ideas Of Appropriate Halloween Costumes

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2. Trick-or-treating without their parents supervising them

kids trick or treating without parents supervising Charles Parker | Pexels

Parents today are built different. They don't ignore their children or tell them, "Be back when the streetlights come on." Especially on Halloween, trick-or-treating without parents supervising is unheard of. In parents' eyes, Halloween is one of the most dangerous holidays.

But as the Marshall Project pointed out, researchers found no variations in the number or types of crime committed on Halloween. Still, that statistical fact won't stop parents from hovering. As parents become less trusting, the younger generation will never know what it's like to be unsupervised.

RELATED: 5 Spookiest Celebrations Around The World That Rival Halloween

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3. Bobbing for apples at Halloween parties

green apples being used for bobbing at halloween parties AngelaAllen | Shutterstock

Everyone has seen people bob for apples at state county fairs. While it might have gone out of style, bobbing for apples isn't a foreign concept for the younger generations. Bobbing for apples was originally a part of celebrating Samhain, a pagan holiday that predated Halloween.

Boomers and Gen X might've had a blast bobbing for apples, but parents nowadays find it way too unsanitary. Grossed out by the spit-filled water buckets, they'd rather skip this Halloween tradition than watch their kids take a go.

RELATED: 5 Things People Who Are Obsessed With Halloween Are Doing Right In Life That Everyone Else Usually Overlooks

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4. Using pillowcases to collect their mountains of candy

mountains of candy in trick or treat bucket Jaclyn Vernace | Shutterstock

Call them cheap, but back in the day when baby boomers and Gen X were growing up, parents weren't about to waste money on special Halloween buckets. It might've looked nice, but being frugal was the lifestyle back then. Instead, kids got creative, using their pillowcases to collect their mountains of candy.

Just because their parents weren't dropping a dime doesn't mean they had to suffer. If kids wanted to participate, they would use their pillowcase and leave. Sure, it's a little unsanitary if you don't wash the pillowcase first, but they didn't care. They drank water from a water hose. They'd be fine.

RELATED: Watch What Your Kid Does With Their Halloween Candy — It’s Basically A Personality Test For Future Success

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5. Wearing homemade costumes

two kids wearing homemade ghost costumes with sunglasses Anastasia Lashkevich | Shutterstock

Once again, parents were cheapskates back then. They weren't willing to spend money on a costume their kids would only wear for a couple of hours. Plus, way more kids had stay-at-home moms who knew how to sew and could create whatever costume they wanted.

Even if their moms weren't great with a sewing machine, boomers and Gen X got creative. With a little tape and a blanket, they made their own Halloween costumes. It might not have been as fancy as buying a costume, but they made it work. Unlike younger generations, they didn't need to spend money to have a good time. After all, experience matters more than the price tag. That's probably why Halloween was so elite back then.

RELATED: Ring Camera Catches Kids Taking Candy Out Of Their Halloween Bags To Refill An Empty Bowl On A Porch

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6. Receiving homemade treats from neighbors

candy apples homemade treats Misto Graphy | Shutterstock

Halloween wasn't only about candy, and kids back then didn't just come home with full-sized Milky Way bars. Boomers and Gen X also often got homemade treats from their neighbors.

While Halloween might be fading in popularity, it was a big deal back then. Neighbors didn't ignore each other and only show up once a blue moon. They formed close relationships and gave freely. That's probably why neighbors went all out. Making homemade desserts like candy apples was another way they could do something fun for their neighborhood.

RELATED: Mom Handing Out Cups Of Mac & Cheese And Ramen Instead Of Candy On Halloween — It’s The ‘Perfect Timing’ To ‘Be A Villager’

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7. Getting pennies while trick-or-treating

pennies on halloween Pixabay | Pexels

It might sound bizarre today, but getting pennies while trick-or-treating was fairly common back then. It started with some kids collecting spare change to help undernourished kids around the world. But over time, some people turned giving out pennies into a Halloween tradition.

That Halloween tradition has long since faded. While boomers and Gen X remember coming home with pennies, most younger people never got to experience this cool way of celebrating Halloween.

RELATED: Kids Who Grew Up In The 70s & 80s Experienced 9 Things That Made Halloween Feel Weirdly Magical

Marielisa Reyes is a writer with a bachelor's degree in psychology who covers self-help, relationships, career, family, and astrology topics.

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