Part 2: 30 Bikers Dressed as Princesses, Superheroes and Bunnies Rolled Into a Broke Neighborhood on Halloween — What They Did at Each Door Wrecked Me
Thirty Harleys rolled into the poorest trailer park in our county on Halloween night.
The men riding them weren’t wearing leather.
They were wearing tutus.
When I finally understood why, I had to sit down on the curb and stop filming.
My name is Denise Holloway.
I’m a second-grade teacher at McKinley Elementary in Ashland, Kentucky.
Forty-three years old. Nineteen years in this town.
My husband Mike rides with the Ironwood MC — a small local club out of 13th Street.
Most of them are welders. Mechanics. A few veterans. A couple of grandfathers.
Good men. Not a 1% club. Nothing fancy.
Last October 31st, at exactly 6:02 p.m., thirty of those men left their clubhouse on Harleys.
They rode up the two-mile hill.
Into Foothill Ridge.
Foothill Ridge is forty-two trailers and fifteen small houses on three gravel streets.
No sidewalks. No streetlights past Maple.
And on Halloween — not a single porch light gets turned on.
Because nobody up there can afford to buy candy.
The kids in Foothill Ridge don’t trick-or-treat in their own neighborhood.
They walk two miles down the hill. To the nicer streets.
They come home with pillowcases that have to be split four ways.
One of my former students told his mother two years ago, very matter-of-factly:
“Next year I’m not going. It makes the little kids cry when we come home and there’s only enough for one each.”
That sentence is what started this.
My husband heard about it at the dinner table.
He put his fork down.
He looked at the wall for a long moment.
Then he got up and called the club president — a sixty-one-year-old retired trucker they call Preacher.
He said six words.
“Brother. I gotta tell you something.”
Between February and October, thirty grown men quietly did three things.
They each bought six full bags of full-size candy. Out of their own pockets.
They each got fitted for a costume that Preacher’s wife hand-sewed in her basement.
And they each trained — I am not making this up — to be able to walk trailer to trailer for three hours in full princess regalia over a leather cut.
When they rolled into Foothill Ridge that night, a 320-pound biker named Bulldog was wearing a pink sequined tutu and a plastic tiara.
A six-foot-five diesel mechanic named Tiny was in a full Belle gown.
Preacher himself was in a Captain America suit he refused to take off over his leather cut.
There was a Spider-Man. A Chewbacca. A pink bunny. Three Wonder Womans.
Thirty Harleys. Thirty costumes. Thirty pumpkin buckets.
And on the very first porch — a pale green single-wide belonging to a seventy-three-year-old widow named Miss Iris who had not opened her door on Halloween in nine years — a 320-pound man in a tutu got down on one knee.
What he did next made that woman sit down on her own porch step and cry for ten minutes.
And on the inside of his pumpkin bucket, underneath the plastic rim where nobody was supposed to see it, he had written six words in black sharpie.
Six words that were on every single bucket that night.
But what made me sit down on the curb that night wasn’t Miss Iris crying on her porch step.
It was six words written in black sharpie on the inside of Bulldog’s pumpkin bucket — six words he thought nobody would ever see.
And I didn’t know, until he flipped his bucket over to show me later, that all thirty buckets that night carried the exact same six words — in the exact same man’s handwriting.
The Ironwood MC was founded in 1998 in a garage on 13th Street in Ashland.
Seven Vietnam-era veterans who wanted a place to drink coffee and ride.
They are not a 1% club.
They are welders, electricians, diesel mechanics, one dentist, two retired cops, a Baptist deacon, and my husband.
They are also, to a man, men who grew up poor.
Mike grew up in a trailer two miles from Foothill Ridge.
His mother raised him and his brother on a waitress’s wages.
He has told me — exactly once, in twenty-one years of marriage — about the Halloween he was eight years old.
He put a pillowcase over his head.
He told the neighbors he was a ghost.
Because his mother couldn’t afford a costume.
Two houses gave him candy. The third house told him to go home.
