1. The Berkshires, Massachusetts
![The Berkshires, Massachusetts The Berkshires, Massachusetts](https://media.timeout.com/images/106156773/750/422/image.jpg)
![The Berkshires, Massachusetts The Berkshires, Massachusetts](https://media.timeout.com/images/106156773/750/562/image.jpg)
Located in western Massachusetts, the Berkshires are a true winter wonderland, and travelers can choose from an array of cold-weather activities. However, I prefer visiting in the summer, when the warm weather allows me to stroll through its picturesque towns (Great Barrington, Lenox and Stockbridge are personal favorites), sans heavy winter gear. I also enjoy getting out on the water—the region is home to nearly 60 lakes, many of which are great for boating, swimming, and fishing. Hiking opps also abound, including Mount Greylock, Massachusetts’ highest point. Theater-goers and music lovers will also enjoy a summer trip here: Each season, the Boston Symphony Orchestra takes over Tanglewood, which also offers an array of al fresco concerts from renowned artists like James Taylor; plus, the Barrington Stage Company puts on an abundance of performances all summer long.