The Collaborative International Dictionary of English v.0.48:

Doleful \Dole"ful\, a.
   Full of dole or grief; expressing or exciting sorrow;
   sorrowful; sad; dismal.
   [1913 Webster]

         With screwed face and doleful whine.     --South.
   [1913 Webster]

         Regions of sorrow, doleful shades.       --Milton.

   Syn: Piteous; rueful; sorrowful; woeful; melancholy; sad
        gloomy; dismal; dolorous; woe-begone. -- Dole"ful*ly,
        adv. -- Dole"ful*ness, n.
        [1913 Webster]

WordNet (r) 3.0 (2006):

dolefully
    adv 1: with sadness; in a sorrowful manner; "his mother looked
           at him dolefully when he told her he had joined the Army"
           [syn: dolefully, sorrowfully]