He walked back to the trailer in the dark.
He told his mother he’d had a great time.
The club president is a man named Hollis Ward.
Road name Preacher. Sixty-one. Six-foot. Retired long-haul trucker.
The son of a Baptist minister.
Preacher’s wife Loretta makes most of the costumes.
She has a sewing room in her basement. She has been sewing for the club’s Halloween ride for eleven years.
Yes. Eleven years.
This is not the first time they’ve done it.
It is the seventh neighborhood.
Every October, Preacher and three senior brothers sit down with a map of Boyd County.
They pick the block that needs it most that year.
They don’t advertise. They don’t post about it. They don’t take donations.
Every brother buys his own candy. Minimum six full-size bags.
Out of his own pocket.
That is the rule. Preacher set it in 2014.
“If we’re not paying for it ourselves, we’re not really giving anything,” he told me once at a barbecue. “We’re just passing somebody else’s money through our hands. That ain’t what this is.”
When Mike called Preacher about Foothill Ridge that night after dinner, Preacher listened for four minutes without interrupting.
Then he said, “Brother. That’s this year. Tell your wife.”
Between that phone call in February and Halloween on October 31st, thirty grown men quietly went to work.
Loretta made six tutus.
Eight capes.
Three full-body animal suits.
And one Belle gown that fit a 47-year-old diesel mechanic named Tiny, who is six-foot-five and weighs three hundred and ten pounds.
A brother named Skipper — an ex-Army combat medic — learned to hot-glue rhinestones onto a plastic tiara from a YouTube tutorial.
He ruined two hot-glue guns in the process.
A brother named Doc — a literal dentist — ordered a Spider-Man suit off Amazon.
He tried it on in the club bay.
He could not get it off without help.
Three brothers started taking weekly walking laps around the clubhouse in October.
Because, in Preacher’s words:
“You can’t trick-or-treat for three hours in full princess regalia if you ain’t in shape, brothers.”
I know all of this because Mike came home every Thursday that fall.
Sat at the kitchen table.
Told me what the weirdest grown men in Kentucky were doing with their spare time.
By mid-October, every brother had his costume. His candy budget. His assigned block.
Ten trailers each. Thirty brothers. Three hundred pounds of candy.
Nobody in Foothill Ridge knew they were coming.
The ride left the Ironwood clubhouse at 6:02 p.m. on October 31st.
It was already dark.
Forty-six degrees.
Thirty Harley-Davidsons rolled down 13th Street.
Turned onto Carter.
Crossed the river bridge.
Went up the two-mile hill to Foothill Ridge.
If you have never seen thirty Harleys ridden in formation by men dressed as Disney princesses, Spider-Man, the Hulk, Belle, a pink bunny, Wonder Woman, a Ninja Turtle, and a man in a homemade Chewbacca suit that Loretta spent forty-one hours constructing — I can tell you this.
The noise is unchanged.
The visual is not.
People came out on their porches along 13th Street to stare.
A woman dropped her cigarette.
A gas station attendant at the Marathon on Carter ran out to his parking lot.
He filmed the entire procession.
Later posted it to TikTok.
Got 3.1 million views before the club asked him to take it down.
He did. They’re private people.
They parked in a long row on the gravel at the corner of Maple and Spruce.
The entrance to Foothill Ridge.
They killed thirty engines.
And for about ten seconds, the only sound on that hill was thirty leather cuts settling and thirty pairs of combat boots hitting gravel.
Then Preacher — in a full Captain America costume over his leather cut, because he would not take the cut off — lifted his plastic shield and said, quietly:
“Boys. Ten trailers each. You go slow. You kneel down if the kid is little. You compliment every single costume even if they don’t have one. Nobody gets skipped. Nobody. Move out.”
I was there.
I had followed them up in my car.
Preacher had asked me to document it for the club’s private records.
I parked at the top of Spruce.
Stood on the curb with my phone.
Started filming.
The first trailer Bulldog walked up to belonged to Miss Iris.
Miss Iris Pennington is seventy-three years old.
