How many tomatoes can my plant handle

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I'm a newbie to gardening and this is my first attempt to grow tomatoes. I planted a Hillbilly heirloom plant this spring without reading what to do, so instead of trimming it to a single main stalk, there are 5 stalks rising from the bottom and the entire plant has become quite crowded. I've been pruning branches every few days to allow some air circulation and light. It's now the end of August, so where I live in Connecticut, there's not going to be enough time for new fruit to fully mature, so I've pinched off all the suckers and flowers. I'd like the existing fruit to grow to a good size, so I'm wondering if I should also prune some of the latest fruit to emerge that are still tiny. I have 23 tomatoes that are getting to be decent size and another 11 tiny ones. Is this too much for a single plant to handle or should I leave it with all the fruit? Thanks for any advice.
 
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Hillbillies can grow to over 2lbs each, that's potentially 50lbs of tomatoes so far.

I'd look at thinning them out and making sure what's there is well supported.

My biggest problem with them was a tendency to split the skins after a heavy rain. Especially as they got close to ripe. If you can control the water you can be successful.
 
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Now that some of the tiny ones are growing, I see 36 tomatoes. I've read that this variety can produce tomatoes weighing 1-2 pounds each. Should I expect mine to be smaller since there are so many? Would it be better to remove some?
Hillbillies can grow to over 2lbs each, that's potentially 50lbs of tomatoes so far.

I'd look at thinning them out and making sure what's there is well supported.

My biggest problem with them was a tendency to split the skins after a heavy rain. Especially as they got close to ripe. If you can control the water you can be successful.
Thank you, RudeRunner for the advice. I've been trying to have them get a consistent amount of water, but it seems that this summer the weather forecast has often been pretty inaccurate in terms of rainfall, so there are times that I water the plant and it gets more rain than predicted later in the day.Oh, well. I'll look closely today and decide which tomatoes to thin, but it will be difficult removing perfectly good fruit.
 
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36 tomatoes on one plant or how many plants?

Yes it is a quality vs quanity thing but it is a vague kind of calculation depending on what they are, your area, and how you grow them. I usually double stem my indeterminates/semis mainly for airflow and nutrient division from the root and that takes care of how many tomatoes the plant will grow automatically for me. Determinates do not seem to produce that well here.

Each variety of tomato does have its quirks about splitting or catfacing or production in your area or climate so what grows best for one person does not for another.
 
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I had 36 on the 5 stems of one plant, but I've just reduced that to 29 by removing the highest ones that are difficult to support. The plant was about 7 feet tall and it was difficult to rig up support for the highest branches and tomatoes, so I've topped it off around 6 feet. I am growing it in a small raised bed that I built that is about 3'x4.5'.
 
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The biggest hillbilly I successfully grew was 2.5lbs., many in the 1.5 to 2 range. They're known for size and colors.

I typically grow tomatoes along a fence or trellis so I have lots of places to tie to for support. For really large tomatoes, you might even make a sling to support the tomato itself.

You're looking at 30 to 60 lbs, I'd be deliberate about cutting suckers and keeping the plants under control.

My situation is different in that I have a larger area and sporadic rainfall. Your smaller bed would be easier to cover. Like I said, jy problem was splitting after a heavy rain, you could put up a canopy to protect your plant from that and water as needed. Pop up canopies aren't expensive and are probably on clearance sales now that the end of the summer is approaching.
 

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