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Cute Winnie the Pooh Cupcakes

With the new Christopher Robin movie, we have all seemed to fall in love again with the silly old bear. Winnie the Pooh is a classic Disney character that has made kids and adults happy for decades. Add in the fact that Winnie the Pooh was created in a real-life 100 Acre Woods and it’s easy to see why we all have a soft spot for Pooh Bear. So everyone will love these cute Winnie the Pooh Cupcakes!

cupcakes with yellow Winnie the pooh faces

It only takes a couple specialty baking ingredients (that you can easily find on Amazon – use the links below) to look like a rock star making these classic Winnie the Pooh cupcakes.

These kid-friendly treats are great for birthday parties, baby showers, bake sales, literary events, Halloween and celebrating the newest Winnie the Pooh movie.

Winnie the Pooh Cupcakes

Winnie the Pooh Cupcakes


  • 12 of your favorite chocolate cupcakes (we baked them in a red cupcake liner)
  • 8 oz. yellow fondant
  • Cornstarch for rolling
  • Cookie cutter, about 2 inches in diameter
  • Bowl of water and a paintbrush
  • 1 stick butter, softened
  • 2 cups icing sugar
  • 2 tbsp milk
  • 1 tsp vanilla extract
  • Black decorating icing

chocolate cupcakes in red wrappers with bowl of white frosting and yellow fondant

Yields: 12 decorated cupcakes


  • Allow your cupcakes to cool completely before decorating. Line a baking sheet with wax paper and dust your working surface with a thin layer of cornstarch. Roll your fondant to be about ¼ of an inch thick and use your cookie cutter to cut out 12 fondant circles.

yellow fondant circles

  • Next, roll spheres about one inch in diameter, you’ll need twelve of these. Flatten them out and shape them into ovals.
  • Roll 24 smaller spheres and shape them to look like Pooh’s ears (flat and pointed at one end).
  • Using a stand mixer, beat butter, icing sugar, milk and vanilla extract until smooth. Use an offset spatula to frost each of your cupcakes.

chocolate cupcake with red wrapper topped with white frosting on a baking rack

  • Assemble your fondant pieces: place your flat oval in the center of your large fondant circle. You can brush water on back of the oval so that it sticks onto the circle.
  • Using Wilton tip #7, draw Pooh’s nose and eyes with black frosting. Switch to Wilton tip #6 and draw on his eyebrows.

cupcakes with yellow Winnie the pooh faces

  • Place Pooh’s face on each cupcake and apply his ears (brush the back of each ear with water to secure it on his face).

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