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):

doleful
    adj 1: filled with or evoking sadness; "the child's doleful
           expression"; "stared with mournful eyes"; "mournful news"
           [syn: doleful, mournful]

Moby Thesaurus II by Grady Ward, 1.0:

60 Moby Thesaurus words for "doleful":
   affecting, afflicted, aggrieved, anguished, blue, careworn,
   cast down, cheerless, crestfallen, dejected, depressed, depressing,
   disconsolate, dispirited, distressed, distressing, dolorous, down,
   down-in-the-mouth, downhearted, dreary, dumb with grief, forlorn,
   funereal, gloomy, grief-stricken, griefful, grieved, grieving,
   grievous, harrowing, heartrending, in grief, joyless, lamentable,
   lugubrious, melancholy, miserable, mournful, mourning, moving,
   pathetic, piteous, pitiable, pitiful, plaintive, plangent,
   plunged in grief, rueful, ruthful, sad, sorrowed, sorrowful,
   sorrowing, tearful, touching, unhappy, woebegone, woeful,
   wretched