Hakodate is a strange place. It doesn't take long when walking through the city to see the abundance of Western influenced architecture that makes up both its residential and business districts. The city was the first in Japan to open ports for trade with the world. There are a number of well preserved historical locations, like the former British and Russian consulates as well as a variety of churches, that were established after the country opened its doors to the world. However, leaving the downtown area and wandering the outskirts of local neighborboods like Sumiyoshi and Yachigashira in southern Hakodate show a look more in line with the rest of Japan.
Buildings cover the tiny peninsula all the way to the base of Mt. Hakodate, which provides one of the best cityscape night views I've ever seen. The line for the cable car up to the summit's observatory can get really long as evening approaches. Best to get up there early, wait for the sun to set and take in the bright lights of the city below.