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🎃41 designs · Updated for 2026

Intermediate Classic Pumpkin Cutouts

Looking for intermediate classic pumpkin cutouts? You're in the right place. Print at 100% scale, tape it to your pumpkin, and poke through the lines with a pin.

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41 intermediate classic pumpkin cutouts

Preview the design and choose one that matches your carving experience.

Intermediate

Four Sails Above Three Waves

A pirate ship rides three rolling waves, its mast carrying four billowing sail panels and a small flag snapping at the top. The sails, hull, flag, and waves are all cut through, while the mast and yard lines are strips of rind left between the openings to hold the rigging together. Those mast strips make it a medium carve: cut the four sail windows one at a time, always slicing away from the mast strip so you never lever against it.

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Intermediate

Wink and Five Rounded Gaps

One eye is a jaunty upswept crescent wink while the other stays a wide triangle, set over a small diamond nose and a lopsided grin broken into five rounded gaps by chunky teeth. The eyes, nose, and mouth gaps are cut through, leaving the tooth shapes as attached skin between them. A medium carver should cut the five mouth gaps individually rather than one big mouth, which keeps every tooth solidly connected and the crooked smile intact.

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Intermediate

Triangle Eyes and Six Diamonds

This elevated take on the traditional face pairs slanted triangle eyes topped with thin brow slits, a triangle nose, and a deep zigzag grin, then adds three small diamond cutouts on each cheek for extra sparkle. Every element is pierced through the wall. The brow slits and little diamonds are what push it to medium; cut the big shapes first, then handle each diamond with a narrow saw, working point to point so they stay crisp.

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Intermediate

Witch on a Left-Brushed Broom

A witch in a pointed hat rides her broom across the pumpkin, cloak trailing and broom bristles brushed out to the left as one bold glowing silhouette. The entire figure is cut through as a single connected opening, so the drama comes from the outline rather than fine interior detail. For this medium carve, start with the big body mass and work outward, cutting the hat point and individual bristle tips last so the surrounding rind supports your blade the whole way.

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Intermediate

Seven-Rib Shell and Three Dots

A fan-shaped scallop shell spreads seven glowing ribs from a hinged base, crowned by three small round dots floating above like sea spray. Each rib is its own cut-through opening separated by strips of intact wall, so the shell keeps its elegant ridged look when lit. Cut the center rib first and work outward symmetrically, keeping the dividing strips at least a finger-width so the fan stays strong.

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Intermediate

Almond Eyes and Seven Teeth

A wide, low jack-o'-lantern face with sly almond-shaped eyes, a small triangle nose, and a long jagged mouth packed with alternating square teeth top and bottom. Everything is pierced through, and the horizontal layout suits squat, wide pumpkins. At medium difficulty the tooth row is the main work; cut the mouth's outer outline first, then remove the gaps between teeth one at a time so each block keeps support while you work.

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Intermediate

Left Wink and Six Cheek Wedges

A playful winking jack-o'-lantern: one big round open eye, one arched wink, a triangle nose, and a smiling mouth with blocky teeth, all framed by three thin whisker-like wedges slashed across each cheek. Every opening is cut through, and the six cheek wedges throw extra slivers of light. At medium difficulty, cut the large features first and finish with the skinny cheek slits, using a fine saw so each wedge tapers to a clean point.

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Intermediate

Seven Stars in a Winding Trail

Seven five-pointed stars of varying sizes wind down the pumpkin in a gentle S-curve, like a constellation trailing across the night sky. Each star is a full cut-through opening, so the finished lantern twinkles from every angle. Star points are where beginners slip, so cut each arm from the outer tip inward toward the center and let the cuts meet, which keeps all five points sharp on every star.

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Intermediate

Arched Eyes and Six Freckles

A vintage-style pumpkin face with tall arched eyes, a triangle nose, a gap-toothed smile, and six little freckle holes dotted across the cheeks. The eyes, nose, mouth, and freckles all cut through, and each eye keeps a rooted pupil tab attached at the bottom for old-fashioned character. Drill or poke the freckles first with a small round tool, and cut toward each pupil tab's base so those thin anchors survive.

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Intermediate

Five Stars Around a Crescent

A crescent moon anchors one side while five stars and a scattering of small round dot holes twinkle across the rest of the pumpkin like a busy night sky. Every element is cut through, and the pattern wraps wide, which suits a bumpy or warty pumpkin beautifully. The medium rating comes from the sheer count of pieces, so drill or punch the little dots first as reference points, then carve the stars and finish with the big crescent.

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Intermediate

Crescent Seven Stars Six Dots

A large crescent moon glows at the left while seven chunky five-point stars and six round dots scatter across the rest of the pumpkin like a full night sky. Every moon, star, and dot is pierced through, so the whole surface twinkles when lit. Space your cuts out as you go, alternating sides of the pumpkin, so the wall keeps its strength until the final star is freed.

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Intermediate

Moon with Five Stars and Dots

A large crescent moon anchors the center of the pumpkin while five stars and a sprinkling of small round holes orbit around it. Every element is pierced through the wall, so the finished carve reads as a glowing night sky from across the yard. Carve the crescent first since it is the largest opening, then add the stars, sawing each point from the tip toward the center for clean corners.

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