(JNS) — It’s been a scorcher of a summer, so when a friend suggested a trip to the Berkshire Mountains, this Northeasterner was ready for some cooler weather. Not quite a “staycation” (it was about a five-hour drive during less trafficked hours), it was far less expensive than flying right now.

The Berkshires in Western Massachusetts is rustic and rural, offering the feeling of really getting away from it all. Little towns and villages are nestled in the mountains, a skier’s attraction come wintertime. In July, verdant greenery and clean air—coupled with thriving arts and cultur...