My Itinerary
Click the heart to favorite travel ideas and inspo. Then copy/share your itinerary to save your favorites for when you’re ready to book the perfect Berkshire getaway.
Share Link
No favorites have been saved
Life in the Berkshires
Photo by Marina Dominguez. Courtesy of Downtown Pittsfield Inc. Things to Do
Revolutionary Berkshires: History, Art, and Community at America 250
Published on July 09, 2026
Read More
Arts and Culture
Early Summer is the Ultimate Season-Opening Celebration
Published on July 09, 2026
Read More
Things to Do
Rediscover Your Freedoms in the Berkshires This Summer
Published on June 30, 2026
Read More
Seán Curran Company & Darrah Carr Dance perform at Jacob's Pillow. Photo by Christopher Duggan. 