Black. Widowed. Retired school cafeteria worker.
Grandmother of one of my former students.
Her husband Ernest died in 2015.
Her only son was killed in a workplace accident at a lumber yard in 2016.
Since then, she has lived alone in a pale green single-wide with a small iron porch and a storm door she does not open between dusk and dawn.
She had not handed out Halloween candy in nine years.
Not because she didn’t want to.
Because she could not afford it.
And could not bear to stand in the dark of her own living room with the lights off pretending she wasn’t home.
Bulldog — real name Marcus Reed, fifty-two, 320 pounds, Black, former Army, diesel engine rebuilder — walked up her gravel path.
Pink sequined tutu over his jeans.
Pink plastic tiara bobby-pinned into his gray hair.
Plastic wand in one massive scarred hand.
Pumpkin bucket full of full-size Snickers and Reese’s and Kit Kats in the other.
He did not ring the bell.
He knocked. Gently. Three soft taps with one knuckle.
She did not come to the door.
He waited.
He knocked again. Same three taps.
Through the storm door — I could see this from the curb, forty feet away — a light came on inside.
A small shuffling.
Miss Iris in a housecoat peered through the blinds.
She saw a 320-pound Black man in a princess tutu standing on her porch holding a pumpkin bucket.
She opened the door.
Miss Iris stepped out onto her porch in her housecoat and slippers.
She put one hand on the porch rail to steady herself.
She said, “Baby. What on earth.”
Bulldog got down on one knee.
Slowly. The way a very large man kneels.
He held up the pumpkin bucket.
He said, in a voice I heard clearly across the cold night air:
“Ma’am. Happy Halloween. Would you please do me the honor of taking some candy?”
Miss Iris looked at the bucket.
She looked at him.
She looked at the twenty-nine other costumed bikers scattered up and down her street.
Each one on a porch.
Each one doing the same thing.
She sat down on her porch step.
Just sat.
Right down.
She started to cry.
Not a polite cry.
The kind of cry that comes out of a woman who has been holding something in for nine years.
Bulldog did not get up off his knee.
He set the pumpkin bucket down on the porch beside her.
He took his plastic tiara off his head.
He put his big scarred hand gently — so gently — on Miss Iris’s shoulder.
He said:
“Ma’am. You ain’t gotta give me nothing. I’m the one giving you candy. This is for you. Please.”
Miss Iris looked up at him through tears.
She said:
“Baby, I don’t have any kids coming tonight. I ain’t had a kid come to this door in nine years. They know I don’t have nothing to give.”
Bulldog said:
“Ma’am. There’s about forty kids comin’ up this street in the next hour. We already told ’em. And every one of ’em is gonna knock on this door. And you’re gonna have this bucket to give out. That’s why I’m here.”
Miss Iris stared at him.
He stood up — three hundred and twenty pounds on a bad knee, in a pink tutu.
He walked back down her gravel path.
He turned at the mailbox.
Gave her a small wave with the plastic wand.
Headed to the next trailer.
Miss Iris Pennington sat on her porch step with a full bucket of candy in her lap.
She cried for about ten minutes.
Then she went inside.
Turned on every light in that trailer.
Dragged her rocking chair onto the porch.
When the first wave of Foothill Ridge children came up the street twenty minutes later — mostly in handed-down costumes, a few in garbage bags with eye-holes cut in them — Miss Iris Pennington was sitting on her porch.
Bucket on her lap.
A smile on her face I had not seen since her son died.
Every child who came to that porch got candy from her.
Not from the bikers.
From her.
The bikers made sure of it.
They walked alongside the kids.
They pointed at her door.
They said things like “That house right there, buddy. Miss Iris got the good stuff tonight.”
Ninety-four children went to Miss Iris’s door between 6:30 and 8:30 that night.
She handed out candy to every one.
At one point — I filmed this — a little girl in a Moana costume hugged Miss Iris around the legs and said, “Thank you, grandma.”
Miss Iris had to hold the rail to stay standing.
