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The most important step before you begin to make homemade whipped cream, is to make sure everything is really cold. Place the beater and the bowl of the mixer in the freezer for about 15 minutes. Also place the heavy whipping cream in the freezer at the same time.
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As the beaters whip the cream the coldness of the bowl helps the cream maintain its structure. If the cream is not cold, it will have a little more liquid at the bottom.
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Place the cream, powdered sugar and vanilla in a stand mixer. Turn the mixer on low at first, until all the ingredients are fully mixed. Then turn the mixer on medium speed. Medium speed is key to making the best homemade whipped cream.
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Whip the cream until almost stiff peaks form. The best way to tell if it is ready, is when the beaters are lifted out of the cream you can see little peaks that do no fall right away. If you mix too much you will make butter. The best whipped cream is right before it gets to the butter stage.