Have a serving platter ready to assemble the icebox cake.
Beat the whipping cream, vanilla, and icing sugar in a stand mixer (or with a hand mixer) until stiff peaks form. Reserve half the whipping cream in another bowl and set aside.
Set aside half of the raspberries for garnish. Take the remaining raspberries and mash them with a fork until a jammy consistency is reached.
Gently fold the mashed raspberries into one of the two bowls of whipping cream until well combined.
Carefully spoon about 2 teaspoons of raspberry cream on top of a chocolate wafer.
Top the cream with another wafer to make a sandwich cookie. Continue to layer the cream and cookies until the stack is 9 cookies tall. Repeat this step until you have 4 stacks of 9 cookies.
Lay each cookie stack down, side-by-side on your serving platter so the rounds of the cookies look like the wheels of a train. The stacks should fit snugly together! If you have any raspberry cream left, use it to adhere the stacks together.
Take the reserved whipped cream and spread it over the cookies much like icing a cake. Try to cover up any imperfections, but note it may look a little messy. It will work out we promise!
Place the cake in the fridge to soften the cookies for at least 4 hours.
Just before serving, decorate the cake with the remaining raspberries. Add fresh mint leaves and edible flowers if you like.
To serve - slice the icebox cake like a loaf of bread and serve individual slices.
Notes
Make this recipe dairy-free with dairy-free cookie wafers and coconut whipped cream.Substitute the chocolate wafers for vanilla wafers, ginger cookies, graham crackers, or any other thin wafer-like cookie you like.Vanilla extract can be substituted for almond extract, peppermint extract, or any other flavouring you prefer.You can substitute white sugar or organic cane sugar in the whipped cream.Use any other fresh soft berry you have on hand or is in season. Blackberries are also great!