I began setting out tomato plants in the first week of June. In this photo, you can see me posing with some of my largest plants just before I set them out. Also note the vast number of tomatoes in the greenhouse behind me. Many of those were set outside that day on the lawn. It then rained overnight and they were planted the following two days. Since these have been in the greenhouse (with the windows open) they did not need as much hardening-off from the elements as would the the indoor plants.
I first put the plants in my humble old wheelbarrow and bring them to the garden. It makes it easier to have them raised off the ground when trying to separate the flats because the hairy leaves love to cling to the other surrounding plants. Plus it's easier to move the remaining flats down the row as you work.
Here's a good photo of three essentials needed for an easy day of transplanting from the flats to the garden:1) The handy garden bench (I make these myself). This custom made, very sturdy bench is made to fit lengthwise between my raised bed rows. I sit on it facing the transplant hole then move down to the next spot.
2) The 2nd most important item is a mini garden spade/hoe. It's so much better than a mini shovel, try one for yourself! I purchased this one for $14.99 at my local farm & pet store and would gladly pay double if I had to - that's how good it works!
Note: It's perfect for mixing concrete too - I've thrown my back out mixing with a shovel in the past.
3) And lastly, but just as important, there's my container of "Super Secret Tomato Food" as seen in the May 31 posting prior to this one. Adding this preparation in every hole is imperative to getting healthy, disease resistant, and very productive tomatoes.
Another trick that I've learned over the years is to lay the larger plants sideways in a trench. Tomatoes shoot-out roots all the way up their stems and you can bury the lower leaves too. Warning: If you plant a tall tomato in a deep hole, the roots will be too deep to absorb any rain or watering with the hose. A good soaking rain shower only absorbs about as far as 6 inches deep, the rest of the soil is still bone dry further down.
Next were the cucumbers. These are an heirloom variety called "National Pickling". As the name implies, these are perfect for making home made pickles. They are just beginning to set out runners and buds. I set out about 30 of these in a long row of raised garden bed. The next step is to put up a fence of deer-netting for them to climb on. 
So off they go in the old wheelbarrow way down to the farthest garden out back.
The first strawberry of the season is ready -want one?
