I decided to make a shaped cake (without a mold) for a 5 year old friend's birthday. I had an idea and went with it, but until I was 90% I was sure I was going to have to rush to the store and start over by making a FLAT rectangular brithday cake, but it turned out surprisingly well.
Its the shape of a 5, but the circular part of the 5 continues to swirl up and around into a hill.
So here's the trick: Bake, cool (overnight is best), shape/cut the cake, then make a batch of thin frosting. Use this frosting to glue the cut pieces to eat other and then frost the cake. At this point it will look horrible b/c all of the crumbs will get caught up in the frosting. Don't stop. It will be okay! Let the cake dry for an hour or so. Make another batch of frosting the consistency you like (I made butter cream) and spread it on. The first layer of frosting will keep the crumbs and you'll end up with a nice smooth (non-crumby) finish. Decorate.
Since I had about 1/2 a cake left over, I crumbled the remaining cake up and turned it in to the road. I also made a pile of dirt (chocolate cake crumbs) in the corner, so I didn't have to be so careful about being tidy while applying the road. If I dropped some, I just swept it over to the corner with a pastry brush and added a dump truck when I was finished!
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