Cool weather is very good. Water the plants today so they are fully hydrated before you dig tomorrow. Obviously, it's always best to get as many roots as possible. However, you can actually start tomatoes from cuttings in as little as a week to ten days, so even if you lose some roots, with proper care, the seedlings should be fine. Cut off the lower leaves and plant them deeply into the medium to encourage them to root all along the stem. Dig only a few at a time and work quickly. Water them immediately after you put them in their pots/spot. Keep them in dappled shade for a few days if the sun comes out bright and hot.

Thanks for the tips Donna. Many of the people coming have written in emails how they are trying gardening for the first time. They keep asking me questions. I don't actually like tomatoes so I don't know a lot. But the teacher in me makes me want to learn all about how to transplant tomatoes and teach others how to do it.

DON'T.........LIKE............TOMATOES?????????????????????
AAAAAAUUUUUUGGGGGHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH

I like tomato byproducts such as spaghetti sauce, ketchup, and salsa. Both my husband and I dislike "raw" tomatoes.

Scientists have done studies and discovered a certain percentage (about 10%) of the population dislikes the taste of raw tomatoes. Tomatoes are in the same family as nightshade, which is poisonous. Some scientists believe certain people developed an aversion to the taste of tomatoes as a way staying alive. People just avoided eating anything in the nightshade family whether it was poisonous or not.

I am growing tomatoes this year to make my own salsa and maybe spaghetti sauce. I am sure my husband will use some of the tomatoes in chili. One way or another I will have to learn to can. My mother in law will be very happy to teach me. She's always trying to get me to spend more time in the kitchen. (In my house I grow the food, and my hubby cooks the food.)

Donna is right on.

If your tomatoes are fairly close together, I would dig them up all at once because the roots will all be intertwined.

By digging them up all at once, you can carefully pull the soil away from the roots to free each individual plant. This will help in keeping as many roots as possible.

Like Donna said, cooler weather is best for transplanting - and ensure the plants are well hydrated.

When you transplant the tomatoes to another location, it is perfectly fine to plant them deeper than what they previously were. They will make roots along the stem that was covered up. This also helps to strengthen the plant against harsh winds.

Here is a link that might be useful: BsnTech Gardening Blog

veggiefaery, don't feel bad, I don't like toms either. Shhh! :)
Of course, this comes from someone who also hates chocolate, french fries, chips and ice cream...

One way to help separate clumps of seedlings is to soak the clump in a bit of tepid water. It breaks up the soil mass. With sandy soils, it's pretty instantaneous. With clay soils, you can let them soak for an hour.

Then, gently swish them back and forth, and the soil will fall away,leaving the roots mostly undamaged and making them really easy to separate.

When separated, repot carefully, water deeply, and put them in a coolish, shady, humid place for a few days to recover.

Make sure those people understand that it might take as much as two weeks for the plants to settle in and show growth. I don't know how many of my new community gardeners almost give up just before the change occurs. Also if they get yellow they are overwatering. Don't water for two days and then start slowly again. That's another thing my newbies do. Once they show growth it's time to give them regular fertilizing.

Can you tell folks who come for your tomatoes, what they are? If they grew from hybrid plants that probably isn't possible. If you had a mix of open-pollinated varieties, it could still be a mystery.

Are you really confident that your volunteer tomatoes will have time to mature and ripen a crop there in Wisconsin, zone 4/5?

I supposedly have zone 5 winters but seldom experience a frost-free growing season longer than 150 days (Sunset zone 2). It froze this week.

Volunteer tomatoes seldom ripen and I've allowed them to grow several times. With the short-season varieties that I grow, a volunteer can - at best - produce just 1 or 2 ripe tomatoes before frost kills the plant.

Steve

I live in Wis. in Zone 3 and I often start volunteer tomatoes. Last year I started some romas and got a less than average crop but it was all I needed. This year I think the volunteers will do much better because we have had such warm weather very early. These tomatoes could have as much as a month head start compared to other years here.