Reddit reviews Extreme Pumpkin Carving, Second Edition Revised and Expanded: 20 Amazing Designs from Frightful to Fabulous (Fox Chapel Publishing) How to Use Relief-Carving Techniques to Create Realistic Features
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Used Book in Good Condition
Just use normal woodcarving tools. Get a cheap set since you'll be carving soft pumpkin flesh. Buy this book:
Extreme Pumpkin Carving, Second Edition Revised and Expanded:How to Use Relief-Carving Techniques to Create Realistic Features
Used copies are pretty cheap.
And just practice. Ignore the comment about using clay, it's an ENTIRELY different medium, and if your goal is to just do this with pumpkins, work with pumpkins. Though for the record, a little experience with sculpting faces, especially relief sculpting, in any medium will help. Not required though. That book is pretty comprehensive though.
For reference, here's the pumpkin I made last year, using my co-workers face as inspiration. And I've only ever had that book as a way of reaching this sort of thing.