Dig a hole 2 feet wide and 1 foot deep. Add compost to create a mound.
Plant five seeds per mound, 1 to 2 inches deep. Once they start to grow, thin to two plants per mound.
Water deeply and infrequently and keep the weeds out. Side dress with a 34-0-0 fertilizer after the vines develop runners, recommends the Utah State University Extension. Avoid using insecticides, as this can kill the bees necessary to pollinate squash and pumpkins, notes the University of Illinois Extension.
Harvest once the winter squash turns a deep, solid color and attains a hard rind. Cut the squash from the vine carefully, leaving 2 inches of stem still attached.