The solvent-dependent ground-state conformational equilibrium and excited-state dynamics of 2-(2‘-hydroxyphenyl)benzoxazole have been characterized in several solvents on the femtosecond to nanosecond time scales. The only observable ground-state tautomer is the enol, which exists in equilibrium between the syn- and anti-rotational isomers. In the anti-enol isomer, the phenyl hydroxyl group appears to not interact strongly with solvent but rather forms a strong intramolecular hydrogen bond with the benzoxazole oxygen atom. In the syn-enol isomer, the phenyl hydroxyl proton may interact with solvent or form an internal hydrogen bond with the benzoxazole nitrogen atom. Upon excitation, the proton is transferred from the oxygen atom to the nitrogen atom of the internally hydrogen bonded syn-enol isomer in 170 fs, regardless of the solvent. The lifetime of the resulting excited keto tautomer is solvent dependent and on the order of picoseconds. In addition to these dynamics, several additional dynamic process...