[7] The festival has roots in the earliest days of the University of Colorado at Boulder, when senior classes performed commencement plays under a grove of cottonwood trees planted in the 1870s on the east lawn of the first building on campus, Old Main.

The tradition was interrupted by World War I and resumed in 1919 by George F. Reynolds, an Elizabethan theater scholar and professor of English Literature.

Because the University Theatre was occupied by the Department of the Navy due to the war effort, Sandoe, also influential in developing the Oregon Shakespeare Festival, decided to stage Romeo and Juliet in the outdoor theater.

Crouch directed seven plays over the next 10 years and founded the Colorado Shakespeare Festival, which premiered on Aug. 2, 1958, and featured three productions: Julius Caesar, Hamlet, and The Taming of the Shrew.

Yang (1978-1981; 1986–89), Dick Devin (1990–94; 1997–2004), Jim Symons (1995), Philip Sneed (2007-2012; now executive director at the Arvada Center for the Arts and Humanities) and Timothy Orr (2013–present).

[12] Under Yang, the festival began hiring professional designers, technicians and directors with national reputations, including Robert Benedetti, Audrey Stanley and Tom Markus.

That same year, the Festival received the Colorado Governor's Award for Excellence in the Arts and the Denver Drama Critic's Circle Award for “Best Season for a Theatre Company.”[12] Dick Devin, who started working at the CSF as a lighting designer in 1981, and done design work in Hong Kong, Tokyo and Cairo, was selected as the festival's producing artistic director nine years later.

[15] Under Devin in the 1990s and 2000s, CSF bumped the number of annual summer productions from three to four, with occasional forays into non-Shakespeare or related material, such as Tom Stoppard's Rosencrantz and Guildenstern Are Dead in 1995 and Molière's The Miser in 1996.

[15] With the arrival of Philip Sneed in 2006,[17] CSF began producing six plays each year, including non-Shakespeare works such as Woody Guthrie’s American Song (2008) and To Kill a Mockingbird (2009).

To Kill a Mockingbird was widely praised by critics and earned a prestigious Ovation Award from The Denver Post for its director, Jane Page.

[18] Sneed was a CU-Boulder graduate and former CSF actor who came to the festival after serving as director of the Foothill Theatre Company in Nevada City, California.

In 2011, CSF hosted Gorky director Efim Zyenyatsky and Russian actors for a bi-lingual production of Nikolai Gogol's The Inspector General.

[23] The festival had sought to halt the mounting losses by cutting rehearsal time, staff and payroll, and reducing the number of outdoor performances, even while continuing to emphasize innovation.

[24] In addition, in November 2012, CSF's box-office, marketing and communications functions were integrated, along with those of the CU-Boulder Department of Theatre and Dance, into CU Presents, a program of the College of Music that provides those services for other ticketed events on campus, including the Artist Series, Takács Quartet and Holiday Festival.

[26] The 2013 season — A Midsummer Night’s Dream, Macbeth, The Complete Works of William Shakespeare, Abridged, Richard II and Women of Will: The Overview — saw a 17-percent increase in ticket revenue, which allowed the festival to pay off loans for capital improvements to the Rippon theater and make a voluntary contribution to the college in an effort to repay debt underwriting.

[34] As interim director, Orr oversaw planning for the upcoming season, which included The Tempest, The Merry Wives of Windsor, I Hate Hamlet, Paul Rudnick's comedy about a young actor haunted by the ghost of Shakespearean actor John Barrymore, Henry IV, Part 1 and two “original practices” performances of Henry IV, Part 2.

[37] While researching I Hate Hamlet, CU-Boulder theater graduate student Roxxy Duda stumbled upon a large, all-but-forgotten archive of Barrymore materials — letters, photographs, personal items including the contents of his wallet at death, and more.

The actor had no association with the university, but had willed the materials to his friend, theater critic Gene Fowler, a Denver native who wrote a biography of Barrymore, Goodnight, Sweet Prince.

