This is really the same cookie cutter twice, one modified by squeezing it horisontally and the other by squeezing it vertically. I've divided into five sections as I always seem to find odd numbers more asthetically pleasing. To add some additional texture, I've sprinkled alternate sections of the pumpkin with table sugar, allowed them to dry for 2 hours, then brushed the cookie with a silicone pastry brush and laid down two additinal pumpkin segments.
I left the top 1/5 of the pumpkin clear, then added some brown for the stem from an icing bottle. After about 30 minutes of drying, I switched to a forest green base icing with a #1 tip and created 3-4 tendril spirals at random locations.
After another 30 minutes to dry, I switched to a #67 leaf tip and created 3-4 leaves for each pumpkin. These can be done without the granular sugar accents, and I've experimented with heirloom colors (on which I think the sugar looks better). Were I doing a cinderella theme, something like this in a white with sugar accents would definitely be in my wheelhouse.