TRIPPy (TRailed Image Photometry in Python) uses a pill-shaped aperture, a rectangle described by three parameters (trail length, angle, and radius) to improve photometry of moving sources over that done with circular apertures. It can generate accurate model and trailed point-spread functions from stationary background sources in sidereally tracked images. Appropriate aperture correction provides accurate, unbiased flux measurement. TRIPPy requires numpy, scipy, matplotlib, Astropy (ascl:1304.002), and stsci.numdisplay; emcee (ascl:1303.002) and SExtractor (ascl:1010.064) are optional.