I think our growing season is too short to winter sow most tomatoes. I missed a Beam's yellow cherry tomato during garden clean up that self sowed last year. It didn't come anywhere near flowering, much less fruiting by the end of the season. If you're going to try, pick ones with the lowest number of days to production (check the seed packet) maybe Stupice (50 days) or Bloody Butcher (55 days).

Thanks. I think I'll stick with flowers!

I tried winter (well, 3/10) sowing for the first time this year, but didn't do tomatoes; I usually start them indoors.

Broccoli and marigolds are about an inch tall and seem to be doing really well outside, though; garlic is a few inches tall, and the onions seem pretty happy too. The other items haven't come up yet.

I definitely second Barb. Winter sowing warm season crops is most likely to end up frustrating you. I winter sow lots of native perennials because it's the easiest way to stratify them I think. That is until they germinate during a week of 60's in February and get hammered by single digits a month later....

You pretty much missed the window for winter sowing this season, I'd try again next year. For success you'll want to get them in containers early to mid January. Hardy perennials seem to do best, have had no success with vegetables.

I do not have great luck with winter sowing, of course with the exception of garlic which does amazingly well no matter what. I think the soil in my containers just gets too cold, even with small greenhouse cloches over them. Even starting lettuces and other cool season veggies from seed too early in February doesn't produce great results. We have a plenty long enough season to start them later (in April) and have much better results by letting the soil warm some before sowing the seeds. We also generally have a very nice autumn season, so starting the same cool season crops in mid-late August usually produces a very nice extended fall crop.

I have had good luck direct-sowing micro tomato seeds in June and having ripe fruit by August. The only tomato plant I've found that can do so in such a short amount of time.

I tried winter sowing for vegetables and herbs and failed abjectly. I had some decent germination but very few successful transplants out of it. Some of it was user error, surely. But I'm not bothering with it again probably.

I didn't do any winter sowing where you put a milk jug over it to protect the seeds; however I direct sowed lots of flower seeds this winter (poppies, lupine, larkspur, blue flax, cosmos, baby blue eyes, desert bluebells, rose campion, gayfeather, and a couple others that I can't remember right now). Pretty much anything that says that it self-seeds, I figured should be able to stand or even appreciate the weather. I have no idea if they will come up or not; it is a grand experiment. I worry slightly that some of them I may have planted too late; I didn't realize that some establish roots in the fall and then go dormant to spring up in early spring.