Syntheses and optical properties of mono- and bis-chromene-annulated meso-arylbacteriochlorins are described. Bacteriochlorins are red and NIR light absorbing chromophores of potential utility in synthetic light harvesting and biomedical applications as photochemotherapeutics or labelling dyes. The report expands the body of work on the optical fine-tuning of synthetic meso-aryl-substituted bacteriochlorins through intramolecular annulation reactions. The regiochemical outcomes of these annulation reactions were investigated using computational tools.  (Hyland, M. A.; Hewage, N.; Panther, K.; Nimthong-Roldán, A.; Zeller, M.; Samaraweera, M.; Gascón, J. A.; Brückner, C. ‘Chromene-annulated Bacteriochlorins’ J. Org. Chem. 2016, accepted for publication 4/14/2016)