Portland! No longer just for hipsters only, this city's got cold brews (craft beer and iced coffees) and a hot local food and shopping scene, all of which make it an easy-to-love backdrop for catching up with friends.
Portland was almost "Boston, Oregon"! Portland was named by the flip of a coin by its two original settlers, Asa Lovejoy and Francis W. Pettygrove. Lovejoy wanted to name the new settlement after his hometown of Boston; Pettygrove wanted to name it after his hometown of Portland, Maine. Pettygrove won the coin toss, best 2 out of 3.