Tiring of life in New York City, where he had worked as a reporter at the New York Times, and wanting to raise his six-year-old son Benjie in a different environment, 44-year-old widower Bob Major moves with Benjie to Phippsboro, a small, sleepy rural town in New Hampshire with a population of about 3,000, where he purchases the town's only newspaper, the weekly Phippsboro Bulletin, from its longtime owner and editor, Ichabod Adams.

[1][2][3][4][5][6] Bob's big-city attitudes and ideas often clash with the small-town ways of the natives of Phippsboro, who are stereotypical rural New Englanders – taciturn, frugal, suspicious of strangers like him, and set in their ways;[1][4][7] he is prone to writing inflammatory editorials in the Bulletin calling for progress in the town to bring it into the mid-20th century and raising the ire of the townspeople, who tend to oppose change.

[1][4][7] Ichabod – who is in his 60s,[7] owns most of the town[1][2] and serves it in many capacities, including as its mayor for the past 28 years,[4][7] its school superintendent, and its traffic commissioner[8] — remains involved in the operation of the newspaper.

[1][3] Bob complains about how hard it is to keep a secret in Phippsboro, where residents – Martin and Colby in particular – listen in on the town's party line to eavesdrop on other people's business.

[4] In "Adam's Apples," a character named Terrence "Terry" Major,[4][10] portrayed by Fred Beir,[4][10] gives up life as an advertising executive in New York City and retires to Phippsboro to become a gentleman farmer, and he rents property from Ichabod.

[10] Despite the pilot's failure, Chandler felt strongly about getting a regular series on the air based on the Ichabod Adams and "Mr. Major" characters.

[10] He took the initiative in forming a partnership with co-creators Joe Connelly and Bob Mosher and with comedian Jack Benny, whose production company put up much of the funding for the regular series Ichabod and Me.

[12] Pete Rugolo and His Orchestra[13] performed the opening and closing theme of Ichabod and Me, which was an updated, uptempo arrangement of the traditional folk song "The Girl I Left Behind Me"[11] — a fife-and-drum-corps classic[11] which connoted the American Revolutionary War era in New England.

Variety panned Ichabod and Me in its October 4, 1961, issue as "just another run-of-the-mill situation comedy, typically innocuous in its content and wholly bland in its approach...there were no surprises and few laughs on its first outing.

Rod Serling's guest appearance drew some attention to the series in March 1962, but did not improve its ratings, and by April 1962 Robert Sterling was acknowledging in interviews that the show was unlikely to return for a second season.

Eastern on ABC, while on NBC Ichabod and Me aired opposite the second half of The Dick Powell Show, an anthology series.