We describe the design and measurement of feedhorn-coupled, transition-edge sensor (TES) polarimeters with two passbands centered at 220 GHz and 280 GHz, intended for observations of the cosmic microwave background. Each pixel couples polarized light in two linear polarizations by use of a planar orthomode transducer and senses power via four TES bolometers, one for each band in each linear polarization. Previous designs of this detector architecture incorporated passbands from 27 GHz to 220 GHz; we now demonstrate this technology at frequencies up to 315 GHz. Observational passbands are defined with an on-chip diplexer, and Fourier-transform-spectrometer measurements are in excellent agreement with simulations. After accounting for expected losses in our detector system, we find coupling from feedhorn to TES bolometer using a cryogenic, temperature-controlled thermal source is as expected. Relative to a detector with no losses and the designed passbands, our device is 95% (86%) efficient in the 220 (280) GHz band. Lastly, we compare two powertermination schemes commonly used in wide-bandwidth millimeter-wave polarimeters and find equal performance in terms of optical efficiency and passband shape.The cosmic microwave background (CMB) provides a powerful probe of the earliest moments of the universe. Precision measurements of CMB temperature and polarization anisotropies have played a crucial role in shaping our understanding of how the universe formed by providing rigorous constraints [1] on parameters of the standard cosmological model, Λ CDM. However, millimeter-wave observations are complicated by the presence of astrophysical foregrounds, such as synchrotron emission and galactic dust, which also radiate at