The type of tomatoes you grow can make a difference in when and how you should harvest them. Let’s talk about three of the most popular types to give you an idea of how tomatoes vary in their growing and harvest seasons. Cherry tomatoes should not be harvested at one time. Since this type of tomato grows on a truss, the ripening tomatoes can weigh down the truss and take nutrients from developing fruits. Instead of waiting for all the tomatoes on the truss to reach the red stage, I recommend that you look for and pick individual tomatoes when they reach the stage you think is ideal. This applies to current and grape tomatoes as well. Heirloom tomatoes should be picked before they reach the red stage. I think they get too heavy for their vines, and they are too attractive to pests to leave outside.Again, you can grow them any way you want, but I have found that they do best when they are picked at the pink stage. Roma tomatoes are another tomato type that I prefer picking at the pink stage. Some gardeners like to leave them a little longer, so they develop more of that red skin that is excellent for pasta sauce, but this is not necessary.  Again, it is up to you.