[2] The move was initiated by CBS after its existing Boston station, WNAC-TV (channel 7) was agreed to be sold by RKO General to NBC in a deal which ultimately never materialized.

[3][4][5] Initially, WHDH-TV shared studio facilities with WHDH radio located at 6 St. James Avenue in Boston's Back Bay; but this facility was far from ideal for television and in early 1960, the station moved into a newly built studio center at 50 Morrisey Boulevard in the Dorchester section of Boston.

Almost as soon as it signed on, the Federal Communications Commission (FCC) began investigating allegations of impropriety in the granting of the television license.

Herald-Traveler Corporation fought the decision in court, but lost its battle in 1972; and Boston Broadcasters was awarded a full license.

In the months after the Herald-Traveler lost the channel 5 license, it was under court order to sign off daily at 1:00 a.m. so that WCVB-TV could test its equipment.

WHDH's newscasts were known as WHDH-TV News, a title that was used until March 18, 1972, when the station signed off for the last time and was replaced by WCVB.

An average of 56 regular-season games were televised each year, equally split between home and away matches, with all but a handful being on weekends.

One game, on February 12, 1966, a Saturday matinee from the old Madison Square Garden in New York City against the New York Rangers was carried live and in color back to Boston, using a color mobile unit owned by New York-based independent station WOR-TV (at that time co-owned with Boston station WNAC-TV; now known as Secaucus, New Jersey-licensed WWOR-TV and owned by Fox Television Stations)—which produced a videotaped broadcast of the game to air in that market that evening.

WIHS carried some regular-season Celtics' road games during the 1964–65 season, but team officials, worried about the low penetration of UHF receivers in the Boston area, arranged for WHDH to simulcast 1965 playoff games in order to reach a wider audience.

The show was extremely successful and remained on channel 5 (with Gillis still as host) until January 1996, long after WHDH had given way to WCVB.