This paper analyzes rural-urban disparities in life expectancy with and without pain among upper-middle age and older adults. Data are from the nationally representative Health and Retirement Study, 2000–2018, N = 18,160, age 53+. Interpolated Markov Chain software, based on the multistate life tables, is used to calculate absolute and relative pain expectancies by age, sex, rural-suburban-urban residence and U.S. regions. Results show significant rural disadvantages versus those in urban and often suburban areas. Example: males at 55 in rural areas can expect to live 15.1 years, or 65.2 percent pain-free life, while those in suburban areas expect to live 1.7 more years, or 2.6 percentage points more, pain-free life and urban residents expect to live 2.4 more year, or 4.7 percentage points more. The rural disadvantage persists for females, with differences being a little less prominent. At very old age (85+), rural-urban differences diminish or reverse. Rural-urban pain disparities are most pronounced in the Northeast and South regions, and least in the Midwest and West. The findings highlight that rural-urban is an important dimension shaping the geography of pain. More research is needed to disentangle the mechanisms through which residential environments impact people's pain experiences.