You can check the grind by just sifting the grain through your fingers. If there are many whole, half, or quarter grains you need it finer.
A thought here is that instead of letting the bag drip you should press it. Since it seems the method is similar to wine making and in that scenario they would use a hand or bladder press to get as much liquid as possible out of the grain. A simple drip rest will get relatively little additional wort.
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In Primary: KSS-Fool's Folly
In Secondary:Old Croaker Imperial Stout
Long Aging: Old Bruin, Flanders Red Ale, Flanders Pale Ale, Wheat'n'Peach, TC- Aged Amber, TC-Aged Pale Wheat, pSaison Historiq, Black Bretty, Flanders Red Rye
On Tap: TC-Red Headed Stepchild, TC-Saison v4, TC-Misty Moorings,
Bottled: Thunderhead Imperial Stout, TC-Three Weissmen
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