East Street is also a sweet ride from Perrysville. I live up here and that is my route 90% of the time into town. I can stay in the aerobars all the way into northside and pass cars (who actually obey the speed limit along there).
It is not crazy steep like the other hills, but very well lit at night and its the least painful way up to Observatory Hill.
The other fun way to get up here is taking the west end bike trail to ALCOSAN, and coming up the back way through Woods Run and then into Riverview Park on Kilbuck Rd (which is closed to cars). Very dark at night, but peaceful. Probably not a good idea when you are alone though. This area of town is not known for its tranquility let's just say...