5 regional productions worth the trip this May

To quote the late, great Peter Allen, the theme of this month’s regional roundup is “everything old is new again.” Both vintage and future classics are at the forefront, exploring age-old yet forever relevant themes of family (and what happens when they get too close), democracy (forever an active verb rather than a fleeting concept), and addiction (because our smartphones really are that powerful). Add in an exciting world premiere about an advice columnist facing a bitter end (or not?), and May proves to be a fruitful month for theatergoers everywhere.

‘Octet’ at Raven Theatre, Chicago

Dave Malloy's 'Octet' runs from April 30-June 7.

Lin-Manuel Miranda recently announced he’ll be directing the film adaptation of Octet, an exploration of a screen-addiction support group through a capella music. The star-studded cast includes Amanda Seyfried, Sheryl Lee Ralph, and Rachel Zegler (headed to Broadway next spring in Evita). Here’s your chance to see it live at Raven Theatre on Chicago’s North Side, where the story is set.

Performances through June 7, 2026

‘Louisa May Alcott’s Little Women’ at Guthrie Theater, Minneapolis

The four March sisters are joined by Louisa May Alcott in Guthrie Theater's production of Little Women. — Guthrie Theater’s production of “Little Women.” Photo provided.

Guthrie Theater’s new production brings a fresh twist to the coming-of-age classic, putting author Louisa May Alcott at the forefront. Directed by Jackson Gay, Louisa May Alcott’s Little Women features a script by playwright Lauren Gunderson. It also leverages the power of regional theater collaboration. City Theatre Company, Northlight Theatre, People’s Light, and TheatreWorks Silicon Valley co-commissioned the work. This new adaptation explores the complexities of the four March sisters, their dreams and loves, and their evolution alongside post-Civil War society.

Performances through June 21, 2026

‘Oedipus el Rey’ at The Huntington, Boston

Javier David, Juan Arturo, Victor Almanzar, Gabe Martinez (top row) Jaime Jos Hernandez, Melisa Pereyra (bottom row) star in Oedipus el Rey. — Javier David, Juan Arturo, Victor Almanzar, Gabe Martinez (top row), Jaime Jos Hernandez, and Melisa Pereyra (bottom row) star in Oedipus el Rey. Photo by Nile Hawver

This is not the Oedipus you read in high school, or the recent Broadway revival, which turned the Greek tragedy into a political thriller. Fourteen years and countless shows after its 2012 Chicago premiere, Luis Alfaro’s searing Chicano reimagining of the Sophocles play lives on in my mind and heart. Set in and around a Los Angeles prison and now playing at The Huntington in Boston, Oedipus el Rey takes an ancient story of dark fate to soaring heights and devastating lows.

Performances through June 7, 2026

‘Dear Alien’ at Alley Theatre, Houston

Promo image for Dear Alien — Dear Alien runs May 8 – 31 at Alley Theatre

Supported by the Edgerton Foundation New Play Award—the same award that helped develop Hamilton, Dear Evan Hansen, and Next to Normal—the world premiere of Dear Alien is an exciting new existential comedy by Liz Duffy Adams. As an advice columnist faces financial ruin, she must meet one last deadline, but of course, nothing is ever that straightforward. Support the creation of brand-new art this month at Houston’s Alley Theatre, which won the 1996 Regional Theatre Tony Award after debuting the world premiere of Jekyll & Hyde.

Performances through May 31, 2026

‘1776’ at Walnut Street Theatre, Philadelphia

From the first shout of “Sit down, John!”, 1776 became an instant classic, a musical theater take on the Founding Fathers. Celebrate the 250th anniversary of the signing of the Declaration of Independence—and the complexities behind our country’s history from literal Day One—at Philadelphia’s Walnut Street Theatre.

Performances through May 31, 2026