The second collaboration between Sondheim and Lapine after Sunday in the Park with George (1984), Into the Woods debuted in San Diego at the Old Globe Theatre in 1986 and premiered on Broadway on November 5, 1987, where it won three major Tony Awards (Best Score, Best Book, and Best Actress in a Musical for Joanna Gleason), in a year dominated by The Phantom of the Opera.

She explains the curse will be lifted if she is brought four ingredients – "the cow as white as milk, the cape as red as blood, the hair as yellow as corn, and the slipper as pure as gold" – in three days' time.

All begin the journey into the woods: Jack to sell his beloved cow; Cinderella to her Mother's grave; Little Red to her Grandmother's house; and the Baker, refusing his wife's help, to find the ingredients ("Prologue").

The Witch explains Rapunzel's hair will not work as she could not have touched the ingredients, and the Mysterious Man offers corn silk instead; Milky White produces the potion.

Everyone still has wishes: the Baker and his wife face new frustrations with their infant son; newly rich Jack misses the kingdom in the sky; Cinderella is bored with life in the palace ("So Happy").

Other cast replacements included Dick Cavett as the Narrator (as of July 19, 1988, as a temporary engagement after which Aldredge returned), Edmund Lyndeck as the Mysterious Man, Patricia Ben Peterson as Cinderella, LuAnne Ponce returning as Little Red, Jeff Blumenkrantz as Jack, Marin Mazzie as Rapunzel (as of March 7, 1989), Dean Butler and Don Goodspeed as Rapunzel's Prince, Susan Gordon Clark as Florinda, Teresa Burrell as Lucinda, Adam Grupper as the steward, Cindy Robinson and Heather Shulman as Snow White, and Kay McClelland, Lauren Mitchell, Cynthia Sikes, and Mary Gordon Murray as the Baker's Wife.

[10] In 1989, from May 23 to May 25 the full original cast (with the exception of Cindy Robinson as Snow White instead of Jean Kelly) reunited for three performances to tape the show in its entirety for the Season 10 premiere episode of PBS's American Playhouse, which first aired on March 15, 1991.

The show was filmed professionally with seven cameras on the set of the Martin Beck Theatre in front of an audience, with certain elements slightly changed for the recording in order to better fit the screen, such as the lighting and minor costume differences.

Appearing were Bernadette Peters, Joanna Gleason, Chip Zien, Danielle Ferland, Ben Wright and husband and wife Robert Westenberg and Kim Crosby.

The cast included Cleo Laine as the Witch, Rex Robbins as the Narrator and Mysterious Man, Ray Gill and Mary Gordon Murray as the Baker and his wife, Kathleen Rowe McAllen as Cinderella, Chuck Wagner as the Wolf/Cinderella's Prince, Douglas Sills as Rapunzel's Prince, Robert Duncan McNeill and Charlotte Rae as Jack and his mother, Marcus Olson as the Steward, and Susan Gordon Clark reprising her role as Florinda from the Broadway production.

[16][17] The tour ran at the John F. Kennedy Center for the Performing Arts from June to July 16, 1989, with The Washington Post's reviewer writing: "his lovely score—poised between melody and dissonance—is the perfect measure of our tenuous condition.

A revival at the Royal Opera House's Linbury Studio in Covent Garden had a limited run from June 14 to 30, 2007, followed by a short stint at The Lowry theatre, Salford Quays, Manchester on 4–7 July.

The Olivier Award-winning Regent's Park Open Air Theatre production, directed by Timothy Sheader and choreographed by Liam Steel, ran for a six-week limited season from 6 August to 11 September 2010.

Whilst the book remained mostly unchanged, the subtext of the plot was dramatically altered by casting the role of the Narrator as a young school boy lost in the woods following a family argument – a device used to further illustrate the musical's themes of parenting and adolescence.

The Daily Telegraph reviewer, for example, wrote: "It is an inspired idea to stage this show in the magical, sylvan surroundings of Regent's Park, and designer Soutra Gilmour has come up with a marvellously rickety, adventure playground of a set, all ladders, stairs and elevated walkways, with Rapunzel discovered high up in a tree.

[41] For its annual fully staged musical event, the Hollywood Bowl produced a limited run of Into the Woods from July 26–28, 2019, directed and choreographed by Robert Longbottom.

[42] The cast included Skylar Astin as the Baker, Sutton Foster as the Baker's Wife, Patina Miller as the Witch, Sierra Boggess as Cinderella, Cheyenne Jackson as the Wolf/Cinderella's Prince, Chris Carmack as Rapunzel's Prince, Gaten Matarazzo as Jack, Anthony Crivello as the Mysterious Man, Edward Hibbert as the Narrator, Shanice Williams as Little Red, Hailey Kilgore as Rapunzel, Rebecca Spencer as Jack's Mother, original Broadway cast member Gregory North as Cinderella's father, and Whoopi Goldberg as the voice of the Giantess[43] The production featured Ann Hould-Ward's costumes from the Original Broadway Production.

