After six seasons as Artistic Director through 2005, Ms. Woodward became Artistic Director Emeritus and remained as a Trustee, with special interest in the Playhouse education program. Ms. Woodward engendered, and enacted her vision of the Playhouse: a Connecticut treasure, and a national resource for the highest caliber theatre that rivals the best of Broadway and off-Broadway, with open doors to all in our community.

On January 1, 2006, Tazewell Thompson became the fourth artistic director in the Playhouse's long history. In his first season he directed On The Verge in a co-production with Arena Stage; the world premiere of the musical revue Jam & Spice: The Music of Kurt Weill; his own multi-award-winning play Constant Star ; and his song-filled adaptation of A Christmas Carol.

Later in 2006, Jodi Schoenbrun Carter was named managing director. She was general manager for several of off-Broadway's most-acclaimed shows, and worked with the award-winning Signature Theatre Company as general manager and transition and capital projects director.

On January 1, 2008 Joanne Woodward and Anne Keefe returned as co-artistic directors at the Playhouse. On Febraury 4, 2008, Ms. Woodward and Ms. Keefe reignited the season for Westport Country Playhouse including Oscar winner Paul Newman at the helm of Of Mice and Men. Now operating year-round, the Playhouse is an artistic beacon, annually staging eight theatrical productions, two reading series, a vibrant education program, expanded family programming, and the sold out Play Club series.

The reborn Westport Country Playhouse: a Connecticut cultural landmark, taking its place as one of America's finest professional theatres.