The group started as a San Francisco Bay Area nightclub act with an original lineup of Dave Guard, Bob Shane, and Nick Reynolds.

At Menlo, Shane became friends with Nick Reynolds, a native San Diegan with an extensive knowledge of folk and calypso songs—in part from his guitar-playing father, a career officer in the U.S.

At one engagement at Redwood City's Cracked Pot beer garden, they met a young San Francisco publicist named Frank Werber, who had heard of them from a local entertainment reporter.

[17] Werber imposed a stern training regimen on Guard, Shane, and Reynolds, rehearsing them for six to eight hours a day for several months, sending them to prominent San Francisco vocal coach Judy Davis to help them learn to preserve their voices, and working on the group's carefully prepared but apparently spontaneous banter between songs.

At the same time, the group was developing a varied and eclectic repertoire of calypso, folk, and foreign language songs, suggested by all three of the musicians though usually arranged by Guard[12] with some harmonies created by Reynolds.

[18] The first major break for the Kingston Trio came in late June 1957 when comedian Phyllis Diller canceled a week-long engagement at The Purple Onion club in San Francisco.

[21] Werber built upon this initial success, booking a national club tour in early 1958 for the Trio that included engagements at such prominent night spots as Mister Kelly's in Chicago, the Village Vanguard in New York, Storyville in Boston, and finally a return to San Francisco and its showcase nightclub, the hungry i, in June of that year.

[22] Through Jimmy Saphier, agent for Bob Hope who had seen and liked the group at The Purple Onion, Werber contacted Capitol Records, which dispatched prominent producer Voyle Gilmore to San Francisco to evaluate the Trio's commercial potential.

[23] The song selections on the first album reflected the repertoire that the musicians had been working on for two years—re-imagined traditional songs inspired by The Weavers like "Santy Anno" and "Bay of Mexico", calypso-flavored tunes such as "Banua" and "Sloop John B" that were reminiscent of the popular Harry Belafonte recordings of the time, and a mix of both foreign language and contemporary songwriter numbers, including Terry Gilkyson's "Fast Freight" and "Scotch and Soda", whose authorship remains unknown as of 2023.

[24] The album sold moderately well—including on-site sales at the hungry i during the Kingston Trio's engagement there through the summer—but it was DJs Paul Colburn and Bill Terry at station KLUB in Salt Lake City whose enthusiasm for a single cut on the record spurred the next development in the group's history.

Colburn began playing "Tom Dooley" extensively on his show, prompting a rush of album sales in the Salt Lake area by fans who wanted to listen to the song, as yet unavailable as a single record.

[42] Following a meeting with attorneys on May 10, 1961, intended to resolve the dispute,[44] Dave Guard resigned from the Kingston Trio, though pledging to fulfill group commitments through November of that year.

The British Invasion spearheaded by The Beatles, who were signed by EMI/Capitol just as the Trio's seven-year contract was running out, depressed sales of acoustic folk albums significantly, and Capitol did not make a serious effort to re-sign the group.

[50] By 1966, Reynolds had grown weary of touring and Stewart wanted to strike out on his own as a singer-songwriter, so the three musicians and Werber developed an exit strategy of playing as many dates as possible for a year with an endpoint determined to be a final two-week engagement at the hungry i in June 1967.

[52] Following the hungry i engagement, Reynolds moved to Port Orford, Oregon and pursued interests in ranching, business, and race cars for the next twenty years.

[53] Stewart commenced a long and distinguished career as a singer-songwriter, composing hit songs like "Daydream Believer" for The Monkees and "Runaway Train" for Rosanne Cash.

He recorded more than 40 albums of his own, most notably the landmark California Bloodlines, and found chart success in the top forty with "Midnight Wind", "Lost Her in the Sun", and "Gold", the latter reaching number 5 in 1979.

The nine years of this configuration was to that point the longest period of time that any three musicians had worked together as the Kingston Trio, and the group released two albums of largely original material.

