Yes, it is possible. They are actually the same plant (Cucurbita pepo) - just different forms.

Woah! Very cool!! :-) I thought one was summer squash and another was winter.

Well, they are different cultivars and have different uses but botanically they are the exact same species. Squash are very promiscuous so chances are if you had pollinators around they would have already done the cross pollinating for you.

Rodney

If you feel like letting that zucchini grow to full size and saving the seed, what grows next year out of those seeds will likely be a cross between the two squash types. It is not a recommended practice though, because it frequently results in squash that taste bad and have unpredictable growing habits. Plus it wastes the zucchini you pollinated. Many experienced gardeners have grown at least a few volunteer mystery squash from time to time.

I haven't seen a single bee this year, not sure where they are, so I have been hand pollinating this year. End of the season last year we had army worms but we sprayed with organic pesticides that might have killed the bees, hope not. I didn't see any bees when I was spraying. Hope the bees do come back. I saw one SVB that I killed, and ladybugs, and a few cucumber beetles, but no bees yet. I'll be sure to eat this zucchini, won't save seeds.

Try planting a few bright colored flowers near the zucchini. They will help attract the bees.