"This Portland staple was originally founded in 1935 and is heavily sought after for its James Beard-endorsed burger. Skyline has a 1950s diner feel inside, as well as a large back outdoor patio for nice days. Skyline serves classic milkshake flavors, but also serves such flavors as caramel apple and chocolate-covered cherry, for something off the beaten track. Fuller’s pie shakes, with flavors like fresh banana cream pie and coconut cream pie, are particularly thick, delicious concoctions. If one is really hungry, a giant 30-ounce shake is also available." - Maya MacEvoy