At 8:47 p.m., with the ride almost over, Bulldog came and sat on the curb next to me.
Still in his pink tutu.
He was out of breath.
His tiara was crooked.
His pumpkin bucket was empty.
I asked him, “Marcus. Why this?”
He didn’t answer for a long time.
Then he said:
“Miss Denise. When I was seven years old, my daddy was doing time and my mama was working three jobs. I went trick-or-treating with a pillowcase and no costume. One lady on Beech Street slammed the door in my face and called me a thief. I walked home in the dark crying. And I told my mama I’d had a great time.”
He looked down at his giant scarred hands.
Still holding the plastic wand.
“I’m fifty-two years old. I own my own shop. I got a Harley and a house and a good wife. And every October I still think about that little boy walking home with no candy. Every year.”
He looked up at Miss Iris’s porch.
She was still handing out candy to a little boy dressed as a pumpkin.
“Tonight ain’t just for these kids, Miss Denise. I mean, it is. But it ain’t just for them. It’s for the seven-year-old me. And the seven-year-old Mike. And the seven-year-old Preacher. Every man on this street tonight was once a kid who didn’t get candy. That’s why we’re here.”
He wiped his face with the back of his wrist.
The pink sequins on his tutu caught the streetlight.
“A kid in a tutu don’t look scary, Miss Denise. That’s the whole point. These kids up here — they been taught to be scared of men like us. Tonight we ain’t scary. Tonight we’re princesses.”
Later that night, after the last children had gone in, after the bikers had gathered back at the corner of Maple and Spruce, after thirty Harleys had fired up again and rumbled back down the hill —
Preacher stayed behind.
He went up Miss Iris’s gravel path.
Climbed onto her porch.
Sat down on the step next to her rocking chair.
I walked over because I could not help myself.
He said, “Ma’am. You got anything left in the bucket?”
Miss Iris — eating her first Snickers of the night — held out the bucket.
Preacher took one Kit Kat.
He unwrapped it.
Ate it on her porch step next to her rocking chair.
Two old strangers on a Halloween porch in the poorest neighborhood in the county.
He said, “Miss Iris. You gonna open your door next Halloween?”
She looked out at the empty street.
She said, very quietly:
“Baby. I’m gonna open this door every Halloween till I die.”
Preacher nodded.
He stood up.
He tipped the Captain America shield at her like a hat.
He said, “Then we’ll be back.”
That was last October.
This year, Preacher told me at our Fourth of July barbecue, the Ironwood MC is going back to Foothill Ridge.
Not every year — they rotate — but they voted at club meeting in May.
This year is an exception.
Because in June, Miss Iris called Preacher’s wife Loretta.
Somehow got the number from my sister.
She asked if there was any way the bikers could come back to her street one more time.
She said she had saved up.
Ten dollars a month from her Social Security.
For eight months.
She had bought her own bucket of candy.
She wanted to hand it out alongside them this year.
Loretta called Preacher.
Preacher called Mike.
Mike came home and told me.
He sat at the kitchen table for a long time after he told me.
Then he said:
“Babe. I gotta go buy more candy this year.”
I still have the video I filmed that night.
I watch it sometimes on my phone. In bed. When I can’t sleep.
Miss Iris on her porch step.
Bulldog on one knee in a pink tutu.
Ninety-four children going up that path.
A woman handing out candy for the first time in nine years to a little girl dressed as Moana.
On the inside of the pumpkin bucket Bulldog carried up Miss Iris’s path that night, underneath the plastic rim where nobody could see it, he had written one sentence in black sharpie.
I only found out because he showed me later at the clubhouse.
Six words.
“FOR THE KID WHO WENT HOME.”
Every biker’s bucket had the same six words.
Same man’s handwriting.
Preacher had written them on every single bucket the week before.
Thirty buckets.
One sentence.
Six words.
He had not told any of them he was doing it.
They found out on the ride.
If this story moved you — follow the page. The Ironwood boys ride again this October. And Miss Iris will be on her porch.
