I am kind of a newbie with pumpkins and squash...but it sounds like you are doing fine. Raised beds and in-ground certainly needs less ferts than containers....especially if you enhanced prior to plant out. Be careful about spraying during hot sunny weather. I think these squash leaves are fairly tender because of their size. My full sized pumpkins have lots of issues in my 10 gallon pot. I am going to find more ground space next year for the squash and pumpkins. I think they are rough to grow in containers....depending on variety.

Nobody can say how long your "organic fertilizer" will last, particularly having no idea what it might be. I think your best bet is to keep an eye on the vines and if they're growing and healthy-looking then they have enough.

I also don't know how large your squash bed is, or what surrounds it. Four feet apart is pretty congested and I guarantee their roots are competing with each other. Furthermore, the roots want to extend basically far as the vines, but I doubt they will be able to. That's often the problem growing huge roaming winter squash in small beds. When I've done this the fruit quality suffers badly.

Depending on what sort of winter squash you have, it might be putting down roots at the leaf joints. The Maxima species of squash will do this but I don't know what sort of squash you're growing.

This year I'm growing three Butternut squashes in a 22'x24' cultivated plot. That may seem quite large but I feel it is too small as the vines have already crossed each border at warp speed. My concern is mostly that the roots have enough room to spread. I use compost and soybean meal before planting and work in more soybean meal twice during the growing season, just out beyond the growing vine tips. I just did this recently and that's all they'll get for the year.

Wow, thanks for the info everyone. I guess I planted a bit too densely this year, reason being that it is in my front yard in an urban area... Granted it's a big front yard, but still no place for vines to root unless I want to tear out turf. I do make sure to give the bed a good soaking every four days or so, and fed the bed recently with typical slow release blend organic fertilizer (fish etc. and minerals in powder) so it should hopefully have nutrients for end end of the season.

I think all three species in the bed are c. Maxima... One is a full-sized Hubbard type. It will be fun to see how they turn out.

I imagine the fruit will be small, but I am hoping if I can keep the mildew back and rodents at bay, at least the fruit will mature. Last year I planted in a worse spot, only got three undersized fruit, but they matured, stored for months and had good eating qualities so this year is probably an improvement.