Into the Wild

Tucked into the rolling hills of Western Massachusetts, the Berkshires region is an outdoors delight.

The term “Rockwellian” refers to the quaint and sentimental style Norman Rockwell used in his portrayals of American life. Once you experience the rich culture and natural beauty of the Berkshires, it becomes clear why the famed illustrator, who lived in this region during his later years, never lacked for inspiration.

Tucked into the rolling hills of western Massachusetts, the Berkshires is an area that attracted artists long before Rockwell moved there in 1953. At the turn of the century, the picturesque villages and towns lured writers, dancers, performers and musicians. Around the same time, the captivating countryside welcomed some of America’s wealthiest Gilded Age families from Boston and New York. Though known for building Newport mansions to escape the city swelter, titans of industry also were drawn to the Berkshires, where they built great estates in calm, pastoral surroundings refreshed by the crisp mountain air.

The town of Lenox became known as “the queen of inland resorts” and later, the vibrant, affluent community became home to Tanglewood, the music center that has served as the summer home of the Boston Symphony Orchestra since 1938.
Only a fraction of these mansions (which are ironically called “cottages”) survive today. Those that remain have been turned into luxury resorts and museums. Among them is Blantyre, an ivy-covered Tudor-style mansion in Lenox that dates back to 1901. More than a century after serving as a private home to a wealthy oil industrialist, Blantyre has been transformed into a lavish Relais & Chateaux retreat that Condé Nast has named one of the Top 100 Hotels in the world. Though the main house indulges the senses with richly burnished woods, posh suites and leaded glass windows, it is the four cottages and The Carriage House that offer a truly secluded escape. The only problem is that the Berkshires is a place entirely too inviting to stay indoors.

One such enticement is Mount Greylock, the highest peak in the state. It offers an array of hiking trails, including a rugged, 11-mile section of the Appalachian Trail. Just pick up complimentary maps at the visitor center at Mount Greylock State Reservation in Lanesborough and you’re on your way. The base-to-summit hike is an all-day affair, so if you’re short on time, you can drive part of the way and then hop on a shorter trail that leads to the peak, where you’ll be rewarded handsomely with spectacular views.

Literary luminaries such as Herman Melville, Nathaniel Hawthorne and Henry David Thoreau made the hike in the 1800s. In fact, Melville enjoyed views of Mount Greylock from his home, Arrowhead, located in nearby Pittsfield. Arrowhead is now a National Historic Landmark that is owned and operated by the Berkshire County Historical Society. The organization offers guided tours of his 18th-century farmhouse, including the library where he wrote Moby Dick.

Adrenaline junkies will want to experience nearby Ramblewild, an aptly named aerial ropes adventure course with 120-foot-high treks over a sustainable forest. But the park can also be a family affair, as it is designed to accommodate all levels of comfort and fitness, with guided hikes ranging from leisurely to adventurous. In the winter months, there are snowshoeing tours for newcomers and experienced trailblazers. All ground expeditions are led by guides who double as local historians, so you’ll listen to tales of the area’s past while walking among indigenous tree and plant species.

There are many businesses in the Berkshires that offer outdoor pursuits, including downhill and cross-country skiing, tubing, ice skating and snowshoeing. Once the ground thaws, nearly a dozen golf courses become ready for play, including Berkshire Hills Country Club, the only A.W. Tillinghast design in Massachusetts.

Lenox is also home to the Cranwell Spa & Golf Resort, which is located less than three miles from Tanglewood. This historic 18-hole course combines spectacular views with challenging golf. The tree-lined fairways and naturally contoured greens have been carefully preserved since the course was built by Wayne Stiles and John Van Kleek in 1926.

Journey 45 minutes south to Southwick and you’ll come upon The Ranch Golf Club, a spectacular venue that has earned plaudits from national publications since opening in 2002. The course was created on an historic piece of land and flows through a mixture of open meadows and woodlands, interspersed with beautiful water features to make each hole exciting and memorable.

Those looking for spiritual renewal amid nature should visit the National Shrine of The Divine Mercy, on Eden Hill in Stockbridge. Welcoming pilgrims from around the world for decades, the 350-acre campus includes the exquisite Shrine Chapel, outdoor grottos and tranquil groves in addition to other places to relax, reflect and reconnect.

Any trek to the Berkshires would not be complete without savoring the local flavors. There is no shortage of restaurants with chefs who source from local farms and food artisans. John Andrews Restaurant in South Egremont is home to a “Featured Farm Prix Fixe” menu that offers a three-course dining experience highlighting seasonal ingredients from farms and food artisans from the Berkshires, Hudson Valley and northwestern Connecticut. The restaurant is part of Berkshire Grown, a network that links farmers with the Berkshires community.

But enjoying the spoils of local growers can also be relished in the most casual sense. How We Roll is an inventive farm-to-table food truck with a menu consisting of from-scratch comfort food conveniently stuffed egg roll-style, flash fried and ready to devour. The truck is based in Pittsfield, but devotees know to follow it on Twitter (@HowWeRollShire) for its latest locale.

If you’re seeking to relax, refresh and recharge, to reacquaint with small-town America or for a recreational Utopia to challenge your physical senses, the Berkshires promises to offer a memorable adventure.