1 8 6 0 s , ▁during ▁the ▁Civil ▁War , ▁Confeder ate ▁soldiers ▁were ▁thought ▁to ▁use ▁the ▁cave ▁as ▁a ▁rende z vous ▁point . ▁ ▁After ▁the ▁Civil ▁War , ▁Missouri ▁became ▁a ▁center ▁of ▁win em aking ▁in ▁the ▁Mid west . ▁In ▁ 1 8 6 6 , ▁the ▁Cl iff ▁C ave ▁W ine ▁Company ▁was ▁established ; ▁in ▁ 1 8 6 8 , ▁they ▁purchased ▁the ▁area ▁for ▁$ 3 6 , 1 7 6 ▁to ▁use ▁the ▁cave ▁as ▁a ▁natural ▁wine ▁cell ar . ▁The ▁company ▁plant ed ▁twenty - five ▁acres ▁of ▁g rap es ▁in ▁the ▁area ▁which ▁produced ▁ 3 , 0 0 0 ▁gall ons ▁of ▁wine ▁in ▁one ▁year . ▁The ▁company ▁itself ▁had ▁ 2 4 0 ▁acres ▁of ▁v ine yard ▁along ▁the ▁Mississippi ▁River , ▁and ▁by ▁ 1 8 7 0 , ▁the ▁cave ▁had ▁a ▁storage ▁capacity ▁of ▁ 1 0 0 , 0 0 0 ▁gall ons ▁of ▁wine . ▁Stone work ▁near ▁the ▁cave ▁entrance ▁added ▁in ▁this ▁time ▁still ▁exists ▁today . ▁ ▁In ▁the ▁late ▁ 1 8 0 0 s , ▁volunte er ▁soldiers ▁from ▁Jefferson ▁Bar ra cks ▁built ▁a ▁sal oon ▁in ▁the ▁cave ▁entrance . ▁In ▁approximately ▁ 1 9 1 0 , ▁the ▁cave ▁was ▁le ased ▁to ▁An he user - Bus ch ▁to ▁store ▁be er , ▁with ▁the ▁company ▁har vest ing ▁ice ▁from ▁the ▁river ▁in ▁the ▁winter ▁to ▁keep