Lewis & Short

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The word maestissimum could not be parsed. Trying a normal dictionary lookup:

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maestĭfĭco (moest-), āvi, ātum, 1, v. a. [maestus-facio], to make sad or sorrowful, to sadden (post-class.): si paupertas angit, si luctus maestificat, Aug. Ep. 121: facies umbris maestificata larvalibus, Sid. Ep. 3, 13 med.; Mart. Cap. 9, § 888.

maestĭfĭcus, a, um, adj. [maestus-facio], saddening (eccl. Lat.) [Fulg.], Serm. 14.

maestĭter (moest-), adv., v. maestus fin. B.

maestĭtĭa (moest-), ae, f. [maestus], a being sad or sorrowful, sadness, sorrow, grief, dejection, melancholy (class.): ex maestitiā, ex hilaritate, ex risu, etc., Cic. Off. 1, 41, 146: totis theatris maestitiam inferre, id. Tusc. 1, 44, 106: esse in maestitiā, id. Phil. 2, 15, 37: maestitiae resistere, id. Or. 43, 148: sapientia est una, quae maestitiam pellat ex animis, id. Fin. 1, 13, 43: illa maestitia est, caruisse anno circensibus uno, Juv. 11, 53.
Of inanim. things, gloom, gloominess, severity: orationis, Cic. Or. 16, 53: frigorum, Col. 7, 3, 11.

maestĭtūdo (moest-), ĭnis, f. [maestus], sadness (ante- and post-class., for maestitia), Att. ap. Non. 136, 24 (Trag. Rel. v. 616 Rib.): ego sum miser, cui tanta maestitu do obtigit, Plaut. Aul. 4, 10, 1; Cael. Aur Tard. 1, 4, 104; Sulp. Sev. Ep. 2, 2: captivitatis maestitudinem (societate) consolari, Pall. 1, 26, 2: animi, Ambros. de Vid. 6, 36.

maestus (moest-), a, um, adj. [maereo, q. v.], full of sadness, sad, sorrowful, afflicted, dejected, melancholy (class.).

  1. I. Lit.: quid vos maestos tam tristesque esse conspicor? Plaut. Bacch. 4, 4, 18: id misera maestast, sibi eorum evenisse inopiam, id. Rud. 2, 3, 67; Cic. Div. 1, 28, 59: cum immolanda Iphigenia tristis Calchas esset, maestior Ulixes, etc., id. Or. 22, 74: maestus ac sordidatus senex, id. de Or. 2, 47, 195; id. Fam. 4, 6, 2: maestus ac sollicitus, Hor. S. 1, 2, 3: maestissimus Hector, Verg. A. 2, 270.
    Of inanim. and abstr. things: maesto et conturbato vultu, Auct. Her. 3, 15, 27: maesta ac lugentia castra, Just. 18, 7: maestam attonitamque videre urbem, Juv. 11, 199: maesta manus, Ov. F. 4, 454: horrida pro maestis lanietur pluma capillis, id. Am. 2, 6, 5: comae, id. F. 4, 854: collum, id. Tr. 3, 5, 15: timor, Verg. A. 1, 202.
    Poet., with inf.: animam maestam teneri, Stat. Th. 10. 775.
  2. II. Transf. (poet. and in post-Aug. prose).
    1. A. Like tristis, gloomy, severe by nature: ille neci maestum mittit Oniten, Verg. A. 12, 514 (naturaliter tristem, severum, quem Graeci σκυθρωπὸν dicunt ἀγέλαστον, Serv.): tacitā maestissimus irā, Val. Fl. 5, 568: oratores maesti et inculti, gloomy, Tac. Or. 24.
    2. B. In gen., connected with mourning; containing, causing, or showing sadness; sad, unhappy, unlucky: vestis, a mourning garment, Prop. 3, 4 (4, 5), 13: tubae, id. 4 (5), 11, 9: funera, Ov. F. 6, 660; cf.: ossa parentis Condidimus terrā maestasque sacravimus aras, Verg. A. 5, 48: a laevā maesta volavit avis, the bird of ill omen, Ov. Ib. 128: venter, exhausted with hunger, Lucil. ap. Non. 350, 33 (enectus fame, Non.).
      Hence, adv., in two forms.
    1. * A. maestē, with sadness, saaly, sorrowfully: maeste, hilariter, Auct. Her. 3, 14, 24.
    2. * B. maestĭter, in a way to indicate sorrow: maestiter vestitae, Plaut. Rud. 1, 5, 6.