I've got delicata squash growing on both sides of the garden (from one plant located somewhere near the center of that mess). I've been watching the largest and wondering how to tell when it's ripe. One online source suggested to leave them on the plant until the plant dies, or until frost is eminent. Another suggested it was ripe when the vine starts to die away where the fruit meets the vine. Another said simply to compare it to the photo on the package. Well, it looks like the package, and the flesh is starting to turn yellow, but the plant is still quite vigorous. But today, I went to look at the bottom side to make sure it wasn't rotting, and the whole squash came right off in my hand! I guess it's ripe enough to pick now. The bottom is still white - no green stripes, but the flesh resists a thumb-nail as most squash webpages suggest. I'm going to set it aside for a while to see if that white spot colors up. I'm told delicata squash doesn't need to cure, but it won't hurt it either. And if I mess it up, there are at least a few more still on the vine.
The winter sown tomatoes are looking wonderful! In fact, out of all of the plants, only two of them have not started flowering yet. Most have fruit growing, and some of them are starting to get stripes (though they're all still green at this point). The Solanum Spontaneum I planted out at my Mom's house is small, but doing alright. Last time we visited a few days ago it had one that looked almost ready to pick. I'm hoping it hasn't gone too long on the vine by the time we head back out there tomorrow. I'm definitely going to winter sow again this year, especially my tomatoes and my squashes!