Web app Food on the Table creates weekly meal plans and grocery lists based on food you (and your family) enjoy, then hooks into your local grocery stores to find the best deals on your groceries. It's kind of brilliant.
After you sign up for the site, you'll walk through a little setup in which you identify your main grocery store and check off the foods your family likes to eat (namely meats-it'd be nice to have more fruit and vegetable choices). Later, you can pick another nearby store if you want to compare prices.
Next you're presented with a list of items (based on your preferences) and asked: "What are you in the mood for this week?" Make your choices, select the number of meals you're ready to plan and choose what you care about most now: saving time, money, health or variety. At this point, the site searches through recipes that match your needs, prices out the cost of the meal for you, and lets you print out your shopping list.
It's hard to tell if something like this would work for you in the long term, but in theory, at least, Food on the Table is a really smart, useful idea. If you want more features than the basics mentioned above, you can upgrade to their premium account; the free version seems pretty serviceable as is, though. If you've used it — or something similar — in the past, let's hear how it worked out for you in the comments.