On July 20, 1990, the north edge of the Gulf Stream (36.7¿N, 72.0¿W) was sampled by the R/V Cape Henlopen and simultaneously imaged by the Jet Propulsion Laboratory's airborne synthetic aperture radar (SAR). Hydrographic measurements show an abrupt surface front separating warm, salty Gulf Stream water in the south from a filament of cool, fresh (<33 practical salinity unit (psu)) water to the north. The filament lies within the stream and is likely water entrained from the continental shelf. The southern boundary of the filament is marked by increased surface wave breaking in a 100- to 200-m-wide zone, accumulations of Sargassum, and an orthogonal velocity change of 20 cm/s. The front is manifested in a sequence of SAR images as a narrow line having returns 1--2 dB higher than background. (A second, transient SAR line occurs near the northern filament boundary.) The observations are compared with model calculations of the surface wave hydrodynamics and radar scattering. The ocean waves are driven by southwesterly 8-m/s winds and interact with the front to produce primarily an enhancement of 2- to 3-m waves over a ≲200-m-wide region centered downwind of the front. Using a composite scattering radar model along with measured breaking-wave statistics, we show that the observed modulations in the radar backscatter can be accounted for through breaking-wave and tilted Bragg wave scattering effects. These results further show that SAR images of the ocean surface can be exploited for detailed study of particular ocean processes.