There’s something about The Berkshires that just feels different—the perfect blend of small-town charm, culture, and those signature views that never get old. Whether you’re starting your morning with a locally roasted coffee, wandering through the gardens of a historic estate, or catching golden hour at Tanglewood, The Berkshires has a way of making every moment feel special. As a photographer deeply rooted in this community, I know the best spots to soak it all in. So, if you’re looking to experience the area like a true insider, here’s how to spend the perfect day in this corner of the Berkshires.

 

 

Shire Home Co

Berkshire Valley Inn

Williamstown, MA

Kemble Inn

Lenox, MA

 

Inn at Stockbridge

Stockbridge, MA

 

Evergreen Properties

Doctor Sax House

Lenox, MA

Roses Restaurant

Lee, MA

Alta

Lenox,MA

Public

North Adams, MA

Mezze

Williamstown, MA

District

Pittsfield, MA

Fluff

Great Barrington, MA

Arcadian Shop

Lenox, MA

Nature’s Closet 

Williamstown, MA

Berkshire Yoga Dance & Fitness

Pittsfield, MA

Miraval

Lenox, MA

Tanglewood

Lenox, MA

Kripalu

Stockbridge, MA

Canyon Ranch

Lenox, MA