With something to entice a visit in all four seasons, the Berkshires welcomes visitors in winter, spring, summer, and fall. But what is the best time to visit the Berkshires? Well, that depends.
Every season spins its magic. Spring harkens new birth and a return to milder temperatures. Farms spring to life with a flurry of activity planting for summer and fall harvests. Summer seems to ease into a mellow mood of long, languid days and star-filled nights spent drinking in the abundance of cultural offerings.
When summer slips into fall, with a riot of color and fun festivals to entertain, the need to get outside and explore the natural world on two feet or two wheels takes center stage. And when old man winter finally comes calling, with a nip in the air and freshly fallen snow, it’s all about skiing, snowshoeing, and snowboarding for the thrill seekers and cozying up to a warm fire for those who prefer their chill indoors.
No matter what floats your boat, the Berkshires remain a premier destination every season. Blessed with mountains and valleys, quaint villages, and a bevy of world-class restaurants and bistros, western Massachusetts appeals to a host of travelers for its diversity of attractions peppered among one of the most beautiful destinations in the country.
So, let’s break it down season by season. We think you’ll find more than one reason to visit our elegant country retreat in spring, summer, fall, and winter.
Spring
“Spring is when you feel like whistling
even with a shoe full of slush.” —Doug Larson
The transition from winter to spring brings with it a bit of fickle weather. Snow showers and clouds may follow the sunshine and warm breezes. And ultimately, snowmelt brings mud to the mountains and fills waterfalls to overflowing. But the unfailing atmosphere is one of rebirth.
As the days turn warmer, yet the nights are still cool, maple sugaring season begins. Don’t miss Massachusetts Maple Weekend in March.
Among the most popular attractions in spring, gardens in bloom bring hope to winter-weary travelers. Everywhere you look, spring blossoms peek out from their winter hibernation, creating a colorful canvas across the region. The Berkshire Botanical Garden, open May through October, invites guests to wander freely among the various exhibits and landscaped grounds.
In spring, rivers and streams gush with snowmelt, and waterfalls cascade in earnest over granite outcroppings. Bash Bish Falls, the highest single-drop waterfall in the state, tempts visitors to trek through the woods for a chance to witness its twin cataracts thundering down to the crystal-clear pool below.
You’ll need a pair of sturdy boots to tackle some of the great hiking trails in the Berkshires. But your reward for accepting the challenge becomes apparent when you reach the summit of a mountain and revel in the vistas before you. If your taste leans towards easy to moderate exertion, try one of the varied trails that make up the Pleasant Valley Wildlife Sanctuary. A Mass Audubon Society property located in nearby Lenox, the trails here lead through dense forest, verdant meadows, and along the slopes of Lenox Mountain, with great opportunities to spot wildlife.
Of course, shopping features prominently on every vacation in any season, and the Berkshires have great spots to seek out when your outdoor adventures leave you needing an indoor break. Antiques, boutiques, bookstores, and outlets line western Massachusetts’s main streets and back roads, offering everything from designer duds to architectural salvage. And when hunger strikes, no doubt there’ll be a café or bistro ready to sate your appetite.
Summer
“Summertime is always the best of what might be.”
—Charles Bowden
Summer arrives with a burst of great anticipation. Windows and doors fling open to welcome the sunshine and balmy breezes. We trade our sweaters for shirtsleeves, shoes for sandals, and ski poles for golf clubs. The months stretch out before us with the promise of spending lazy days at the lake, afternoons, and evenings under a clear sky, enjoying the talented artists of Tanglewood, Jacob’s Pillow, or Shakespeare and Company.
The storied summer home of the Boston Symphony Orchestra (BSO), Tanglewood, is more than just a concert venue. Set among 500 acres between Lenox and Stockbridge, the campus includes the Tanglewood Music Center (TMC), a learning hub for musicians, singers, composers, and other emerging professionals. Mentored by world-class musicians and coached by resident faculty, students attending the Center are exposed to challenging coursework along with performances by visiting musicians.
Visitors are welcome to tour the grounds on their own year-round. Guided tours, offered in July and August, take visitors through the Koussevitzky Music Shed and Ozawa Hall, providing insight into the history of Tanglewood, the BSO, and the TMC.
The Popular Artist Series, one of the highlights of Tanglewood’s summer season, brings some of the world’s most engaging folk, rock, pop, and jazz performers to the rolling hills of the Berkshires. Featured in past years, James Taylor, Van Morrison, Ringo Starr, and Bonnie Raitt graced the stage for star-studded performances.
