▁many ▁slave own ers ▁to ▁free ▁their ▁slaves ; ▁half ▁of ▁the ▁state ' s ▁black ▁population ▁was ▁free ▁by ▁ 1 8 1 0 , ▁and ▁more ▁than ▁ 9 0 % ▁were ▁free ▁by ▁ 1 8 6 0 . ▁This ▁tr end ▁also ▁led ▁pro - s la very ▁legisl ators ▁to ▁restrict ▁free ▁black ▁organizations , ▁and ▁the ▁const ab ul ary ▁in ▁Wil ming ton ▁was ▁accused ▁of ▁har sh ▁enfor cement ▁of ▁run away ▁slave ▁laws ▁while ▁many ▁Del aware ans ▁kid n apped ▁free ▁black s ▁among ▁the ▁large ▁communities ▁throughout ▁the ▁state ▁and ▁sold ▁them ▁to ▁plant ations ▁further ▁south . ▁ ▁During ▁the ▁Civil ▁War , ▁Del aware ▁was ▁a ▁slave ▁state ▁that ▁remained ▁in ▁the ▁Union . ▁( Del aware ▁vot ers ▁voted ▁not ▁to ▁se ced e ▁on ▁January ▁ 3 , ▁ 1 8 6 1 .) ▁Del aware ▁had ▁been ▁the ▁first ▁state ▁to ▁em brace ▁the ▁Union ▁by ▁rat ifying ▁the ▁Constitution , ▁and ▁would ▁be ▁the ▁last ▁to ▁leave ▁it , ▁according ▁to ▁Del aware ' s ▁governor ▁at ▁the ▁time . ▁Although ▁most ▁Del aware ▁citizens ▁who ▁fought ▁in ▁the ▁Civil ▁War ▁served ▁in ▁reg iments ▁on ▁the ▁Union ▁side , ▁some ▁did , ▁in ▁fact , ▁serve ▁in ▁Del aware ▁companies ▁on ▁the ▁Confeder ate ▁side ▁in ▁the ▁Maryland ▁and ▁Virginia ▁Reg iments . ▁ ▁Del aware ▁was ▁the ▁one ▁slave ▁state ▁from ▁which ▁the ▁Confeder ate ▁States ▁of ▁America ▁could ▁not ▁rec ruit ▁a ▁full