In the late 1800s, Lake Oswego was a place where people actually worked for a living, home to the first iron furnace on the West Coast. After the iron industry collapsed, Lake Oswego was rebranded first as a weekend getaway for Portland's wealthiest citizens, and later as a year-round luxury property development where the city's elite could "live where they play." Today, its transformation from blue-collar pioneer outpost is complete, to an eclectic collection of multimillion-dollar lakefront luxury homes, quaint cottage villages, and a planned community on the summit of a dormant volcano.
Only a few minutes away from Portland's city center, Lake Oswego is consistently ranked as one of the most desirable places in Oregon to live, due in no small part to the unabashed sense of exclusivity. A running joke among Portland natives holds that Lake Oswego doesn't need gated communities, because it already constitutes one giant gated community. And you gotta pay to play there, baby. Even the eponymous private lake is accessible only to members of the nonprofit Lake Oswego Corporation, which employs a private security force tasked with ejecting, and until very recently, even arresting outsiders bold enough to trespass its hallowed waters. More like Lake Offyougo, amirite? -- Kashann Kilson, Thrillist contributor