dkotchey,
I had wonderful success wintersowing tomatoes. I have just done 4 varieties last week and still have 2 more to go. Peppers have been another story. I don't have luck either wintersowing or buying pepper plants. They just don't do much for me up here.

Penny

I will agree with Penny.

Tomatoes may, at first, look behind, but, in fact, they will catch up and be really healthy and yield more than you would expect--as long as we have a somewhat regular summer. I winter sowed romas, big beef and a heirloom variety last year. This year, I will also try first lady--an early variety.

As for pepper plants, I only tried them last year indoors, under lights. However, the year before, I had volunteers (probably from my compost pile) in my perennial bed --with very little space around them to grow, and.. surprise, they did give me a few peppers by the end of August. So I would not rule them out. Since I only need 2 or 3 plants, I will continue to start them indoors this year again, but I think you should give it a try. Without a warm summer, don't expect a big yield, whether you started them indoors or winter sowed them....
Good luck,
Anne-Marie

Starting the tomatoes and peppers inside last year, we did quite well with peppers (mostly hot peppers, but a few anchos) and decently with tomatoes. If you want to write off tomatoes every so often, winter sow them. If you want tomatoes every year no matter what the weather, start them under lights and grow relatively early varieties.

I'm going to give tomatoes a try. This is my first year winter sowing and I'm more of a veggie planter than a flower planter so I'm trying tomatoes, lettuce, cabbage, and cauliflower. I'm not sure how to plant or harvest broccoli or I'd give that a try too. Anyone else doing other veggies?

I'm doing veggies this year also (it's my first year for WSing anything).
So far I've done three types of tomatoes, (Roma, Early Girl, Early Bird HB), kale, Red and Green Oakleaf Lettuce, Zucchini Squash, Mesclun Mix, and Mustard Spinach. I may have done some more, but I'm kinda falling behind on keeping track lately. I have to catch up my database this week before I start my hardcore sowing of annuals.

Tomatoes are do-able but choose early varieties.

Peppers on the other hand don't seem to offer varieties as early as tomatoes, therefor the experience appears to indicate that WS is less adaptable for that fruit. That said, they will produce, you just wait a bit longer.

This year in the tomato category I have WSed Super Marmande, Black Krim, Bloody Butcher and Roma; my pepper choice is always Cubanelle which I WSed a week ago.

I have to say that last year was my first at wintersowing tomatoes and they were very hardy and plentiful. I am doing it again this year. I didn't pay as close attention to my peppers though and they dried out. Good luck.