Founded in 1862, its roots extend to Maine’s earliest newspapers, the Falmouth Gazette & Weekly Advertiser, started in 1785, and the Eastern Argus, first published in Portland in 1803.

[3] Its first issue, published on June 23, 1862, announced strong support for Abraham Lincoln and condemned slavery as "the foulest blot upon our national character.

Gannett officials cited shared values; the Times Company was also a family-owned business, and its owners, the Blethen family, had roots in Maine.

[9] The Press Herald and its sister publications were reorganized as Blethen Maine Newspapers, an independent division of The Seattle Times Company.

[17] After more than a year on the market, on June 15, 2009, the papers were sold to MaineToday Media, Inc., headed by Richard L. Connor, publisher of Times Leader in Wilkes-Barre, Pennsylvania, with financing from HM Capital Partners and Citizens Bank.

[21] As part of the sale, Portland Newspaper Guild members took a 10% pay cut in exchange for 15% ownership in MaineToday Media.

[23] "Many saw Saturday's front-page story and photo regarding the local observance of the end of Ramadan as offensive, particularly on the day, September 11, when our nation and the world were paying tribute to those who died in the 9/11 terrorist attacks nine years ago," wrote Connor.

In Time Magazine, critic James Poniewozik called Connor's behavior "craven" and "depressing for the state of journalism.

"[24] In an appearance on NPR's On The Media, Connor admitted that "some of the people who complained about the lack of 9/11 coverage were really couching anti-Muslim and anti-Islamic attitudes," but refused to retract his apology, and he eventually hung up on host Bob Garfield before the segment was over.

[26] Connor finally left the newspaper at the end of 2011 under strong pressure from the board of directors and a restructuring firm that had taken over day-to-day management.

[34] Notable alumni of the paper include Thomas Haskell, known as Cap'n Haskell, who covered marine news for the Eastern Argus newspaper from 1857 to 1920 until it merged with the Portland Press and stayed with the paper until three months prior to his death in 1928;[35] May Craig, who was Washington correspondent from 1935 to 1965;[36] sportswriter Steve Buckley, who later joined the Boston Herald;[37] sportswriter Jerry Crasnick, who later worked for ESPN and is now senior advisor to the Major League Baseball Players Association;[38] Marjorie Standish, who wrote a food column for the Maine Sunday Telegram for 25 years;[39] former New York Times music critic Allan Kozinn, who was the classical music critic from 2015-2020,[40][41] and investigative journalist and book author Colin Woodard, who won a George Polk Award in 2012, was named Maine Journalist of the Year in 2015, and was a finalist for a Pulitzer Prize in 2016;[42] [43] [44] Current notable journalists include vegan food columnist Avery Yale Kamila, who is ranked by polling firm YouGov as one of The Most Popular Columnists in America,[45] sports columnist Tom Caron,[46] and retired opinion columnist Bill Nemitz, who was named Maine Journalist of the Year in 2004 and occasionally writes a column.

"[50] In 2016, Colin Woodard of the Portland Press Herald was a finalist for the 2016 Pulitzer Prize in Explanatory Reporting for his "compelling account of dramatic ecological changes occurring in the warming ocean region from Nova Scotia to Cape Cod.

"[51] In 2016, the Portland Press Herald reporters Whit Richardson and Steve Mistler received a Gerald Loeb Award for their 2015 series "Payday at the Mill" in the "Local" category.

[1] In the 1920s, under Guy P. Gannett's leadership, the newspaper adopted a more balanced editorial approach, and today the news and opinion sections of the paper are separate.

[55] Later in the 20th century, the Press Herald was regarded as having a more liberal and pro-Democratic editorial stance than the Bangor Daily News, which leaned toward conservatism and Republicans.

[56] Over its history, however, the Press Herald "has covered and endorsed candidates of various political persuasions, including independents Angus King, who was elected governor in 1994 and 1998, and Eliot Cutler, who came in second in the 2010 gubernatorial campaign.

"[1] The Press Herald endorsed conservative Republican candidates (Dean Scontras and Jason Levesque) in both of Maine's congressional districts in 2010.

[61] In 1923, Guy Gannett built the Press Herald Building to house all of the paper's operations at 390 Congress Street across from Portland City Hall.