Based on your post, I assume you are talking about a vegetable garden. With winter sowing you won't do all plants at the same time. This is true for either flower or vegetable gardens. I assume you may already know that.
There are a ton of sites to look at to give rough timelines. Do a search for "winter sowing zone 5" and have fun reading. If you have specific things you want to plant I can give some suggestions.
We gave up on the veggy gardens a few years ago as it required extensive fencing to keep the rabbits, groundhogs, turkey, deer, and every other animal that came in and had all-you-could-eat breakfast, lunch, and dinner. Even the fencing didn't stop 'em. The only thing we didn't give them was the croutons for the salad
