If we want to feel the sense of a place; if we desire to experience the immediacy of a place, Painting of Gustave Caillebotte titled as Paris Street in Rainy Weather is one of the best sources. When an artist takes pen or pencil in hand, first thing he remembers is the scenes in immediate surrounding. There can hardly be better and easily available subjects for painting other than our own street or the road on which we drive daily. The European artists have chosen the same. They paint cities and towns since the culture of cities has evolved.
The Feeling: While standing on a street an artist would find the structure of buildings and level of sunlight falling on the place an alluring one. The lighted area and shadows would appeal the artist and he would be tempered to make out a painting that would represent the feeling he encountered. Resultant painting would essentially be the feeling of the artist while being on the pavement of street. For an artist, it would not be like a photographic representation of a scene; it would be mirror of the pleasure and the feeling he has gone thorough. And that is the real challenge before an artist who likes painting streets and towns.
Sketch: First thing an artist would think about would be making out a sketch of the cityscape pulsating before his or her eyes. There would be people; there would be animals; there would be mood of the air; and there would be signatures of seasons. All these would impress upon the artist and resulting sketch would be an immediate recording what he sees and feels. If it is day time, the most important aspect would be the recording of effect of light: the direction of light, the intensity of light and the visual impressions the light is making on each object on which it falls. The sketch would take care of these things.