Tanglewood is one of many cultural venues that attract visitors in the summer months. World-class museums and theater festivals also compete for the attention of those who venture to western Massachusetts in the summer months. The Norman Rockwell Museum, The Mount, and Hancock Shaker Village stand out as first-rate destinations to visit as well.
But if your tastes lean more toward outdoor sports and adventure, the Berkshires also delivers in style. Pack your golf clubs, kayaks, hiking boots, and mountain bikes to test your mettle on our challenging golf courses, rivers, and hiking trails. In fact, with so many outstanding outdoor activities to pursue at your leisure, you may need to extend your stay or plan several trips to embrace them all.
Fall
“I cannot endure to waste anything
so precious as autumnal sunshine by staying in the house.”
—Nathaniel Hawthorne
Fall tantalizes everyone. And nowhere in the world does fall explode with a riot of color, funky fun festivals, and breathtaking scenic vistas as it does in the Berkshires. Imagine waking in the heart of the Berkshires to a brilliantly sunny day filled with endless opportunities to get outside and explore fields and forests painted in almost every hue of the rainbow. The best fall foliage hikes lay within minutes of our historic bed and breakfast. But how about linking your fall hike to finding a waterfall where you can witness torrents of water tumbling freely over rocks and boulders or cascading down granite faces? No worries. We’ve mapped a few idyllic hikes to waterfalls that fit the bill.
There’s no need to challenge yourself to an arduous mountain hike to see the brilliant colors of autumn in the Berkshires. Many of our most popular attractions offer gorgeous grounds to explore. Some of our favorite spots to find fall foliage come with the added interest of visiting a historic home or note-worthy museum.
What would fall be without a fun fall festival? Known for world-class concert halls, storied theaters, and a bevy of historic estates, the Berkshires also have a penchant for celebrating everything from ghosts and goblins to local legends. From September through October, the calendar is filled with festivities.
September in the Berkshires, in particular, is a great month to visit. The summer crowds thin, but the days remain warm and the nights brilliant with stars. It’s the perfect time to try one of our outdoor experiences, dine leisurely at the most popular restaurants, and take in some live performances at our local theaters and concert venues.
Though there may be a chill in the air, the home fires still burn at the Devonfield Inn, and the attractions you love in spring and summer still welcome visitors through the end of the year. Don’t discount the month of November for a trip to the rolling hills of the Berkshires. Take a drive along the Mohawk Trail with its twists and turns. Grab a fresh-pressed cider and a warm cider donut at Cider Days. And book your tickets for Nightwood at the Mount to get you in the groove for the holidays.
Winter
“Winter is the time for comfort, for good food and warmth,
for the touch of a friendly hand and for a talk beside the fire.”
—Edith Sitwell
Snow is inevitable in New England, which also holds true for the Berkshires. With a fresh layer of snow on the mountains and the woods dusted in white, the most pressing question is where to ski or snowboard. Fortunately, we are blessed with five great ski resorts to tempt every skill level. But if downhill is not your thing, pack your cross-country skis or snowshoes and set out to any one of 6 exhilarating spots to experience our winter wonderland.
We all remember sledding and tubing as a child, finding a gentle slope to sail down, then trudging back uphill to soar again; it sounds exhausting. Enter the creation of a snow tubing lift that will whisk you uphill on a magic carpet. Bousquet Mountain sports an 8-lane tubing hill with a 450-foot drop that will remind you of your childhood sledding days without all the exertion.
But what if spending winter outside leaves you cold? Consider taking to the hills to find some of the best craft brewers and wineries. The Berkshires is rapidly becoming a wine lovers’ destination with lovely tasting rooms and premium wines. Map a tour of five of our favorite wineries and tasting rooms and bring home a bottle or two to decant at home or in one of our luxurious accommodations at the Inn.
Similarly, touring local craft breweries for the beer lovers among you makes for a great way to wind through the back roads of the Berkshires in search of a great pale ale or an American IPA. Our guide to craft breweries in the Berkshires will give you a leg up on planning your tour. Naturally, we recommend designating a driver for any adventure that includes alcoholic beverages.
We can’t talk about winter in the Berkshires without mentioning the holiday festivities we look forward to every year. Sound and light shows, holiday markets, and historic home tours make the season bright. And what makes the holidays even more special in the Berkshires? A stay at our elegant country estate.
For even more ideas on maximizing your winter getaway, check out our blog, Top 5 Things to do in the Berkshires in Winter.
Get date ideas in the Berkshires by reading another one of our posts!
So, there you have it. To answer your question, what is the best time to visit the Berkshires? Anytime you get the chance.
