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Timing is everything when it comes to produce
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Fruit and vegetable prices will change throughout the year due to seasonality and location. By buying fruit that's "in season" in your area, you'll save money and get the freshest produce.
Just because something is available at your grocery store doesn't mean that it is fresh or that it is a good price. Be aware that most fruits are flash frozen so that they can be made available all year round. While this is convenient, you pay for it since out of season produce carries a heftier price. Produce that's in season, however, will be less expensive and taste the freshest. Search Sustainable Table to see what's fresh in your area and let the produce determine what's on the menu tonight!
If you don't have the time (or desire) to learn about what's in season, just get in the habit of picking up whatever's on sale. This will change from week to week which means you'll get great variety while keeping your budget in control. While it's fairly easy to figure out what's on sale, it can get confusing for some items -- especially berries -- which get packed in many different container sizes. For example, $2.99 might seem cheap for blueberries, but if it's only a 4 ounce container that's like paying $12 per pound.
Ideally you would keep track during the year of prices and sizes for your favorite produce so you can easily recognize a great deal. Alternatively, try to compare prices across stores using weekly circulars. If you don't have any of those available, look for a discount that is 50-75% off the regular store price which is usually a sign of a very good deal on in-season produce.
The other key question is how much to stock up on produce when it is on a great sale. Early in the season you can get away with buying less per trip, since you can expect to find deals running for several more weeks. However as you get near the end of a fruit's "in-season" you will want to stock up a bit more. You can plan to freeze or jar some produce which let's you "extend" a great deal for many more weeks and months. Otherwise plan to buy enough so that you can eat most it before it rots. But keep in mind that even if 1/4 of the discounted items go bad before you can eat them, you're probably still coming out ahead versus paying full price and eating the whole batch. So stock up a little extra when it's a great deal!