Pancake stack: three squat pumpkins, butter and syrup on topTan, brown, yellow. Each tan with a darker band at its edge; a yellow square by the top stem; brown drips below it.
Ballet tutu around the middle, ribbons crossed below itPink, white. A ruffled band of short pink strokes around the widest part; ribbon lines cross down to the base.
Loud necktie under a white collar, no face at allWhite, black, three brights. Collar points under the stem; a wide tie of clashing stripes down the middle rib.
Bath time: shower cap over the stem, foam around the basePink, white, black. A dotted cap painted down from the stem; white sponged foam up to a small happy face.
Crash landing: striped witch legs and a snapped broomBlack, purple, green, tan. Two striped legs point up at odd angles on the front; a broom in two pieces below.
Foamy grin with a toothbrush painted across itWhite, blue, black. A wide row of teeth under white sponged foam; a blue toothbrush crosses from one side.
Headphones over the top, mouth wide open in songBlack, red, white. A band crosses beside the stem to a round cup on each side; shut eyes, one big mouth.
Jogger: a red sweatband under the stem, sweat drops flyingRed, white, pale blue, black. A band around the shoulder; gritted teeth, puffed cheeks; blue drops off both sides.
Loud necktie under a white collar, no face at allWhite, black, three brights. Collar points under the stem; a wide tie of clashing stripes down the middle rib.
Pink hair curlers in rows over the top, a sleepy scowlPink, gray, black. Short curler rolls cross the ribs around the stem; half-shut eyes and a flat mouth below.
Protest sign: a painted hand holds up PAINT, DON'T CARVEWhite, black on bare orange. A square sign on a stick in one small hand; a stern frown and lowered brows below it.
Selfie: a painted arm holds a phone up to its own grinBlack, gray on bare orange. A grin on the front; one arm outlined around the side to a small gray phone.
Sunburned pumpkin with pale sunglasses marksRed, cream, black. Red all over except a cream sunglasses shape across the eyes; two dot eyes inside it.
Wet paint sign beside one smeared handprintWhite, black, one bright color. A hanging sign lettered WET PAINT; a handprint dragged sideways beside it.
Worried eyes looking down at a pumpkin pie recipe cardWhite, black. A recipe card low on the front, its first line 1 PUMPKIN; wide eyes above it look down.
Scariest, kept mild 12
Costume parade in silhouette around the middleBlack, yellow on bare orange. Small figures in hats, capes and sheets walk one way around; yellow lantern dots.
Dark burrow hole near the base, a long tail trailing outBlack, gray, pink. One round black hole low on the front; a thin tail curls out along the base; two eye dots inside.
Empty scarecrow post: a hat left on top, straw trailing awayTan, brown, yellow, black. A bare cross-post in front, a hat hung on it; yellow straw marks trail off around one side.
Gilt-framed portrait whose eyes look off to one sideGold, black, gray, white. An oval gold frame on the front; a pale stern face inside it; both pupils far to one side.
Raven perched below the stem, feathers drifting downBlack, gray on bare orange. One black bird in profile high on the front; four loose feathers fall along the grooves.
Sea serpent swimming through: humps rise and dip aroundDark green, yellow, navy. Navy coat; four arched humps around the middle, as if it dives in and out; a head in front.
Stairs winding around and up to one small lit doorBlack, gray, yellow. Black coat; gray steps spiral from the base to the shoulder; a yellow door beside the stem.
Stone gargoyle crouched under the stem, wings foldedThree grays, black. Sponged gray coat; a horned face and folded wings in darker gray; claws grip a ledge line.
Tentacles curling up from the base on every sidePurple, lilac, black. Black coat; thick arms rise from the base and curl at the tips; a row of pale suckers on each.
Three claw slashes painted as dark rips, pale at the edgesBlack, cream on bare orange. Three long slanted rips across the front, black inside, a thin cream rim on each.
