I would like to suggest, rather than trying to create something perfectly on the computer (which could take hours!) to help you cut the pumpkin make a hybrid template (a combination of computer generated text/images and hand drawn elements).
Your scrapbooking cutting skills (scissor, die cut, cricut) & alphabet knowledge (for titles) are probably a lot better then your "generated something graphically from scratch on a computer" skills.
In fact...this may be the perfect opportunity to use up some old alphabet stickers. Either by placing them directly on the pumpkin, use them as a stencil on the pumpkin or by using them to create a template for the pumpkin.
I would go for, applying the alpha stickers on the pumpkin until you get them the way you want, get out a knife, and cut them out of the pumpkin. Then draw a vine, leaves, and the rings. Then decide if you want to cut them out too.
and, I can't said it enough times because I have made the same mistake, it's better to just "wing it" using old school skills like drawing & cutting then to spend HOURS making sometime perfect on a computer just so you can cut it out. Use your computer for the text if you have too but don't go nuts trying to make the whole image just perfect. It's a lot faster to have a couple failed scissor attempts.
PS and don't forget to leave little bridges in place to hold sections of the pumpkin in place. Example: you are cutting the ring. leave several little bridges to hold the center of the ring otherwise you end up with a giant hole.