I would space items that make big vines, like squash at least a couple of feet apart. I space zucchini hills about 3 feet because they are too hard to reach the fruit without stepping on vines. 2 plants per hill. After trying to harvest sprawled cucumbers once, I now always provide something for them to climb on. They are just to hard to harvest without stepping on plants and fruit, and it is too easy to miss a fruit, then it gets too ripe and the vines stop producing. In a pinch I will use those small tomato cages, but my favorite supports are teepee-style sticks with string or more sticks going across the support sticks every 6 or 8 inches. I can build these supports quickly and for free with any sticks pruned off my own trees or I have also foraged through neighbor's trimming piles. I get compliments on how they look once the cucumber vines get going. I space 3 or 4 support legs for the supports about a foot apart, pushing the sticks a few inches into the ground, then I tie the tops together. I plant one cucumber by each pole and one more in the middle. Sometimes I plant nasturtium between the cucumber plants, but only one per teepee so things don't get too crowded.
As for winter squash, I like to use them as living mulch in areas I don't want to weed or water much. You can use them 3 sisters style with sunflowers or corn. I planted them in an unused RV pad full of rocks that grows lots of weeds and a few blackberry and currant plants. I raked back the rocks to make a few 2 foot diameter circles and made piles of aged manure and compost, planted the squash and then mulched with grass clippings and wood chips. I watered daily until the plants were established and then only twice a week after that. The squash plants got huge and vines out several feet in all directions which helped with water retention and weed reduction.
I have used squash around trees before and ended up with Cinderella pumpkins hanging from tree branches, which made unusual but amusing decorations. The vines will climb whatever they can.
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