I’ve traveled the world, but never to the Berkshires in Massachusetts and so I let a concert in Tanglewood and the Food and Wine Extravaganza be my reason to spend a weekend away.

How did I pull this off and how did it go? Here’s how I handled the key challenges on this trip and what I learned.

Challenge 1 - Hotels were on the pricey side.
I decided to try Airbnb. I found an affordable room in Pittsfield in the home of two realtors and from the description and photos provided my gut told me...