1993 The Merry Wives of Windsor, The Tempest, King Lear, Pericles1994 Macbeth, Antony and Cleopatra, Twelfth Night, The Two Gentlemen of Verona 1995 Hamlet, Coriolanus, As You Like It, Tom Stoppard's Rosencrantz and Guildenstern Are Dead 1996 A Midsummer Night's Dream, The Merchant of Venice, Othello, Molière's The Miser 1997 Troilus and Cressida, Romeo and Juliet, Much Ado About Nothing, Molière's The Would-Be Gentleman 1998* The Taming of the Shrew, Measure for Measure, Love's Labour's Lost, Richard II 1999* Henry IV Part 1, Henry IV Part 2, The Comedy of Errors, The Merry Wives of Windsor 2000 Twelfth Night , Julius Caesar, Henry V, The Tempest 2001* King Lear, The Two Gentlemen of Verona, As You Like It, Queen Margaret 2002* A Midsummer Night's Dream, Macbeth, Shakespeare in Briefs, Richard III 2003* Hamlet, The Taming of the Shrew, Much Ado About Nothing, Cymbeline 2004 The Comedy of Errors, Antony and Cleopatra, Romeo and Juliet 2005* The Winter's Tale, Twelfth Night, Othello 2006* The Tempest, As You Like It, The Merchant of Venice, Unexpected Shakespeare 2007* A Midsummer Night's Dream, Julius Caesar, All's Well That Ends Well, Carlo Goldoni's The Servant of Two Masters, Around the World in 80 Days

2008* Macbeth, The Three Musketeers, Henry VIII, Love's Labour's Lost, Peter Glazer's Woody Guthrie's American Song2009 Hamlet, Much Ado About Nothing, To Kill a Mockingbird, The Two Gentlemen of Verona, Adam LongDaniel Singer and Jess Winfield's The Complete Works of William Shakespeare (Abridged) 2010 King Lear, The Taming of the Shrew, Measure for Measure, Harvey Schmidt and Tom Jones's The Fantasticks, Thornton Wilder's Our Town 2011 Romeo and Juliet, The Comedy of Errors, The Little Prince, Gogol's The Government Inspector 2012 Twelfth Night, Treasure Island, Richard III, Michael Frayn's Noises Off, Tina Packer's Women of Will 2013 A Midsummer Night's Dream, Macbeth, The Complete Works of William Shakespeare (Abridged), Richard II, Women of Will: The Overview 2014 The Tempest, The Merry Wives of Windsor, Paul Rudnick's I Hate Hamlet, Henry IV Part 1, Henry IV Part 2

2015 Much Ado About Nothing, Othello, David Davalos's Wittenberg, Henry V, Henry VI Part 1 2016 The Comedy of Errors, Bill Cain's Equivocation, Troilus and Cressida, Cymbeline, Henry VI Part 2 2017 The Taming of the Shrew, Hamlet, Julius Caesar, Tom Stoppard's Rosencrantz and Guildenstern Are Dead, Henry VI Part 3 2018 Love's Labour's Lost, Richard III, Edmond Rostand's Cyrano de Bergerac, George S. Kaufmman and Moss Hart's You Can't Take It With You, Edward III 2019 Twelfth Night, As You Like It, Romeo & Juliet, Mike Bartlett's King Charles III, King John 2020 Season Postponed 2021 Season Resumed - A Midsummer Night's Dream, Pericles, Mary Zimmerman's The Odyssey: A Play 2022 The Two Gentleman of Verona, All's Well That Ends Well, Lauren Gunderson's The Book of Will, Coriolanus, Ben Jonson's The Alchemist 2023 Much Ado About Nothing, The Winter's Tale, King Lear, Richard Bean's One Man, Two Guvnors, The Comedy of Errors 2024 Arden of Faversham, Macbeth, The Merry Wives of Windsor One bright spot for CSF during its financial difficulties was the creation of a three-pronged education program.

The organization provides educational support to the Colorado Shakespeare Festival through free garden tours, public presentations and research.