Worth getting out of bed for...

Viewpoint

If you’ve a head for hikes, there’s nowhere better for admiring that unmistakable New England landscape than Squaw Point on Monument Mountain, located just outside Great Barrington. There are three miles of trails, but it’s worth the exertion for the spectacular tree-canopy panorama from 1,680-feet. If all this talk of feet is tiring you out, opt instead for a train tour of the Berkshires on the the Berkshire Scenic Railway (www.berkshirescenicrailroad.org) in a 1920s era passenger car.

Arts and culture

Visual arts are high up on the cultural agenda. Located on the grounds of an old factory, the Massachusetts Museum of Contemporary Arts (www.massmoca.org) is known for its cutting-edge (and sometimes controversial) exhibits. The largest centre for contemporary visual art in the country, the museum’s buildings also host films, dance, and music performances. The Norman Rockwell Museum in Stockbridge (www.mrm.org) holds a huge number of the celebrated artist’s most famous illustrations.

Something for nothing

For a dance-themed day out, visit the world-renowned School at Jacob’s Pillow (www.jacobspillow.org), where you can observe classes in progress, admire the dance exhibitions in the school’s Blake’s Barn, attend pre-performance talks, or conduct a self-guided tour of the 163-acre grounds.

Shopping

If you’re on the hunt for arts, rustic crafts or farm-fresh foods, you couldn’t choose a better spot – Pittsfield, Great Barrington and Stockbridge, especially. For hand-thrown and glazed stoneware inspired by the scenery, try The Berkshire Pottery off Route 23 in Hillsdale (+1 518 325 4567; www.berkshirepottery.com). Joel Hotchkiss, owner of the whimsical Hotchkiss Mobiles Gallery & Café (+1 413 232 0200; www.artmobiles.com) on Centre Street in West Stockbridge, creates the delciate, colourful mobiles you can buy in the New York Guggenheim. Also in Stockbridge, the vibrant Origins Gallery (+1 413 298 0002) on Main Street sells unusual art and antiquities from around the world, including African art, Chinese furniture, and Mexican processional statues. Great Barrington’s Yellow House Books (+1 413 528 8227) is a local institution – not only does it sells a fabulous selection of used books and monographs, but it also boasts an in-house band, who regularly perform on the store’s porch.

Daytripper

The Berkshires is a cradle of American literature, especially in the 19th- and early 20th centuries. Local luminaries include Edna St. Vincent Millay, Herman Melville, and Edith Wharton – all of whose houses are now open to the public. Make a day of it, and start with Millay’s Steepletop, (www.millaysociety.org), an isolated farmhouse in Austerlitz, New York, then move on to Melville’s mountainside Arrowhead (www.mobydick.org) in Pittsfield, the end your whistlestop literary trot with Wharton’s landscaped estate in Lenox.

Best beach

Just because you’re miles from the Atlantic coast doesn’t mean you have to miss the beach. The town of Stockbridge has sculpted a small golden beach on the shores of the Stockbridge Bowl lake. Although there’s a nominal residents-only rule, it’s rarely enforced.

Perfect picnic

Pack up your picnic provisions from Guido’s Fresh Marketplace (www.guidosfreshmarketplace.com) in South Street, Pittsfield (there’s a branch in Great Barrington too), then continue for several miles to the Wahconah Falls State Park, and enjoy an alfresco lunch at beside the roaring 40-foot falls.

Walks

The Pleasant Valley Wildlife Sanctuary near Lenox, is precisely that, making it ideal for leisurely wandering around its trails. Follow the Yokun Brook through the pine forest and look out for beavers, or head there in Spring to catch the annual Salamander migration along West Mountain Road.

Children

Take the tykes on a quarter-mile walk in the Dinosaur Footprints Park off Route 5 in Holyoke to see the three-toed fossilised footprints of Eubrontes giganteus, who left his mark on the mud almost 200 million years ago. Despite the community’s strict policies on celibacy, the Hancock Shaker Village (www.hancockshakervillage.org) near Pittsfield is totally family-friendly, and offers youngsters an opportunity to learn about traditional Shaker crafts and furniture-making, stroke farm animals, ride horse-drawn wagons, and explore the life of America’s early Protestant settlers. Green River Farms (www.greenriverfarms.com) in Williamstown, has a petting zoo too, with the addition of a corn maze (or rather, a maize maze) and picnic trails.

Activities

In the summer pick your own blueberries, and in the fall pick your own apples at Windy Hill Farm (+1 413 298 3217) in Great Barrington. Hike the hills with guide Kevin Parsons and visit lesser-known vistas as you learn about the region’s early American history. Enlist the in-demand services of Green Woods Guided Hikes (www.GreenWoodsHikes.com), which even provides post-hike massages. Can’t ski, but want to enjoy the winter slopes? Ski Butternut (www.SkiButternut.com) has a centre dedicated to the fine art of inner tubing, as well as 22 slopes and a professional ski school. Winter weekends only.

And

Tanglewood is synonymous with the Berkshires. The estate is the summer home of the Boston Symphony Orchestra and each summer hosts a sonic extravagnaza of opera, classical, pop and jazz concerts from June to early September. For something special, pack a picnic breakfast and enjoy a rehearsal ($17 a ticket) and you’ll feel like they’re playing a concert just for you.