The proton transfer reaction between CHCl₃ and CH₃O^– is investigated at the B3LYP/6-31+G(d,p) level. The proton transfer process is modeled in a microsolvated methanol environment, CH₃Cl + CH₃O^–(CH₃OH)_n, where, n = 0, 2–6, 8. Comparisons to a polarized continuum model indicate that the microsolvated calculations do a better job of reproducing experimental results, and it is observed that the relative stability of the methoxide ion is affected by the number of solvating methanol molecules which surround it. For each experiment, the solvent system is increased by one molecule or two molecules of methanol, and the relative energies of each state of the proton in flight are calculated and compared. For n = 0, there is a single well and proton transfer from chloroform to methoxide is exothermic. For n = 2, there is a double well and proton transfer is endothermic. For n > 2, there is a single well and proton transfer is endothermic. We report here the simplest possible models of a solvent cluster to approximate this proton transfer reaction in methanol solution.