Known for their delicious meat and decorative skin, Winter Squash is a must for your garden this year. Plant winter squash in a sunny spot in fertile well drained soil. Transplant winter squash, once risk of frost has passed. Winter Squash takes a long time to reach maturity, but once ready these hard skinned squash can be stored all winter long. Give Squash consistent water and plenty of space, and they will take off. Squash is ready to harvest when the stems brown and the rind turn hard enough that it cannot be easily punctured with your fingernail.