It was All Hallows’ Eve in the town of Windy Hollow, tucked away in a holler in the hills of Eastern Kentucky. And you should also be aware that things ran a little differently there, but different wasn’t always a bad thing. 

You see, each October, a patch of bluegrass sprouted up by the dirt road leading into town. And on that grass popped up a vine of the plumpest pumpkins anyone had ever seen. Most would take first prize at any county fair, but the folks of Windy Hollow had discovered their real worth.

Lean in close now, and don’t repeat this to a soul: those pumpkins brought magic to those parts! You heard me right—magic! Everyone kept quiet about it. It was a secret only for their small town. 

The folks would roll their wagons and wheelbarrows to cut a pumpkin loose from the vine to take home with them. And on All Hallows’ Eve, they’d carve it up, plop a candle inside, and go to bed, eager as the beavers downstream for what the morning would bring. 

The next morning, as the sun peeked over the hills, the pumpkin would disappear, replaced by burlap bags of seeds for the farmers and maybe some jugs of moonshine for those who enjoyed the spirits. Mommas would snatch up the fresh vegetables for their stews and fabric to make new clothes. And the younguns, well, they were the happiest of all, receiving toys and candy to tide ‘em over ‘til Christmas. 

Well… all except one little boy. 

Billy lived alone with his momma in a shack so small it went unnoticed by the rest of the town. It sat back from the dirt road, on a spot of land that sagged lower than the rest. Pa had died a few years back, and Momma fell ill after that. Billy thought maybe her broken heart was what made her sick, so Billy stayed home and took care of her. They never had a pumpkin on their slanted porch, for it was too far for him to walk by himself, and he knew Momma wouldn’t take a liking to him asking for charity. 

Billy wasn’t the only one who felt left out, though. Back in that same pumpkin patch I told you about earlier, there was one small pumpkin named Willy, still stuck on the vine. He was well, best I just say it—a lil lopsided. His left side sagged, making him look kinda sad. And so the other folks passed him by for the bigger, rounder ones. 

Oh, Willy pouted for a bit, seeing he was the only one who hadn’t been picked, but then he decided to take matters into his own hands, that is, if he had hands. He’d find a porch on his own to sit on. So don’t you know that lil lopsided pumpkin mustered all his strength and rocked back and forth until he snapped plumb free of the vine. His stem twisted to the left with a few wiry tendrils sticking this way and that away (not helping his appearance). But no matter, Willy was free. Warming in his gooey insides, he began his wibbly-wobbly roll down the dirt road toward town. 

As he rolled passed house after house that already had a pumpkin on its porch, his hopes started to crumble. Maybe there would be no place for him after all. Worst of it was when he rolled through a cow patty, then had to bumpity bump to find a puddle to wash off in. If he knew one thing, he knew no one wanted a smelly pumpkin on their porch. Then, he saw it—a faint light so small that maybe it was a firefly. Curious, he bobbled along the bumpy earth where the path wasn’t quite so worn, until he saw it wasn’t a firefly after all, but a light in a tiny window of a shack—with no pumpkin on its porch!  

Meanwhile, inside, Momma crossed the floor with slow, doddering steps, her wheezing growing louder with each step. Billy tucked her in bed and kissed her cheek. “Happy All Hallows’ Eve.” She forced a smile, patted his cold cheek, and rolled over before he could see the tears in her tired eyes.

Billy hopped on his adjacent mattress by the window and blinked twice at what he saw. The most perfect pumpkin he could imagine sat outside the window on the porch. 

Willy looked up into the widest eyeballs he’d ever seen on a small face in the window, then the face disappeared. The front door creaked as it swung open, and before he knew it, the boy swept him up and hugged him so tightly he feared he might pop. 

“You are the most perfect pumpkin in the whole world!” hollered Billy. 

Willy blushed blood orange. Billy set him back on the porch, then ran inside and returned with a dull kitchen knife. He proceeded to poke and cut, doing his best he could to give Willy a bright and spooky smile. It came out crooked but just right for Willy. 

After tucking himself back into bed, Billy took one last look out the window at his precious pumpkin. While he slept, visions of candy corn danced in his head. Long after the fall wind blew the candle out, lil lopsided Willy glowed on that slanted porch, so happy to have found Billy. 

The next morning, Billy rushed out the door and froze. Willy was gone. In his place sat a pile of brightly wrapped candies, a wooden train set, and a pair of boots with no holes in sight. There was a stack of firewood, a hammer and nails, and also a mason jar of golden liquid labeled “For Momma”. 

Ma sipped from the jar while Billy happily played with his train, and wouldn't you know, color returned to Momma’s pale cheeks. By the next week, Momma was up and about, feeling her oats again. 

Oh my goodness, how things changed over the next year around that crooked little shack. Momma took to cooking again, making soups and baking the apple pies Billy remembered from before she got sick. Billy was growing fast and fixed the hole in the porch where he liked to play with his train. 

A distant neighbor, the Watkins family, noticed the smoke from their chimney and investigated, knocking on their door. They became friends, and Momma baked them pies while Mr. Watkins kept them in plenty of firewood and fixed the flapping shingles on their roof.

At night, after settling in bed, Billy would sometimes look out his window and whisper to the empty porch, “Thank you, Willy.” 

Then the morning finally came when Billy saw the first colored leaf fall and flutter against the window. “It’s time, isn’t it, Momma?”

Momma followed his eyes and set down her spoon, smiling. “Reckon it is, Billy. Let’s go see what pumpkin that patch has for us this year.”

From that October and every one after, Billy and Momma strolled along that long dirt road to the pumpkin patch. They’d patiently wait for the other folks to take their pick, then they’d happily take home whichever was left. For that was the perfect lil pumpkin for them.