Vowels vary in their acoustic similarity across regional dialects of American English, such that some vowels are more similar to one another in some dialects than others. Acoustic vowel distance measures typically evaluate vowel similarity at a discrete time point, resulting in distance estimates that may not fully capture vowel similarity in formant trajectory dynamics. In the current study, language and accent distance measures, which evaluate acoustic distances between talkers over time, were applied to the evaluation of vowel category similarity within talkers. These vowel category distances were then compared across dialects, and their utility in capturing predicted patterns of regional dialect variation in American English was examined. Dynamic time warping of mel-frequency cepstral coefficients was used to assess acoustic distance across the frequency spectrum and captured predicted Southern American English vowel similarity. Root-mean-square distance and generalized additive mixed models were used to assess acoustic distance for selected formant trajectories and captured predicted Southern, New England, and Northern American English vowel similarity. Generalized additive mixed models captured the most predicted variation, but, unlike the other measures, do not return a single acoustic distance value. All three measures are potentially useful for understanding variation in vowel category similarity across dialects.