Mid-may is good for tomatoes, after danger of frost so you don't have to protect them. Squash/pumpkins do well if you start them in peat pots a few weeks ahead of time, I do so routinely then set out towards the end of May. If you have a striped beetle problem, and you aren't growing organic, you can water them with an imidacloprid solution before setting them out, it's labeled for vine crops and gives close to season long protection that way.

I think you'll be ok to plant in mid-June, just get them in as soon as you can. I rarely put out the tomatoes until after Mother's Day anyway. I still think you'll beat an early freeze, and if not, pick green and store. I've never had much produce come from a pot, compared to planted in the garden.

The pumpkins are the only thing I'm not sure you'll have time.

Thanks for your help! I will try to keep my from seed tomato plants healthy enough for mid-June and pray that it ends up being early June instead!

I probably start the squash & pumpkin in-doors too. And then set out. bbriggs - I don't know if I'll have a striped beetle problem, this is our first year gardening here. I've talked to my neighbors and none of them have had veggie gardens. In CA, I expected that but here in IA - I guess I just thought people were a little closer to the soil here. LOL! So much getting a low-down on the bug problems!

If you keep your tomatoes until mid June, and they get quite tall, dig a trench about 5 inches deep and lay the tomato plant in it and then very carefully, tip the last 5 or 6 inches up and cover the remainder of the plant. Take all the leaves off, below the surface. I do this every year, with very good results. Stan