Two eyes and two nostrils above a waterlineDark green, yellow, black. Murky green below a level line around the middle; just above it, two eyes and a snout.
Under the bed: a bedspread hem, two yellow eyes below itNavy, white, yellow, black. A scalloped bedspread edge around the middle; black below it; two small eyes low in front.
Cutest 12
Ballet tutu around the middle, ribbons crossed below itPink, white. A ruffled band of short pink strokes around the widest part; ribbon lines cross down to the base.
Blowing bubbles: a wand at the mouth, rings drifting upwardBlack, pink, pale blue, white. Shut eyes and a small pursed mouth; a pink wand; pale rings in rising sizes above.
Bookworm leaning out of a hole over a tiny open bookGreen, black, white, red. A dark hole on the front; a green worm with round eyes leans out above a small red book.
Bow tie and suspenders with two gold clipsRed, navy, gold. A red bow tie under a small smile; two navy straps run down from the shoulder to gold clips.
Counting sheep: shut eyes, three sheep jumping over the stemWhite, black, pale blue. Closed eyes low on the front; three woolly sheep in an arc over the top, numbered 1, 2, 3.
Hiccups: a startled face, HIC lettered three times up a ribBlack, white, pink. Round eyes and a small open mouth; HIC in capitals three times, smaller each time, toward the stem.
Hula hoop tilted around the middle, motion ticks beside itPink, yellow, black. One bright hoop painted at a slant all the way around; short curved ticks; a laughing face above.
Knitting its own scarf: two needles, stripes down the frontBlack, gray, two brights. A small smile; two crossed needles under it; a striped scarf runs down and around the base.
Looking up at one falling leaf, tongue out to catch itBlack, white, pink, red. Both eyes rolled up toward the stem; a small pink tongue; one red leaf painted just above.
Peekaboo: two mittens over the eyes, one eye peeking betweenRed, white, black. Two red mittens side by side high on the front; one round eye in the gap; a wide smile below.
Sash of round badges across the front, a proud small grinGreen, yellow, red, blue. A green sash from one shoulder to the base; six round badges on it, each a different picture.
Sitting in a teacup: a flowered cup around the lower halfWhite, blue, pink, black. A white cup with a handle and small flowers below the middle; a sleepy face above the rim.
Most original 12
Birdcage: a thin bar down every groove, a bird on a swingGold, yellow, black on a white pumpkin. Gold bars follow the grooves from stem to base; one small yellow bird inside.
Blueprint of a jack-o'-lantern in white lines on blueBlue, white. Blue all over; the face drawn in thin white outline, with measuring arrows and small notes.
Circuit board: green coat, silver tracks along the groovesDark green, silver, gold, black. Thin silver lines run down the grooves and turn at right angles; gold dots at the ends.
Crossword grid: black and white squares, PUMPKIN acrossWhite, black. A white panel of small squares on the front, some filled black; seven capitals lettered along one row.
Cutaway: half bare orange, half the seeds and strings insideCream, yellow, dark orange. A straight edge down one groove; past it, pale strings and rows of teardrop seeds.
Eye chart: one big letter on top, smaller on every row downWhite, black. A white panel on the front; a large P at the top; each row below smaller, the rows spelling out PUMPKIN.
Front page: a headline, a photo box, columns of gray linesWhite, black, gray. A white page shape on the front; PUMPKIN WINS in block capitals; ruled lines stand in for print.
One giant fingerprint looping across a white pumpkinBlack on a white pumpkin. Close curved lines loop around one center on the front and spread to both sides.
Paint by number: outlined shapes, only half of them filledBlack, four colors. Thin outlines with a small number in each shape; one side colored in, the other left blank.
Peeling corner: the orange curls back to show a night skyNavy, white, pale orange. A curled flap painted at one shoulder; under it, navy with stars; a shadow below the curl.
Pixel face: eyes and a grin built from black squaresBlack on bare orange. A grid chalked on first; each feature filled in square by square, its edges stepped.
