19 Smiling Pumpkin Designs to Make for the Happiest Halloween Ever

Pumpkins with Hair and Hats
Photo: Laura Moss

Browse our gallery of grinning happy pumpkin faces and gather some free downloadable pumpkin patterns for Halloween. With easy pumpkin carving ideas and free pumpkin carving patterns, you can find the pick of the patch for your family. Make a happy, smiling jack-o'-lantern face or make your kids smile with a funny pumpkin.

01 of 19

Pug Pumpkin

pug sitting next to pug pumpkin
Laura Moss

We love this adorable pugkin! You'll need one large pumpkin for the head, two small white pumpkins painted with black pupils for eyes, and two gourds for the ears. To attach the eyes and ears, make holes in the large pumpkin, white pumpkins, and gourds with a hammer and nail. Use pieces of a wire hanger to secure them. Paint a leftover piece of pumpkin red for the tongue.

Editor's Tip: Keep your jack-o'-lantern fresh with our must-have tips for making your pumpkins last longer.

02 of 19

Pumpkin Display

Pumpkins on stairs with painted faces
Adam Albright

Misshapen noses and oddball eyes may not win any beauty contests but these Cubist characters are sure to get the prize for creativity. Spray-paint clean, dry pumpkins in seasonal colors. Add details with a paintbrush and acrylic paint. Display the painted pumpkins with other assorted pumpkin varieties.

Editor's Tip: For crisp, clean edges, outline noses using a marker and flexible ruler.

03 of 19

Mustache Pumpkin

pumpkin with mustache
Laura Moss 

We mustache you a question: How cute is this dapper fellow?! Make him by cutting out a mustache shape from thick cardboard. Use hot glue to attach black licorice as the hair, cutting down the pieces as needed. Attach it to the pumpkin with pins.

04 of 19

Goofy Smiling Pumpkins

Goofy Smiling Pumpkins
Greg Scheidemann

These happy jack-o'-lantern faces elicit smiles—not shrieks—with zany bouncy-ball eyes and goofy grins (painted on using our patterns). They're easy to make and fun to display.

05 of 19

Grinning Pumpkins

5 pumpkins with different emotions
Laura Moss

These creepy smiling pumpkins are great for people on a budget–rather than splurge on huge pumpkins, buy several small sugar pumpkins for your kids to paint. To keep the carving to a minimum, cut just the mouths and paint on the eyes and other features. For extra depth, paint the inside of the mouths dark brown.

06 of 19

Vegetable-Adorned Pumpkin Duo

Two carved pumpkins with flowers
Blaine Moats

Floral shops and supermarket aisles are full of colorful, whimsical facial and hair ideas for your jack-o'-lantern friends. Here, we used cucumber slices for eyes, carved potatoes for ears, and ferns for feathery strands of hair. Creating this happy pumpkin couple is easy: Cut off the tops of pumpkins or drill holes to tuck in flowers and branches. Attach other accents with pins, toothpicks, or hot-glue.

Editor's Tip: Use battery-operated tea lights ($10 for four, Pottery Barn) to avoid the risk of fire.

07 of 19

Happy Halloween Jack-o'-Lanterns

carved pumpkins with party hats
Greg Scheidemann

Celebrate Halloween with this gang of happy jack-o'-lantern faces. Use the free pumpkin carving patterns to carve smiling eyes and wide grins. Then shape scrapbooking paper into cones, creating a variety of tall and short hats. Use tape to secure the paper in its cone shape. Cut out an assortment of circles from patterned paper and glue them to the hats for added flair. Trim some of the hat edges with a paper fringe. Hot-glue the hats to the tops of the pumpkins.

08 of 19

Veggie Pumpkins

2 pumpkins decorated with veggies
Ronald Andren

It's time to let your kids play with their veggies! Cut a hole in the top of your pumpkin, then use hot-glue to add leafy greens for funky hair. Halved peppers make great noses and mouths, green beans work as eyebrows, and cucumber slices stuck in apple corer-cut holes make great eyes.

09 of 19

Monster Pumpkins

monster pumpkins
Greg Scheidemann

Goofy grins and silly eyes hardly fit the scary jack-o'-lantern archetype. So if you'd rather laugh than be scared, these friendly funny monster pumpkins are the perfect addition to your Halloween decor.

10 of 19

Animal Pumpkins

mouse, cat, and elephant pumpkins
Laura Moss

These cute no-carve pumpkins are the perfect Halloween craft project for kids! Cut ears, eyes, and whiskers in different colors of thick construction paper ($5, Target). Turn kids loose with supplies, and they're sure to create a variety of animal-inspired ideas.

11 of 19

Goofy Group of Pumpkins

Group of carved pumpkins on hay
Greg Scheidemann

These funny pumpkins pack plenty of personality by playing up their flaws, so don't disregard that unusually shaped or scarred pumpkin. Arrange the carving pattern in a way that enhances a pumpkin's imperfections.

12 of 19

Dog Pumpkin Stencil

Pomeranian dog with carved pumpkin
Jason Donnelly

Carve a happy Halloween pumpkin inspired by your pet! Download one of our free dog pumpkin carving patterns and you're on your way to having a festive pumpkin in honor of your favorite pooch.

13 of 19

Hedgehog Pumpkins

candy corn hedgehog pumpkins
Carson Downing

Not all Halloween candy is for snacking! These adorable no-carve hedgehog pumpkins are decorated with cut felt pieces and plenty of chocolate candy corn. Use a hot-glue gun to attach the pieces to an artificial pumpkin and you'll have a long-lasting decoration.

14 of 19

Smiling Pumpkin

1 white 1 orange faced pumpkins on Adirondack chair
Peter Krumhardt

Create a goofy grin on your pumpkin by using an apple corer to punch perfectly round circles. For more easy pumpkin carving ideas, try using the punched plugs for additional features; here, the white-nose is a plug from a white pumpkin. Scrape just the skin away from around the punched "pupils" to create the eyes.

15 of 19

Funny Frankenstein

Fall décor with carved Frankenstein pumpkin
Carson Downing

There's no denying this Frankenstein pumpkin stencil's smiling face! This easy pumpkin carving idea is made from basic shapes—so it's perfect for beginners. Display your finished decoration with small pumpkins, green gourds, and colorful fall leaves.

16 of 19

Goofy Green Gourd

green pumpkin with painted face
Laura Moss

Don't be afraid to select uniquely shaped, bumpy, or colorful pumpkins—they have tons of personality! Use acrylic paints to doodle the smiling pumpkin of your dreams.

17 of 19

Stack 'Em!

3 stacked pumpkins with carved faces
Ronald Andren

Make a stack of jack-o'-lanterns easily with this shortcut: Use an apple corer to get perfectly round eyes in a pinch! Lightly scrape some lines for eyebrows above the holes for a quirky effect.

18 of 19

Glowing Guy

carved pumpkin with lights near tree
Laura Moss

To give your happy pumpkin a spiky light-up hairdo, drill holes in the top of your pumpkin. (Choose a bit that's slightly smaller than the light bulbs.) Push white holiday lights through the holes and place the rest of the light strand inside the pumpkin.

19 of 19

Hairy Pumpkins

Pumpkins with Hair and Hats
Laura Moss

These funny pumpkins are sure to delight your Halloween visitors! Start by selecting three flatter pumpkins and remove the stems. Use an old cap for one of them, braid thick lengths of yarn secured with ribbon for another, and cut out faux craft fur into "hair" for the third.

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