Top 10 Scenic Vistas in the Berkshires

Winter is a great time to see the top 10 scenic vistas in the Berkshires. The lush landscape of western Massachusetts blanketed in a fresh layer of snow is equally as beautiful in winter as in any season. Yes, you’ll need a coat, mittens, a hat, and boots to fully appreciate the great outdoors. But the rewards of bundling up far outweigh the inconvenience of layering up to play outside comfortably. And remember, when you’re done playing outside, you can return to the warmth and luxury of our elegant country retreat in Lee, MA.

Skiing, snowboarding, and snowshoeing may top the list for avid winter sports enthusiasts. And the Berkshires has more than its fair share of spots to shush, glide, and trek. But you’ll also find great places to dash through the snow on a toboggan or sled or take a spin on an indoor or outdoor skating rink. There’s a reason visitors flock to the Berkshires after the holidays. It’s a veritable winter wonderland.

Although playing in the snow holds a great deal of appeal for some, the sheer beauty of the Berkshires draws many simply for the picture-perfect vistas found everywhere. Hop in the car and explore the charming towns and villages that dot the countryside. Indoors or out, a visit to these top ten scenic vistas in the Berkshires should be on everyone’s winter bucket list.

Hilltop Orchards and Furnace Brook Winery

Sip and swirl some fabulous wine and cider at the Hilltop Orchards and Furnace Brook Winery after an exhilarating cross-country ski adventure on this beautiful 200-acre orchard.
Location: 508 Canaan Road, Richmond, MA 01254


The former home of a wealthy lawyer, the historic home, and the public garden of the Naumkeag reflects the beauty and splendor of the Gilded Age.
Location: 5 Prospect Hill Rd, Stockbridge, MA 01262

The Mount

Edith Wharton’s historic estate in Lenox is a lasting tribute to a prolific author and her passion for gardening.
Location: 2 Plunkett St, Lenox, MA 01240

Norman Rockwell Museum

The Norman Rockwell Museum itself provides a fascinating look into the life and works of this American artist. But the grounds and views are equally impressive.
Location: 9 Glendale Road, Route 183, Stockbridge, MA 01262

Monument Mountain

The view from the summit of this very popular Monument Mountain spans the Housatonic River Valley.
Location: Route 7, Great Barrington, MA 01230

Mount Greylock

The highest elevation in the state, Mount Greylock is open all year for hiking, biking, cross-country skiing, and snowmobiling.
Location: 30 Rockwell Road, Lanesborough, MA 01237

Pleasant Valley Wildlife Sanctuary

Operated by the Massachusetts Audubon Society, Pleasant Valley Wildlife Sanctuary offers miles of trails to hike, including a steep climb to the apex of Lenox Mountain.
Location: 472 West Mountain Road, Lenox, MA 01240

Jiminy Peak

This 4-season resort located in Hancock, MA, is a haven for winter sports enthusiasts. Beyond the slopes, enjoy an alpine slide, scenic chair lift, and miles of hiking trails.
Location: 37 Corey Road, Hancock, MA 01237

Bash Bish Falls

Even on a winter’s day, the hike into view the thundering cascade of water at Bash Bish Falls amazes. Twin falls spill down an 80-foot drop into a clear crystal pool.
Location: Mt. Washington, MA

Olivia’s Overlook

The spectacular view at the stunning Olivia’s Overlook in the Berkshires reveals itself the moment you enter the parking lot. Two scenic trails wind through the woods right from the overlook.
Location: Yokun Ridge South, Hiking Trails, West Stockbridge, MA 01266

Everyone needs a change of scenery every now and again. So, make plans to visit us in winter and check out our top 10 scenic vistas in the Berkshires. Book a room at the Devonfield Inn and remember to pack your woolies.