Roald Dahl’s beloved story comes to life on the big screen when Willy Wonka and the Chocolate Factory returns to the Westport Country Playhouse for a special cinematic presentation on August 6, 2025, at 6:00 pm. This classic 1971 musical film stars Gene Wilder as the enigmatic candy maker Willy Wonka and follows young Charlie ... Read more
Ana Gasteyer, acclaimed actress, comedian, and singer, will take the stage at the Westport Country Playhouse on August 8, 2025, at 8:00 pm for an evening of unforgettable entertainment. Best known for her iconic characters and celebrity impressions during her six-year run on Saturday Night Live, Gasteyer has built a remarkable career that spans television, ... Read more
The Wood Brothers will bring their signature blend of American roots music, insightful storytelling, and genre-defying creativity to Levitt Pavilion in Westport on Sunday, August 10, 2025, with a performance beginning at 6:00 pm. Celebrated for their heartfelt songwriting and dynamic live performances, The Wood Brothers have cultivated a loyal following over nearly two decades. ... Read more
Broadway sensation Linedy Genao takes the stage with Songs From My Sala, a musical journey inspired by the joy, harmony, and healing that have shaped her life and career. Performing at the Westport Country Playhouse on August 12 at 7:00 pm, Genao invites audiences into the warmth of her "sala"—a living room of song—where personal ... Read more
Westport’s own Suzanne Sheridan will perform a free concert at the Levitt Pavilion on August 12, 2025, at 7:00 pm, with doors opening at 6:00 pm. Accompanied by Bob Cooper on keyboards, Jake Habegger on drums, and Tim DeHuff on lead guitar, Sheridan brings a dynamic and heartfelt tribute to some of music’s most iconic ... Read more
Families are invited to a joyful, all-ages concert experience with Miss Tutti & The Fruity Band at the Levitt Pavilion in Westport on August 13, 2025, at 7:00 pm. Part of the venue’s beloved Children’s Series, this lively show offers an inclusive musical celebration for kids and grownups alike. Miss Tutti & The Fruity Band ... Read more
Celebrate the spirit of summer with Summer Jam, an uplifting night of live music, community connection, and charitable support at the Westport Country Playhouse. Taking place on Friday, August 15, 2025, at 7:00 pm, this special event features Grammy Award-winning legend José Feliciano and a lineup of talented friends. Hosted by the Church of the ... Read more
The Westport Country Playhouse will present a special screening of the 1973 classic caper film The Sting in celebration of Robert Redford’s birthday. Set in 1936 Chicago, the story follows small-time grifter Johnny Hooker (Robert Redford) who teams up with seasoned con artist Henry Gondorff (Paul Newman) to avenge the murder of Hooker’s partner by ... Read more
The Dirty Sock Funtime Band will return to the Levitt Pavilion’s Epstein Stage on Tuesday, August 19, 2025, for a lively Children’s Series finale and back-to-school celebration. Known for their wild mix of musical comedy, puppetry, singalongs, and kid-friendly adventures, the band features rock ’n’ roll best friends Mike and Stephen, their band The Dirty ... Read more
Singer, songwriter, musician, artist, and best-selling author Josh Ritter will perform with The Royal City Band at the Levitt Pavilion in Westport. Known for his thought-provoking lyrics and melodic storytelling, Ritter has released eleven studio albums, including the critically acclaimed Fever Breaks. In addition to his musical career, he is a national best-selling author of ... Read more
