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14 Jack and Sally Painted Pumpkin Ideas for a Fun Halloween

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If you’re a Halloween and “The Nightmare Before Christmas” fan, painting pumpkins with Jack and Sally is a quirky way to show off your creative side. Each pumpkin adds a bit of that spooky charm to your home, making decorating for the season actually fun.

One or two painted pumpkins on a tabletop, featuring a Jack Skellington face with a bat-shaped bow tie and a pumpkin with colorful patchwork designs.

With these Jack and Sally painted pumpkin ideas, there’s bound to be something that sparks your imagination. Whether you lean toward simple or want to get lost in the details, there’s a design here for everyone.

Classic Jack Skellington black-and-white face pumpkin

Close-up of one or two painted pumpkins on a table, featuring black-and-white faces inspired by Jack Skellington, with vibrant colors and detailed designs.

A plain white pumpkin can become Jack Skellington’s signature spooky face with a dash of black paint for those big eyes and a stitched-up smile. It’s easy, but the effect? Always a little bit haunting.

Sally Patchwork Dress Inspired Pumpkin Painting

Close-up of one to two pumpkins painted with colorful patchwork designs inspired by a patchwork dress, displayed on a clean tabletop with soft natural light.

Try painting your pumpkin a pale blue, then layering on colorful patchwork shapes—just like Sally’s dress. Honestly, you can get as wild as you want with the patterns.

Sally holding a pumpkin basket painted on pumpkin

Two pumpkins painted with colorful designs of Sally and Jack from The Nightmare Before Christmas placed on a tabletop.

Paint Sally in her patchwork dress, gently holding a little pumpkin basket. It’s a sweet detail that just feels right for Halloween.

Jack with bat bow tie painted on pumpkin

One or two painted pumpkins on a tabletop, featuring a Jack Skellington face with a bat-shaped bow tie and a pumpkin with colorful patchwork designs.

Add Jack’s famous bat bow tie beneath his grinning face. It’s a tiny detail, but it makes the whole thing pop.

Pumpkin with Jack and Sally hugging painted scene

One or two pumpkins painted with a detailed scene of Jack and Sally hugging.

Paint Jack and Sally hugging on your pumpkin for a heartwarming vibe. There’s just something soft and magical about it.

Jack with pumpkin patch surrounding him painting

Close-up of one or two painted pumpkins inspired by Jack and Sally, surrounded by a small pumpkin patch on a tabletop.

Let’s paint Jack Skellington right in the middle of a playful pumpkin patch. Imagine curly pumpkin vines twisting around and a bunch of cute jack-o’-lanterns scattered at his feet—it’s got that perfect Halloween vibe, doesn’t it?

Glow-in-the-Dark Jack Pumpkin

A table decorated with glowing carved pumpkins, candles, and autumn flowers, creating a Halloween-themed centerpiece near a window.

This pumpkin shines brightly with glow-in-the-dark paint for a spooky nighttime vibe.

It features Jack Skellington’s classic face, painted in black on a white pumpkin base.

Applying several coats of glow paint helps create a bright, even surface for the design. When lit in the dark, this pumpkin glows like a true Pumpkin King’s lantern.

Jack Skellington Table Pumpkins

A festive autumn table setting with carved jack-o'-lantern pumpkins, candles, flowers, and place settings, creating a warm and inviting Halloween atmosphere.

Bring a playful Halloween vibe to your table with Jack Skellington pumpkins surrounded by lush florals and glowing candles. The carved smiles pair perfectly with the orange and cream arrangements, creating a look that’s festive yet whimsical. It’s a centerpiece idea that feels both spooky and family-friendly.

White Jack Pumpkins

A long dining table is decorated with white and orange pumpkins, some with painted faces, candles, and flower arrangements in a bright, sunlit room.

These painted pumpkins capture the essence of Jack and Sally in bold orange and soft white, with those signature stitched grins. Nestled among flowers, mini pumpkins, and warm candlelight, they instantly set the stage for a cozy night-in or a kid-friendly Halloween gathering.

White and Orange Jack Pumpkin with Autumn Florals

A fall-themed table setting with plates, candles, flowers, and carved pumpkins featuring smiling Jack Skellington faces as the centerpiece.

Sometimes one Jack Skellington pumpkin is all you need to make a statement. Surrounded by colorful fall flowers and flickering candles, this design balances spooky with seasonal charm. It’s a wonderful way to add a touch of personality to a Halloween table without going over the top.

Jack Painted with Glow Paint Accents

A Halloween-themed table setting with carved jack-o’-lanterns, lit candles, autumn flowers, and dinnerware arranged for a festive celebration.

Jack’s face shines brightly with glow paint, making him pop in the dark. The glow highlights his iconic stitched smile and hollow eyes perfectly.

Using black vinyl or paint for details keeps the look sharp and spooky. A white pumpkin base with glow paint creates a magical Halloween vibe.

Sally Pumpkin Featuring Her Stitched Mouth

A carved jack-o'-lantern with a stitched mouth sits on a decorated table with flowers, candles, and plates, creating a festive Halloween centerpiece.

This pumpkin shows Sally’s soft smile with her signature stitched mouth in delicate black lines.

The stitches give the pumpkin a handmade, whimsical feel that really captures Sally’s charm.

Soft pastel colors and red hair accents bring Sally’s gentle spirit to life on the pumpkin.

Pastel Jack Skellington Pumpkins

Elegant table setting with pastel jack-o’-lanterns, pink and white roses, candles, and glassware arranged for a festive event.

For a softer twist on Halloween, these pastel Jack Skellington pumpkins are paired with blush roses, eucalyptus, and pink candles. The look is dreamy and elegant, making it a fantastic option for moms who love a little Halloween magic without the fright factor.

Sally-Inspired Patchwork Pumpkin

A decorated dining table with lit candles, floral arrangements, and pumpkins, including one painted in geometric patterns and another with a simple jack-o'-lantern face.

This painted pumpkin design channels Sally’s iconic patchwork dress with bright, geometric patterns. Paired with Jack’s mischievous grin on a smaller pumpkin, it brings the duo to life in such a creative way. Surrounded by flowers and candles, it’s a festive project that feels fun and artistic.

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