Ok, this guide is based on my experiences as an assistant manager for the produce department of a Detroit area kosher grocery store. Your mileage may vary.
To get the freshest produce, you want to get it as soon as possible from the source. Most likely, you buy your fruits and vegetables from a grocery store. They (most likely) get them from a large distribution center, where trucks bring the stuff from all across the country. In Detroit, that place is called the Detroit Produce Terminal, and it handles basically all the produce sold in Michigan.
Some things to do to get the freshest possible produce:
-Never buy anything from the top of a bin or the front of a display
Whoever owns the store wants to sell you old crap. This is a given. In the store where I worked, the motto was, “someone will buy it”. When displays are restocked, everything is removed, the fresh stuff is added, and then the old stuff is put back on top. This prevents the product from sitting too long at the bottom of the barrel and rotting. To get to the good stuff, just dig around a little. This is especially important for things like cherries, where a day or two makes a big difference.
-Never buy anything that has been packaged
When stuff gets too crappy to sell normally, the number one thing to do is package it. Often, these packaged things will be marked discounted and sold for a fraction of their original price. However, sometimes this stuff just gets put back on the shelf. The package makes it that much harder to inspect the product. It is especially bad to buy cored pineapple and sliced fruits, the exception being watermelon.
-Find out when your store brings in fresh produce
Most stores will get stuff twice a week, regardless of size. You can find out which days by befriending a worker, trust me, they’ll be happy to have someone to talk to. Once you know which days the fresh stuff comes in, come late in the day. Most places spend all morning loading and unloading, and then bring the stuff out to the “showroom” in the afternoon.
-Don’t assume there’s fresher stuff in the back
Most of time, the produce in the back is just as old as the produce that’s out. The only real exception is on days when they truck stuff in. On those days, it is advisable to ask for fresher from the back.
-Don’t think for a second that you can get anything “farm fresh”
Many people think that the best way to get fresh produce is from a roadside stand out in the country. That’s simply not true anymore. Those roadside stands are cash cows for whoever owns them. Most of the time, they truck in at least half of the stuff they sell. Yes, sometimes what they do sell is very fresh. Oftentimes though, all they’ve got is exactly what you’re grocery store has.
-Don’t buy anything late in the season.
Late in the season for a particular product, it is very likely that what you are getting is the remnants left over from a warehouse somewhere. Sometimes the fruit has to come very far. This accounts for the price as well as the poor quality.
-Check your boxes
Many times, the displays which hold the fruit in the showroom are made of the boxes the fruit came from. Check the boxes to see where it was produced. The closer to your area, the fresher the product should be.
-Ask your produce department friend to tip you off when “special deliveries” arrive
Sometimes the store will get a special offer, like someone representing some farmers will sell them a few boxes of pickles. This produce is usually especially fresh.
-If you need the absolute freshest fruit, consider a trip to your own distribution center
It is possible and fairly easy to set up an account and purchase boxes of fruit on your own from someone at your local produce terminal. Poke around to find out where it is, and then take a trip. You’ll need to go early; everything starts arriving around 1 in the morning, and is gone by probably 2 p.m. You’ll have to be willing to buy boxes of probably 20 lbs minimum for most types, but with things like raspberries and strawberries the minimum should be much less. Plus, you’ll get your produce super cheap. Most of the time, the profit on each produce department item is something like 100%. At my store, the produce department single handedly kept the store afloat. No other department in the entire store made any money, ever.