Great Barrington, Massachusetts
Why it's so great: Calling Great Barrington the "big city" of Southern Berkshire County would be a stretch, especially considering that the town has a population of 7,000. But there's plenty going on here, including shows, movies, and concerts at the Mahaiwe Performing Arts Center, locally owned shops and galleries, and a ton of restaurants and cafes. Also, you won't forget you're in the Berkshires: it's part of the Appalachian Trail Community, and you don't even need to leave town for skiing or snowboarding in the winter at Ski Butternut.
Must-eat food: Prairie Whale has become a hit thanks to its fried chicken and cocktails. If you ask locals, they'll probably tell you that the inventive menu at Allium makes it their go-to spot for great dinners (especially the pizza or gnocchi).