Woodstock Christmas Shows 2026

Audiences watch comedy duo Rick Compton and Betsy Bennett portray 18 lively characters celebrating the season at Pelican Roost retirement community. The musical comedy follows the residents as they sing, dance, spin the dreidel, and organize a holiday golf cart...

Attendees experience an evening of virtuosic instrumentals, holiday favorites, and breathtaking guitar arrangements. The concert features performances by acclaimed guitarists Christie Lenée, Gareth Pearson, and Muriel Anderson, showcasing dynamic fingerstyle playing, energetic acoustic sets, and harp-guitar artistry. The event also...

Visitors enjoy a relaxed, welcoming cinema screening of the 1954 Technicolor holiday musical starring Bing Crosby and Danny Kaye. The storyline follows a song-and-dance duo teaming up with a sister act in Vermont to help save a former general's struggling...

Sibling trio Bekah, Caleb, and Joshua Liechty deliver a heartfelt holiday performance blending folk, pop, and rich three-part harmonies. The concert features fresh interpretations of beloved Christmas classics alongside original songs, including their hit 'One More Christmas.'

Audiences experience a fresh take on the classic holiday ballet presented by M3 Dance Company. The performance brings together an ensemble of students, pre-professionals, and professional artists from ballet and contemporary companies. The staging features beautifully crafted costumes and unique...

Guests follow Clara's journey beginning at her family's Christmas Eve party, where an evening of dancing and celebration leads to a dream with her precious Nutcracker doll. Audiences watch Clara and Drosselmeyer battle a life-size Mouse Queen, slide alongside snowmen...

Audiences watch a festive jukebox musical following Jack, an ambitious New York advertising executive who doesn't believe in magic, after he is unexpectedly chosen by the Bells of SinterKlaas to succeed Santa Claus. The production brings together youth and adult...

Guests experience the story of Clara’s magical adventure through short dance performances by the Barrington Dance Ensemble alongside interactive dancing and photo opportunities with characters. Vintage holiday treats from Ambrosia Euro-American Pâtisserie are served during the gathering. Attendees also receive...

Audiences can watch a live holiday performance of Boy Band Review: Boy Band Christmas at the Hemmens Cultural Center. The stage presentation has a running time of 90 minutes.

Operatic baritone and Eurovision pop artist Vasil Garvanliev takes the stage for a live holiday concert at Barrington’s White House. The performance highlights his vocal versatility, blending classical opera technique with pop music.

Emmy nominee Angela Ingersoll captures the voices of a dozen divas in a festive holiday romp presented by Artists Lounge Live. The concert features vocal performances channeling stars like Judy Garland, Julie Andrews, and Janis Joplin. Audiences will hear seasonal...

Attendees can enjoy an evening of festive winter songs. The musical performance is presented by the Palatine Park District's Allegro Community Choir under the direction of Kevin Kelly. The concert is open to guests of all ages.

Join the University of Saint Mary of the Lake for their annual Sounds of the Season Christmas Concert. This cherished tradition fills the historic Main Chapel with the enchanting sounds of Christmas, performed by the seminary's talented seminarians. Experience a...