I've lived in Great Barrington for 17 years and been to Searles twice. It's such a treat to go inside. Currently, it acts as a private school for youth with disciplinary issues, learning disabilities, etc. But occasionally they open up the Castle for fundraising events like concerts or tours. The yards and exterior are still beautifully kept, although parts of the inside definitely feel stuck in the '70s and a bit neglected. The John Dewey Academy students are in charge of interior cleaning and maintenance. But still amazing to see the gaudy dining hall spaces and experience Searles' deteriorating legacy.
It's great to experience many facets of Rockwell's life in conjunction. His museum is just a short ride away from his historic studio space in Stockbridge, MA and many sites featured in his work. The museum is a great half-day trip and covers a huge breadth of his work!
I've lived in the Berkshires for 16 years, and the Dream Away Lodge is by far my favorite place to eat and listen to music. Legends have played there and the small audiences that go there today are always a great mix of locals and tourists alike. With a quirky bar and delicious food, Dream Away is a destination you can plan to be at for many hours. The nights tend to end with great conversations and music shared with strangers around a campfire. One of a kind experience.