November 26, 1920
Stacy Brewer publishes the first issue of The Pilot in Vass. It was said to be "devoted to the upbuilding of Vass and its surrounding country." The newspaper was housed in a building constructed by Mr. A. Cameron. It stands in Vass today.

September 7, 1928
Stacy Brewer sells the paper. "The Pilot takes great pleasure in announcing that Nelson C. Hyde of Southern Pines, formerly editor of the Syracuse (N.Y.) Herald and for several years Washington correspondent of a group of newspapers in New York State has become affiliated with this paper." Hyde's name appears as publisher for the first time Sept. 14, 1928.

October 26, 1928
The Pilot opens a branch office in the Patch Building in Southern Pines for its editorial and advertising staff. Similar offices were to be opened in Pinehurst and Aberdeen.

May 3, 1929
The Pilot publishes in Aberdeen for the first time. The paper moves there at the urging of Murdoch Johnson.

May 7, 1929
The Pilot masthead changes for the first time. The new one features a pilot and wheel which has the compass points and a map of Moore County.

1931
The average weekly net paid circulation of the paper is 1,450 copies. The price is still $2.00 per year, 5 cents a copy.

May 12, 1932
The Pilot produces an "extra" when the body of the Lindbergh baby is discovered.

July 21, 1933
The Pilot buys the plant and equipment of the Sandhill Citizen and maintains offices in both Southern Pines and Aberdeen.

Late 1933
The Pilot moves to East Broad Street.

April 1941
The Pilot moves its offices from East Broad Street to W. Pennsylvania Avenue, its fifth home since its 1920 beginning in Vass.

May 23, 1941
Nelson Hyde sells his interest in The Pilot to his friend, James Boyd, a long time resident of Southern Pines.

July 18, 1941
Nelson Hyde resigns as editor and Carl Thompson is named as the new editor.

August 15, 1941
Front page nameplate is altered, still featuring a pilot and wheel, but with a different map in the center.

December 19, 1941
The Pilot dons a new nameplate, the one with which most of us are familiar. It isdrawn by Ruth Doris Swett, a local artist, and the daughter of Dr. and Mrs. William P. Swett. The Southern Pines native executes the original drawing of the pine needles, compass and map of Moore County.

May 1944
Pilot owner and publisher James Boyd dies in Princeton, New Jersey, while at a speaking engagement. His wife, Katharine Lamont Boyd, takes over as publisher and editor.

1950
Subscriptions are $3.00, single copy sales 10 cents each.

1960
Subscriptions are $4.00, single copy sales still 10 cents each.

October 1968
Katharine Boyd sells The Pilot to Sam and Marjorie Ragan.

1970
An addition is made to the back of the building of West Pennsylvania Avenue to accommodate the offset press.

October 28, 1970
The first press run is made on the Newsking offset press.

1979
Another addition is needed to house the growing staff.

September 25, 1985
The Pilot, celebrating its 65th year of publication, converts to a six column format.

January 6, 1986
The Pilot becomes a semi-weekly paper, publishing on Monday and Thursday. At this time, the single copy price is 25 cents and the subscription price $14.00 per year.

July 1, 1996
An ownership group made up of Frank Daniels Jr., Frank Daniels III, David Woronoff, Jack Andrews and Lee Dirks -- all previously associated with the News & Observer of Raleigh -- acquire The Pilot.

March 13, 1998
Renovations begin at The Pilot's Pennsylvania Avenue location.

June 1, 1998
The new Goss Community press goes on line. The Pilot publishes four color photos for the first time.

July 23, 1998
The Pilot launches www.thepilot.com

1999
The Pilot begins The Moore County Telephone Directory, publishing white- and yellow-page listings for Moore County.

January 28, 1999
The Pilot moves back into its newly renovated offices on Pennsylvania Avenue. Cost of the expansion and renovation: $2.3 million, including $1.1 million in construction; $1 million for the new press; $180,000 for an inserting machine and $20,000 for a new forklift, which was needed to stack the rolls of paper on end.

June 14 - 21, 1999
The Pilot produces daily editions for the U.S. Open

September 1999
The Pilot implements a comprehensive typographical redesign of the newspaper.

October 1999
The Pilot begins publishing three days per week -- Monday, Wednesday and Friday.

May 2000
The Pilot launches a re-designed web site.

2001
The Pilot launches the Lee County Telephone Directory, publishing white- and yellow-page listings for Lee County.

June 2001
The Pilot produces daily editions for the U.S. Women's Open

March 9, 2003
The Pilot changes publication days to Sunday, Wednesday and Friday.

2002
The Pilot wins "Best in the Nation" Non-Daily Newspaper Competition award from The Inland Press Association.

April 2005
The Pilot acquires Whistle Stop Press.

2005
New York Times best-selling author Jim Dodson joins The Pilot as a Sunday essayist.

June 13 - 20, 2006
The Pilot produces daily editions for the U.S. Open.

July 2, 2006
Frank Daniels Jr., Frank Daniels III, David Woronoff, Jack Andrews and Lee Dirks mark 10 years of ownership of The Pilot.

July 2, 2006
The Pilot lauches a re-designed web site that includes features such as podcasts, a local online real estate guide, a new online classified placement system and online subscriber tools for vacation starts/stops and new subscriptions.

June 2007
The Pilot produces daily editions for the U.S. Women's Open

2007
The Pilot acquires PineStraw Magazine, and installs founder Andie Rose as creative director and Dodson as editor. The magazine begins publishing in a traditional glossy style a year later.

October 2010
The Pilot acquires The Country Bookshop at 140 NW Broad St. from owner Bobbie Bicket, who had owned the store since 2006.

2010
The Pilot lauches a re-designed web site that includes blogging tools, multimedia tools and the ability for users to submit content.

July 2011
The Pilot sells its printing press to a paper in Guatemala after it contracts with The News & Observer of Raleigh to print the paper.

July 2011
The Pilot launches O.Henry Magazine, a bi-monthly publication for Greensboro. The magazine is styled after the successful PineStraw.