Winter squash takes up so much room in the garden. To rectify that I sent mine down the garden wall as my garden is in a planter that is raised from 3 to 6 feet off the ground. Another option is to let the squash climb a wall or lattice such as Martha Stewart shows here. Pick winter squash when the stem is dried out and leave the stem on the squash. Pick before frost. The taste will not be as good if frost hits the squash.