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Celebrate Bennington Area Arts with Four Chimneys Inn

Bennington and the surrounding area is rich with live theatre, arts, and culture. Our romantic Inn is located in the heart of these theaters, festivals, and galleries!  Book your stay at Four Chimneys Inn today and experience the fine arts of Bennington, Vermont.


Celebrating its 45th birthday, Oldcastle Theatre Company has been a favorite for decades! The professional company began as a traveling theatre company before making Bennington its home. The summer season will kick off on May 19th with “Shipwrecked,” followed by “Moonlight and Magnolias” and a whole season of delightful shows running through mid October!

Dorset Theater Festival season runs from June to September with performances of the country’s most talented playwrights, actors, and directors taking place on four different stages. Located in Dorset, approximately one half an hour from our Inn, it is well worth the visit!

Weston Playhouse Theater has been located in Weston for 80 years!  They are an award-winning regional theater group recognized nationally for its many programs. Every summer, people travel from all over to see their multistage summer festival! Weston Playhouse Theater is a beautiful 45 minute drive from the inn.

Each summer, the Williamstown Theater Festival takes place in Williamstown, less than a half hour from the Inn. The festival has performances from June to August, with both classic and new modern plays performed each month.

Oldcastle Theater Co.

Photo Credit: Oldcastle Theater Co.


A full spectrum art center, The Bennington has hosted some of the finest art exhibitions and organizations in the country, including the Plein Air Painters of America, the American Watercolor Society, the New England Watercolor Society, the Allied Artists of America, and many more!

Located in Williamstown, Clark Art Institute is one of the few institutions dedicated to displaying beautiful works of art in their museum, as well as being a center for research and higher education. The Clark Collection displays American and European paintings, drawings, prints, sculptures, and decorative arts from the Renaissance to the mid-20s.

MASS MoCA is a gallery that embraces all art forms including music, sculpture, dance, film, painting, photography, theater, and more. Located in North Adams, MASS MoCA not only features beautiful works of art, but they also have a full restaurant, various cafes, and a microbrewery! It’s the perfect place to spend the day.

The Clark Institute

The Clark Institute, Photo Credit: Tucket Bair

Music and Dance

Tanglewood is one of the world’s most beloved music festivals organized by the Boston Symphony Orchestra. This one-of-a-kind music festival takes place from mid-June to Labor Day. The new featured event this year will be Tanglewood Takes Flight, a collaboration of music and bird watching walks! Plus, don’t miss musical legends like James Taylor, Diana Ross, and Sting!

The world’s longest running dance festival, Jacobs Pillow, takes place every summer in Becket! This year is they’re celebrating their 85th year and they have an incredible event lined up for the occasion. Tanglewood and Jacobs Pillow are approximately one hour from the Inn.

Hubbard Hall, located in Cambridge, New York is located less than 30 minutes from our Inn. They showcase theater, music, dance, and visual arts performances. Hubbard Hall is a nonprofit organization focused on community-based arts.

Tanglewood at Dusk

Tanglewood at Dusk, Photo Credit: Stu Rosner

Book your stay at Four Chimneys Inn today and experience all of the amazing arts scene in and around Bennington.