I live in Illinois, and there is currently nothing in season right now. In my ideal world, I would have preserved enough to be able to get through the winter, but I'm not there yet. So what am I doing?
From the Health Food store, I purchase apples, carrots, and lettuce. These foods have the highest pesticide load and so I purchase them organic. My health food store buys as local as possible, so I feel that is better than by organic at the Grocery Store. I also purchase local, organic milk, butter, cheese and eggs. I check the prices of the local meat, and occassionally purchase some. I would like to purchase more local, organic meat, but it is just too cost prohibitive.
Then I shop for the bulk of my other food items at Aldi's. As much as possible, I try and buy "whole" foods there and cook from scratch. (I do offer lunch and snacks for the daycare/preschool/homeschool children and do use some packaged food with them.)
Finally, I buy my "brand" grocery items at Kroger. I went through a period where I was watching the grocery flyers and if another grocery store had some of my "brand" items on sale, then I would get those at a different store, and others at Kroger, and sometimes some at Target, etc. It just got to be too much. I do use manufacturer coupons for these items when I have them, and Kroger sends me coupons for these items too. (There is probably only 15 brand items that are just HAVE TO items - Angel Soft toilet paper topping the list.) So it really just wasn't worth my time driving all around to get the best price.
I do eat the beans and tomato sauce that we canned at least once a week too.
Shopping like this, I can usually spend just over $350 a month for our family of five, plus lunch for 9 during the week. I generally buy from the Health Food store once a week, and Aldi and Kroger once a month.