While at Hindman, Raymond Kane developed an interest in bluegrass music; he introduced his three eldest children—Raymond Winslow, Alice, and Ruth—to the genre, and the four of them began playing together.

[11] They also appeared on the CBS Morning News, the Grand Ole Opry, Hee Haw, The Johnny Cash Show, Music City Tonight, Nashville Now, Today,[12] and their own weekly program on WKYT-TV.

[23] Raymond Kane had envisioned for years a family-friendly bluegrass festival dedicated to performing family groups, and in 1978 he found a 73-acre (30 ha) farm on U.S. Route 421[31] in Bighill, Kentucky that perfectly met the needs of such a festival: "I found this farm with this marvelous hill forming a natural amphitheater.

In 1987, the entrance fee was US$10 (equivalent to $26.82 in 2023); the festival ran for three days from noon to 11 p.m.,[30] and ultimately lasted for ten years.

"[23] The McLain Family Band's music has been reviewed as being "'cheery,' 'light,' and 'wholesome'", and lacking the painful, "dark and haunted side of bluegrass".

[32] The McLain Family Band also played with symphonic orchestras, presenting pieces arranged by Phillip Rhodes, Newton Wayland,[4] and P. D. Q. Bach (the fictional alter-ego of Peter Schickele).

"[16] Rhodes also composed orchestral arrangements of original McLain Family Band songs under a commission by the Cincinnati Symphony Orchestra.

[35] One of the band's most-requested pieces is "Kentucky Wind", a song written by Raymonds K. and W. while homesick during a South American tour.

[13] In 1970, Raymond Kane began teaching the United States' first university-level courses in bluegrass and Appalachian music at Berea College.

She taught English country dance, and was an executive field director for the Wilderness Road Girl Scout Council.

[42] In 2000, Raymond Winslow was made the director of the Bluegrass and Country Music Program at East Tennessee State University.

[5] A high tenor[43] playing clawhammer banjo,[44] and fiddle, Raymond Winslow is the most well-known of the McLain family outside of the band,[2] and one of "the most well-traveled musicians in his field".

[46] After the family band stopped touring in 1989, Raymond Winslow joined Jim & Jesse and played with them for 10 years.

1952)[16] grew up playing music in New Mexico, and moved to Louisville, Kentucky to join the band Bluegrass Alliance.

Al joined the McLain Family Band after marrying Alice;[50] he plays mandolin and guitar,[30] and sings.

[50] There, as of 2017[update], Alice was a first-grade teacher, Al taught traditional instrument instruction at Berea College,[5] and the two of them played concerts and for folk and contra dancing.

[54] Prior to 2007, she married Philip Smith, and they have four children;[12] in 2011, she moved back to Berea, Kentucky to care for her mother, Betty.

[50] Nancy Ann McLain Wartman was born in 1965,[16] had joined the band by 1979,[10] and performs on double bass, mandolin, and vocals.

[36] Nancy Ann joined up with Usborne Publishing in 1994 and held the position of director within the company as of September 2016[update].

[56] He has played with the Claire Lynch Band and Dale Ann Bradley,[19] and he married his wife Jennifer a week after proposing atop the Crowne Plaza in Nashville, Tennessee.

[63] In his review of the band's 1982 performance at Carnegie Hall, Robert Palmer described the combination of traditional bluegrass and "archaic modal harmonies" as slick and modern.

"[43] The Pittsburgh Press called a McLain Family Band performance "full of open-hearted earnestness, wholesomeness and energy.

"[16] In 2013, the McLain Family Band received a Distinguished Achievement Award from the International Bluegrass Music Association.

[65] The State Department acquired a review by an NEA panel member, replying, "McLain Family Band is pleasantly amateurish, however, their enthusiasm and spirit make up for their lack of polish and on this basis he would give a 'good' rating.

[...] By every indication, McLain's 'bluegrass music' seems very welcome expression of Americana here; it helped dispel notion that Kentucky means only 'fried chicken'.

The variety of the McLain program — humorous songs blended with religious and regional numbers impressed the listeners with the richness of bluegrass music.

The musical talents and personalities particularly of young Raymond [Winslow] McLain and his sister Ruth provoked continuous applause.

The misical [sic] arrangements are simple and straight-forward but one never doubts the professionalism, the careful timing and pacing of the program.

Audiences included classical music composers, journalists, theatre personalities and, in large numbers, young students.

The McLains already have many commitments for 1976 but if they are available for a European tour the post requests a one-week program which will allow provincial city visits.High praise came from United States Ambassador to Hungary Eugene V. McAuliffe after the band played there from May 25–30, 1975.