While the cupcakes bake, work on the whipped cream frosting. Chill your mixing bowl and whisk attachment in the freezer for 30 minutes to help this whipped cream frosting whip up better.
Place 1/2 cup (4 oz.) of cold cream cheese into the chilled mixing bowl and mix on a medium speed until smooth.
Add in 1/2 cup of powdered sugar and mix on low at first to avoid powdered sugar clouds/explosions. Increase the speed to medium-high once the powdered sugar is incorporated and mix for about 1 minute. Scrape the bowl with a rubber spatula as needed throughout this process.
Add in 1 tsp of vanilla extract, then turn the mixer to a medium-high speed and gradually pour in 1 1/4 cups of cold heavy cream. I like to do this in 3 additions and focus on pouring the heavy cream down the side of the bowl to prevent it from splattering.
Watch the mixture closely once the heavy cream is fully mixed in. It should thicken and take shape shortly after this (mine usually does within about 30 seconds of mixing after I've added in all the heavy cream). Take care not to over-mix this whipped cream frosting!! It will become soupy and difficult to fix.
As soon as you see the frosting start to take shape, turn off your mixer and do a quick whisk test. Dunk your whisk attachment into the frosting, then take it out and flip it upside down. The frosting should keep its shape and form a nice peak. If it doesn't, continue to mix the frosting on a medium-high speed for 30-second intervals until it does.
Once it passes the whisk test, place the whipped cream in a large piping bag fitted with a Wilton 1M piping tip and place it in the fridge until you're ready to use it or until the cupcakes have fully cooled.
Pipe a large swirl on each cupcake, then top with fresh berries (I used blueberries, raspberries, blackberries, and halved strawberries) and a dusting of powdered sugar, and enjoy! I also love to top these with macerated strawberries by slicing up a pound of strawberries and mixing them in a bowl with about 3 Tbsp of granulated sugar, then letting them sit in the fridge for about 30 minutes.