Westport Country Playhouse To Host 'Cruel Summer: The Playhouse Playlist' This Month

WESTPORT, CT — Westport Country Playhouse will present “Cruel Summer: The Playhouse Playlist,” a back-to-school concert featuring music by contemporary pop artists, at 7 p.m. on Friday, Aug. 28.

The concert will feature songs by Taylor Swift, Ariana Grande, Olivia Dean, Sabrina Carpenter and other artists, performed by vocalists backed by a live band. Performers will be announced at a later date.

Drew Wutke is the event’s creator, producer and music director. Wutke has worked as a music director and pianist on Broadway, off-Broadway, regionally and on tour. He also serves as a resident music director and operates a private coaching studio in New York City.

At Westport Country Playhouse, Wutke previously served as music director for “From Broadway to Hollywood,” “A Night for Swifties” and “Me, Myself & Barbra.”

Tickets cost $45, $55 and $65. Ticket holders younger than 13 must have adult supervision.

Westport Country Playhouse is located at 25 Powers Court, off Route 1 in Westport. Tickets and additional information are available at westportplayhouse.org or through the box office at 203-227-4177 or 888-927-7529.

Barbara Streicker is the Playhouse’s 2026 programming and season sponsor. Moffly Media and WSHU Public Radio are media sponsors. Westport Country Playhouse is a nonprofit organization.

The Playhouse said event titles, artists, song selections, dates and times are subject to change.

— Flyer from Westport Country Playhouse