 The magazine won three awards in the City and Regional Magazine Association 's 20th Annual National City and Regional Magazine Awards in 2005 , receiving recognition in Civic Journalism , Excellence in Writing and General Excellence . The magazine was one of three companies nominated by the Oregon Entrepreneurs Forum as a finalist for Working Capital Stage Company of the Year . In 2006 Portland Monthly was a finalist for " Best Overall Design " of a consumer magazine , in the Folio : Gold Ozzie Awards . In her 2007 book Insiders ' Guide to Portland , Oregon , author Rachel Dresbeck wrote that the magazine " maintains an excellent calendar " of events going on in the city . In July 2007 Nicole Vogel was a finalist among nominees for an individual entrepreneurship award from the Oregon Entrepreneurs Network . 
