First time haying

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A lot of balers have moisture meter's on them to tell you the moisture content of the hay. You can also check the moisture content of the hay before baling/rolling with a moisture meter.

I would add, if you have any suspicion that the moisture content is too high after it is baled, do not put those bales in a barn. Every year a lot of barns burn because of this.
Ended up getting a long soil thermometer and taking the bales temps, from what it says online anything below 130 degrees should be fine to put in the barn. Had some above that so just letting them cure.
Another thing to watch out for, anywhere that is shaded part of the day, like along hedgerows, will stay wet much longer than the rest of the field. If at all practical, that is better saved for the next day. Though we did small squares for horse people, so sometimes we just baled and tossed the bale or two from that part on the compost pile, or fed right away, depending on the details of the situation.

When baling, watch out for dew, or even just the cooling down at the end of the day bringing moisture back out of the air. There'd usually come a time on baling day between 6:30 and 7:30 that the moisture would go back into the hay. It got tougher, bales got heavier, and usually everything baled after that point molded. Unless it's going to rain, bale it tomorrow.

Speaking of rain, it's not necessarily an issue, depending on how much, and how recently it was cut. The same amount of rain that would ruin hay on bale day would be just fine if it wasn't too long after cutting and the hay didn't dry out yet.

Tedding also works wonders when you have good drying weather. We've cut and baled same day on rare occasion. Definitely helps keep the hay from bleaching, but the weather has to be hot enough, dry enough, and breezy enough, and you have to run the tedder through it 3 or more times, but if you have the help available or small enough fields, it makes some really nice hay.

As for knowing if it's ready, I like to grab a pinch and taste it. Kind of hard to explain, but if you've chewed on a bunch you'll know what too dry, too wet, or too dusty will feel and taste like. I've found if it tastes good to me, my handful of cattle will eat it up and yell for more. If I can't stand chewing on it for a few minutes, neither can they and it winds up all over the place and most is wasted.
There is a sweet medium for baling hay. Molded hay usually started molding before it was baled. Mold spores don't penetrate hay bales and find the middle of the bale to sprout, they need oxygen and moisture to survive. Heavy or thick hay needs to be turned over for it to dry. It can be dry on top but damp and moldy near the ground. Baled green grass is silage and as long as it is tightly packed and or wrapped in plastic controlling the oxygen, it ferments but doesn't mold. I have baled damp rice straw that nothing short of starvation could get anything to eat it but after it fermented, they fought over it.

Too dry is bad as well. you will lose a lot of the leafy part of the grass out of the bottom of the baler and end up with a bunch of stalks. You also run the risk of a fire from the smallest of a spark, I caught hay on fire once because I got too close to a gravel road with the rake, and it sparked on the gravel. I baled at night after that until the moisture got too high. Usually, the pick-up will begin to clog if the moisture is too high.
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Get yourself a moisture tester if you are just starting out. After a while you will get a feel for when the hay is the right dryness to bale by hand. You want it about 12-17% moisture for dry hay.

The Vee rakes tend to dump hay to the middle of the row, but the hay in the middle doesn't get turned over to dry. Many models have a center kicker wheel option that will turn up the hay right in the middle. They are beneficial.

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