CricutPumpkinCarving

I think a craft cutter is one tool that every school and makerspace should have a couple of. They are a relatively inexpensive foray into digital design where measurements matter. You can cut paper, cardstock, food box cardboard and vinyl (stickers, window clings, iron ons).
I have a Cricut which came with their Design Space Software. If you have a Cameo, I assume you use Silhouette Studio, which has a basic free version, then paid upgrade versions.
The steps should be similar...maybe the tools have different names.

Silhouette Garden https://silhouettegarden.com/ and Flaticon https://www.flaticon.com/ are great sites to get free and copyright free icons to use for projects. Usually they just want attribution. Silhouette Garden gives you a zip file with svg, png, jpg, eps, and dxf formats ; Flaticon has png & svg formats.

1) Upload a pumpkin svg (or whatever shapes) to your software
2) Import it/them into your project
3) Find these tools Weld, Slice , Group.

Ring to Hang:
1) Make 2 circles, one smaller, put them on top of each other
2) Select both and click Slice
3) Grab the outer ring and move it onto the pumpkin
4) Select the ring and the pumpkin and click Weld
5) Delete the two smaller circles

Face Carving
1) Pick a shape for an eye, size it and put it into place
2) Select the eye and the pumpkin then click Slice
3) The pumpkin now has a hole in it and there are two "slices" the shape of the eye that you can delete.
Slice only works with TWO objects, so you have to do each feature one at a time.
Repeat those steps with the other features you want to cut out

Add Ons
If you want to add on to your pumpkin -- arms, wings, hats ...
Bring in another SVG
Attach it to the pumpkin
Select both
click Weld
Weld works with multiple items, so you can weld them all at once