A walk down Main Street can be very much like a stroll through a museum gallery--visually rich, inviting unexpected choices, aesthetically rewarding. This article explores the concept of shop windows as visually ordered compositions, much like paintings and other art objects, and suggests some approaches to applying this concept in teaching a range of subjects and styles of art in both classrooms and actual museums. For the purposes of argument, the author will assume that the mythical Main Street is alive with businesses of many kinds, with the old-fashioned windows open to the street that allow people to "window shop" for many blocks. Some examples are drawn from the very enjoyable experience they still offer, of wandering from image to image, commenting as they go. The parallels between the museum experience and the window-shopping experience of pedestrians in downtown streets suggest some fairly exciting connections for art educators--and, more importantly, for their students, who are already experiencing downtown and who may welcome bridges to the art museum at the end of the street. (Contains 14 endnotes.)