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.

PLACES TO STAY:

Berkshire Valley Inn

Williamstown, MA

Kemble Inn

Inn at Stockbridge

Stockbridge, MA

Evergreen Properties

Shire Home Co

GRAB A MEAL
Roses Restaurant

Lee, MA

Alta

Lenox,MA

Miraval

Lenox, MA

Public

North Adams, MA

Mezze

Williamstown, MA

VISIT

Tanglewood

Lenox, MA

GRAB A DRINK

Doctor Sax House

Lenox, MA

District

Pittsfield, MA

SHOPPING
Fluff

Great Barrington, MA

Arcadian Shop

Lenox, MA

Nature’s Closet 

Williamstown, MA

TAKE A CLASS

Berkshire Yoga Dance & Fitness

Pittsfield, MA

Kripalu

Stockbridge, MA

Canyon Ranch

Lenox, MA