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Step-by-step build — 3 steps. Also available as a print sheet.
Glue and nail (or staple) the fence picket pieces together with about a 1" overlap between each board — this overlap is what gives the finished shape enough thickness to stand on its own. For the larger pumpkin, add two additional layered pickets.
Freehand a pumpkin outline with a pencil — every pumpkin is a little different, so any reasonable shape works. Cut with a jigsaw and lightly sand any rough edges.
If you want a two-tone look, paint or stain the pumpkin now, before the stem support goes on, and finish the stem separately in a contrasting color if desired.
Glue and attach the stem support and backer piece to the back of the pumpkin. Nail or staple from the fence-picket side into the back of the support piece, positioning it so the pumpkin stays upright and stable.