Select a variety of pumpkin shapes, sizes, and colors. For added personality, select ones with unique stems.
Before carving, group pumpkins in desired location and map out each one’s design.
Trace real leaves onto paper, or use patterns from botanical "clip art" books. Experiment with different leaf size and arrangement.
With a saber saw or pumpkin-carving tool, cut out the top of each pumpkin. Scoop out seeds and strings with a sturdy metal spoon. Then use a pottery tool called a loup, a small metal ladle, or a melon balers to scrape out as much of the interior as possible, especially where you plan to carve (this will make carving easier and allow for better illumination).
Before copying a design onto a pumpkin, clean the entire surface with a damp towel, then wipe with another towel until exterior is completely dry. Secure paper to pumpkin with masking tape or pushpins. Use a pushpin, embroidery needle, or metal skewer to prick your design onto the pumpkin.
Cut along transferred design lines using a saber saw, pumpkin-carving tool, small paring knife, or linoleum-cutting tool (similar to a box cutter). Shorter bladed allow more control.
To keep your designs looking fresh, apply a thin layer of petroleum jelly or vegetable oil to the pumpkin's carved cervices.
To get the right amount of glow in a pumpkin lit by candles, use multiple tea lights.