[60] It was during this period as well that PBS producers JoAnne Young and Paul Surratt approached Shane and the other principals of the original group with the idea of arranging a reunion concert that would be taped and used as a fundraiser for the network.

Agreement was reached, and on November 7, 1981, Dave Guard, Nick Reynolds, and John Stewart joined the Shane-Gambill-Grove Trio and guest performers Mary Travers of Peter, Paul and Mary, Tom Smothers of the Smothers Brothers, and Lindsey Buckingham of Fleetwood Mac at the Magic Mountain amusement park north of Los Angeles for a show billed as "The Kingston Trio and Friends Reunion.

[4] Peter Dreier of Occidental College observed that "Purists often derided the Kingston Trio for watering down folk songs in order to make them commercially popular and for remaining on the political sidelines during the protest movements of the 1960s.

"[77] Frank Proffitt, the Appalachian musician whose version of "Tom Dooley" the Trio rearranged, watched their performance of his song on a television show and wrote in reaction, "They clowned and hipswung.

In an obituary for Nick Reynolds (d. October 1, 2008), Spencer Leigh wrote in Britain's Independent on Sunday: Looking at their repertoire now, it is apparent that the Kingston Trio was far more adventurous than is generally supposed.

They introduced "It Was A Very Good Year" in 1961, later a standard for Frank Sinatra, and they were one of the first to spot the potential of English language versions of Jacques Brel's songs by recording "Seasons in the Sun" in 1963.

[86] Further, Peter Dreier points out that "the group deserves credit for helping to launch the folk boom that brought recognition to older folkies and radicals like Woody Guthrie and Pete Seeger, and for paving the way for newcomers like Joan Baez, Bob Dylan and Phil Ochs, who were well known for their progressive political views and topical songs.

"[88] In February 1982, Chicago Tribune writer Eric Zorn praised the Kingston Trio's impact on the popular music industry, claiming that "for almost five years, they overshadowed all other pop groups in America."

"[89] Jac Holzman, co-founder of the originally folk-based Elektra Records, remarked that his formerly struggling company's new-found prosperity in the late 1950s resulted from "The Kingston Trio which has the ability to capture the interest of a large number of people who have never been conscious of folk music before.

In her memoir And A Voice To Sing With, singer and activist Joan Baez recalled that "Traveling across the country with my mother and sisters, we heard the commercial songs of the budding folk boom for the first time, the Kingston Trio's 'Tom Dooley' and 'Scotch and Soda.'

"[92] Among the many other artists who cite the Kingston Trio as a formative influence in their musical careers are comedian, actor, and banjo player Steve Martin,[93][94] Lindsey Buckingham of Fleetwood Mac,[95] singer-songwriter Paul Simon,[96] Timothy B. Schmit[97][98] of The Eagles, pioneering folk-rock artist Gram Parsons,[99] Stephen Stills and David Crosby of Crosby, Stills, and Nash,[100] The Beach Boys' Al Jardine,[101] Big Brother and the Holding Company founding member Peter Albin,[102] Denny Doherty of The Mamas and the Papas,[103] banjo master Tony Trischka,[104] pop groups ABBA[105] and The Bee Gees,[106] Jefferson Airplane founding members Marty Balin[107] and Paul Kantner,[108] Buffalo Springfield founding member Richie Furay,[109] Byrds co-founder Gene Clark,[110] roots musician and master mandolin player David Grisman,[111] singer-songwriters Tom Paxton,[85]Harry Chapin,[112] Jimmy Buffett,[113] Tim Buckley,[114] Steve Goodman,[115] Steve Gillette,[116] Michael Smith[117] (composer of "The Dutchman"), and Shawn Colvin,[118] folk-rock group We Five co-founder Jerry Burgan,[119] folk and rock musician Jerry Yester,[120] rock photographer and Modern Folk Quartet musician Henry Diltz,[121] and progressive jazz vocal group Manhattan Transfer.

[122][123] The classic stage look of The Beach Boys from the early to late 1960s, blue and white striped button-down shirts with either black or grey pants, was inspired by the Kingston Trio.