[44] In August 2021, it was announced that Christian Borle, Sara Bareilles, Ashley Park, and Heather Headley had joined the cast as, respectively, the Baker, his wife, Cinderella, and the Witch.

cast transferred, with the additions of Brian d'Arcy James as the Baker, Patina Miller as the Witch, Phillipa Soo as Cinderella, and Joshua Henry as Rapunzel's Prince.

[53] Other new cast members included Nancy Opel as Cinderella's Stepmother, Aymee Garcia as Jack's Mother, Alysia Velez as Rapunzel, and Paul Kreppel, Diane Phelan, Alex Joseph Grayson, Felicia Curry, Delphi Borich, and Lucia Spina as understudies.

Montego Glover also began sharing the role of the Witch with Miller, and Andy Karl played a limited run as the Wolf/Cinderella's Prince from September 6–15, filling in for Creel.

The cast included Julian Bleach as the Mysterious Man, Nicola Hughes as the Witch, Rhashan Stone as the Baker, Alex Young as the Baker's Wife, Nathanael Campbell as the Wolf and Cinderella's Prince, Audrey Brisson as Cinderella, Barney Wilkinson as Jack, Gillian Bevan as Jack's Mother, Charlotte Jaconelli as Florinda, Maria Conneeley as Rapunzel, and Lauren Conroy as Little Red Ridinghood in her first professional stage debut.

In contrast to the simultaneous Broadway revival, this production was quite visual, with elaborate sets and props, its conceit being that the characters are figures in a Victorian toy theatre a young girl is playing with.

Block as the Baker and his Wife, Gavin Creel as the Wolf/Cinderella's Prince, Cole Thompson as Jack, Katy Geraghty as Little Red, David Patrick Kelly as the Narrator/Mysterious Man, Nancy Opel as Cinderella's Stepmother, Aymee Garcia as Jack's Mother (from Boston onward), Ta'Nika Gibson as Lucinda, Brooke Ishibashi as Florinda, Jim Stanek as the Steward, Alysia Velez as Rapunzel, and Kennedy Kanagawa as Milky White/puppeteer, all reprising their Broadway roles.

Other cast members included Rayanne Gonzales as Jack's Mother (in Buffalo and Washington, D.C. only), Josh Breckenridge as Cinderella's father/puppeteer, and Paul Kreppel, Sam Simahk, Erica Durham, Ellie Fishman, Marya Grandy, Ximone Rose, and Eddie Lopez as understudies.

[108] A 25th-anniversary co-production between Baltimore's Center Stage and Westport Country Playhouse directed by Mark Lamos was notable for casting original Little Red Ridinghood, Danielle Ferland, as the Baker's Wife.

The cast included Erik Liberman as the baker, Lauren Kennedy as the Witch, Jeffry Denman as the Narrator, Nik Walker as the Wolf/Cinderella's Prince, Dana Steingold as Little Red Ridinghood, Justin Scott Brown as Jack, Jenny Latimer as Cinderella, Cheryl Stern as Jack's Mother, Robert Lenzi as Rapunzel's Prince/Cinderella's father, Alma Cuervo as Cinderella's Stepmother/Granny/Giantess, Britney Coleman as Rapunzel/Cinderella's Mother, Nikka Lanzarone as Florinda, Eleni Delopoulos as Lucinda, and Jeremy Lawrence as the Mysterious Man.

[122] The Israeli premiere of the musical, אל תוך היער (El Toch Ha-ya-ar), opened in Tel Aviv in August 2016 for a limited run produced by The Tramp Productions and Stuff Like That,[123] starring Roi Dolev as the Witch, the second male actor to do so.

It starred Mykal Kilgore as the Witch, Mara Davi as the Baker's Wife, Jonathan Raviv as the Baker, Pepe Nufrio as Rapunzel's Prince, Sarah Dacey Charles as Cinderella's Stepmother/Granny/Cinderella's Mother, Dorcas Leung as Little Red Ridinghood, Amanda Robles as Cinderella, Thom Sesma as the Narrator/Mysterious Man, Kevin Toniazzo-Naughton as the Wolf/Cinderella's Prince, Clay Singer as Jack, Zoë Aarts as Lucinda, Megan Orticelli as Florinda, and Leslie Becker as the Giantess/Jack's Mother.

[128] A 2022 production staged at Arkansas Repertory Theatre featured the pre-recorded voice of former Secretary of State and one-time Presidential nominee Hillary Clinton as the Giantess.