Stained glass: black lines, one jewel color in every paneBlack, red, blue, green, amber. Panes fitted between the grooves; thick black lines painted last over each join.
Best group or pair 12
Big fish, small fish: three in rising sizes, mouths openBlue, green, orange, white. One fish painted side-on per pumpkin, each open mouth aimed at the smaller one ahead.
Four steps on four pumpkins: bare, sketched, half done, doneWhite chalk, black, three brights. The same face on each: nothing, chalk lines, half the paint, all of it.
Painter and portrait: one in a beret, one a framed pumpkinBlack, gold, red. A face under a painted beret on the first; a gold frame around a small pumpkin picture on the second.
Pancake stack: three squat pumpkins, butter and syrup on topTan, brown, yellow. Each tan with a darker band at its edge; a yellow square by the top stem; brown drips below it.
Pool rack: fifteen minis as numbered balls in a triangleSeven colors, white, black. A number disc on each: 1 to 7 solid, 9 to 15 with one wide stripe, the 8 black.
Rock, paper, scissors: one hand sign on each of threeBlack, white on bare orange. A fist, a flat hand and two spread fingers, each drawn large; set close in a row.
See, hear and speak no evil: three faces, hands painted onBlack, white on bare orange. Hands over the eyes on one, at the sides of the next, over the mouth on the last.
Spot the difference: one face painted twice, five changesBlack, white, two brights. Two pumpkins of one size with the same face and hat; five small details changed on one.
Stack of three: bottom face straining, the top one wavingBlack, white, red. Gritted teeth and red cheeks at the bottom; a calm face in the middle; a grin and a wave above.
Stadium wave: five in a row, arms rising toward the middleBlack, white on bare orange. One grin on all; arms down at the ends, half up on the next, straight up in the middle.
Walking the pet: a big pumpkin holds a leash to a miniBlack, red on bare orange. A hand and a red leash painted on the big one; a collar and a happy face on the mini.
Winners' podium: gold, silver and bronze on three pumpkinsGold, silver, bronze, blue. A medal on a blue ribbon painted on each front; set on boxes, the gold one highest.
How it works
These pumpkin painting ideas to win a contest are 60 no-carve designs, 12 for each prize. Every one is a single idea, made to read from across a room.
Read the full guide
Painted pumpkin contest ideas, prize by prize
Funniest holds sight gags, such as Sunburned pumpkin with pale sunglasses marks. Scariest stays mild enough for a school hall, as Gilt-framed portrait whose eyes look off to one side does. Most original plays on the pumpkin itself, as Cutaway: half bare orange, half the seeds and strings inside does.
Painted pumpkin decorating contest ideas for a group
Every entry under Best group or pair is made of more than one pumpkin. A class can paint Pool rack: fifteen minis as numbered balls in a triangle between them. Two friends can split Painter and portrait: one in a beret, one a framed pumpkin.
Questions and answers
What are some pumpkin painting contest winning ideas?
No list can promise a ribbon. These go for one clear idea that can be said in a few words: Blueprint of a jack-o'-lantern in white lines on blue, or Stack of three: bottom face straining, the top one waving.
What are cute pumpkin painting ideas for a contest?
The cutest ones are doing something. Peekaboo: two mittens over the eyes, one eye peeking between takes three colors. Sitting in a teacup: a flowered cup around the lower half and Bookworm leaning out of a hole over a tiny open book are fuller pictures.
What is a funny pumpkin painting idea for a contest?
One whose gag shows from the back of the room. Worried eyes looking down at a pumpkin pie recipe card is a joke only a pumpkin can tell. Crash landing: striped witch legs and a snapped broom needs no face.
What are scary pumpkin painting ideas for a school contest?
The Scariest group hints and never shows: Two eyes and two nostrils above a waterline, or Stairs winding around and up to one small lit door. None has blood or a weapon.