|Founder||Colin Sargent and Nancy Sargent|
|First issue||April 1986|
|Based in||Portland, Maine|
Founded in October 1985 by Colin Sargent and Nancy Sargent of Sargent Publishing, Inc., it has featured notable writers such as Pulitzer Prize winner Louis Simpson, Frederick Barthelme, Jason Brown, C. D. B. Bryan, Brian Daly, Dan Domench, Tess Gerritsen, Ann Hood, Sebastian Junger, Barbara Lefcowitz, Diane Lefer, Tomislav Longinovic, Mameve Medwed, Rick Moody, and Janwillem van de Wetering.
Another 1980s feature, "Pizza Diplomacy", reported crews from Glasnost-era Soviet fishing trawlers off the coast of Maine were radioing in orders for pizzas in Rockland, and having them sent out in launches. Portland Magazine writer Kevin LeDuc went out with a pizza order, interviewed crew members, and photographed the captain in his cabin.
In recent years, the perfect-bound glossy has regularly eclipsed 200 pages. A strong emphasis on dramatic photography and interviews with prominent Mainers including Patrick Dempsey, Liv Tyler, Stephen King, Rachel Nichols, Seth Wescott, Ian Crocker and more and has resulted in 40 American Graphic Design awards in 2007-2008. Portland Magazine is a grand prize winner for Best Cover at the Maggie Zine Awards sponsored by Newsstand Resource.
In June 2017, Portland Magazine set an all-time record with a page count of 304 in their Summerguide 2017.
The magazine holds the registered U.S. trademark Portland Monthly from the U.S. Patent & Trademark Office, as well as the domain www.portlandmonthly.com.
- October 1985: Portland Magazine founded. First issue sets record at Portland News for single-copy sales of a premiere issue.
- April–July 1986: Waterfront series by John Taylor wins First Prize for Magazine Feature Writing in award ceremony conducted by the American Society of Business Communications.
- June 1986: Magazine is profiled on television news by WGME-TV as one of three successful new small businesses in Maine. Feature articles on magazine printed in The Hartford Courant and the Maine Sunday Telegram.
- August 1987: Cover story breaks the news that van Gogh’s Irises painting is about to be sold, forcing Sotheby's to confirm this story to other media at a press conference in September.
- December 1988: Stephen King ends five-year silence with regional magazines. In a controversial interview in Portland Magazine, he calls Portland a “blow-dry, Perrier, Mazda type of city”. Record newsstand sales.
- September 1989: Jamie Wyeth interview appears with photos by Life magazine photographer Susan Gray. Interview draws praise from Andrew Wyeth.
- January 1990: Portland Public Library allocates funds to hard-bind Portland Magazine as part of its permanent collection of magazines.
- April 1990: Fiction by Pulitzer Prize winner Louis Simpson.
- July 1990: Hannaford Brothers starts a program to provide new company executives with copies of the magazine.
- March 1991: Five-year-old Portland Magazine wins newsstand distribution on major newsstands in New York, Boston, Hartford, Providence, Worcester, Newport, Lawrence, Lowell, and the Massachusetts North Shore.
- April 1991: The New York Public Library, praising the magazine for “original regional coverage and literary merit,” purchases the entire back list for its permanent collection.
- July 1992: Two major Canadian bookstore chains begin distributing Portland Magazine.
- October 1992: Reader's Digest, Inc., contracts with Portland Magazine to sell subscriptions nationwide through its QSP program.
- July/August 1993: Fiction by Sebastian Junger, author of The Perfect Storm.
- October 1996: Portland Magazine is featured nationwide on ABC’s The Rosie O'Donnell Show.
- December 2002: Picked up by Amazon.com.
- December 2003: Annual subscription record broken by 44 percent as Portland Magazine enters its 19th year.
- September 2004: Magazine growing at 47 percent, sets records New England-wide.
- June 2005: Portland Magazine is the winner of both Best Cover and Best of the Show awards at the Maggie Zine Cover Award Competition, conducted in Greensboro, North Carolina, by NewsStand Resource. The cover took first place nationally in the City, Regional, and Special magazine category for achievement in art direction and newsstand appeal, and then as a capping honor was chosen to be the Grand Prize Winner as Best of the Show. "We had 500 entrants in the cover competition, including National Geographic, U.S. News & World Report, Scientific American, Nickelodeon Magazine, Pittsburgh Magazine, and out of all of them Portland Magazine had the best cover," says Frances Becker Cliff, publisher of NewsStand Resource, the nation's leading trade magazine for single-copy newsstand sales. “"We love it. It's just Maine, you know? It says Maine."
- August 2005: Mediabistro.com, the international consortium for media followers, praises Portland Magazine for "high caliber" content "in the vein of Pulitzer Prize winner Louis Simpson, Frederick Barthelme, and Barbara Lefcowitz...in addition to the standard city-mag fare...indeed the magazine reaches beyond the usual..." -www.mediabistro.com
- June 2006: Portland Magazine wins a second national award for cover art direction presented at the Maggie Zine Cover Award Competition from NewsStand Resource in the City, Regional, and Special magazine category.
- Summerguide 2006: Award-winning author Rick Moody-of Garden State, The Ice Storm, and The Black Veil fame-writes Lamoine for the magazine's fiction feature.
- August 2006: Portland Magazine is profiled as one of the top-tier commercial magazines in the country for savvy mediaphiles to follow and submit their work to mediabistro.com, international media consortium.
- March 2007: Portland Magazine wins an unprecedented third national award for cover art direction presented at the Maggie Zine Cover Award Competition from NewsStand Resource in the City, Regional, and Special magazine category.
- July 2007: 224-page Summerguide 2007 eclipses all records for a magazine published in Portland. Portland Magazine chosen to be complimentary passenger selections on JetBlue Airways, Amtrak Downeaster, and premier business-travel clubs in all major airports in the Northeast.
- September 2007: Portland Magazine wins eight prizes at the American Graphic Design Awards by Graphic Design USA magazine and sponsored by Adobe Systems Incorporated. Winning designs included February/March 2007-Publication Design, December 2006-Cover Design, Winterguide 2007-Cover Design, "Who Is That Guy?" [November 2006]-Editorial Design, "Vanishing Point" [Winterguide 2007]-Editorial Design, "Tall Order" [Winterguide 2007]-Editorial Design, "Tasty Maine" [December 2006]-Editorial Design, and "How Clean Is Portland Harbor?" [Dec. 2006]-Editorial Design.
- November 2007: Portland Stage praises "the diversity of the articles and features in Portland Magazine-truly a champion of the arts."
- September 2008: Portland Magazine captures five prizes at a nationwide juried competition from one of the most respected design industry resources, the prestigious national American Graphic Design Awards for design excellence conducted in New York by Graphic Design USA magazine. Winning designs included Summerguide 2007-Cover Design, May 2007-Cover Design, April 2007-Cover Design, "We'll Leave a Light On for You" [September 2007]-Editorial Design, and "Dream a Little Dream" [Winterguide 2008]-Editorial Design.
- Graphic Design USA, New York: Graphic Design USA
- NewsStand Resource, Greensboro: NewsStand Resource
- State of Maine Government.
- Pulitzer Prize.
- Portland Monthly Publication.
- Van Gogh Gallery -- Iris painting
- Pizza Diplomacy, Life on a Soviet Freighter
- Graphic Design USA