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Best Things to do in the Berkshires

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The Berkshires is one of those places that nicely fits our idea of a well-balanced destination. There’s a rare and beautiful union of varied things to do in the Berkshires. The list includes adventurous outdoor activities, awe-inspiring nature, interesting history, a vibrant arts and culture scene, and plenty of self-pampering distractions.

For decades this special slice of western Massachusetts has been inspiring as many literary, visual, and performing artists as it has nature-lovers and outdoor adventurers.  

Iconic Americana artist Norman Rockwell and Hermann Melville, author of Moby Dick, were each inspired to work on their art in the beautiful Berkshires. Also, Edith Wharton, first woman to win a Pulitzer Prize for literature, chose to live and hone her craft in the “Shire”, as the locals call it. 

Perhaps their legacy is partly why today the Berkshires is known and loved for the many museums, galleries and performance centers.

The Berkshires is also home to many examples of the bygone era of America’s Gilded Age. This Gilded Age (a term attributed to Mark Twain) took place in the late 1800’s following the Civil War. 

Economic growth and industrialization allowed a select few to become very wealthy very quickly. This wealth was displayed in the Berkshires with the building of large estates, inappropriately called “cottages” These estates served as second home getaways for the newly wealthy from New York and Boston.

The draw for outdoor enthusiasts is evident everywhere you go in the Berkshires. Here you’ll find majestic mountain vistas and rolling hills, an abundance of lakes and rivers, quiet roads winding through scenic meadows and farmland, plus woodland that turns into a kaleidoscope of color in the fall.

Notice: Due to the worldwide health crisis in 2020 some of the following venues and events may have closures and restrictions. Please check in advance for special hours and follow the required and suggested precautions.

Where to stay in the Berkshires, MA

Town in the Berkshires

The Berkshires have more than a fair share of charming New England towns and villages, each with an array of accommodations to suit even the most discerning taste. While the Berkshires is not known as a budget destination there are certainly options for every price point. From basic motels to quaint inns and even a Scottish Castle you’ll find it here.

Vacation Villages in the Berkshires

The first thing to decide is which of the lovely vacation villages in the Berkshires to call home. Lenox and Stockbridge are often considered the prettiest of these classic New England towns. Therefore they are very popular as a home base for exploring the region. 

Stockbridge was the home of Norman Rockwell for the last 25 years of his life. Some of his beloved paintings portraying daily life in small-town America were inspired by the town and its residents. Lenox was once the favored location for summer homes of the likes of the Vanderbilts, Carnegies, and Westinghouses.

Though a small town itself, Great Barrington is the “big city” of the Berkshires. Here you’ll find history, charm, and an abundance of dining and entertainment options. Pittsfield, known as the “City of Festivals”, is the largest town in the Berkshires. There’s almost tangible energy here flowing from the array of visual and performing arts on offer.

There’s also North Adams, the “The Town of Steeples and Peaks”, Williamstown “The Village Beautiful”, and Lee, a place for shopping, dining, and lake-based activities. Wherever you choose to stay you will find charm and warm hospitality.

Inns in the Berkshires

Similar to the popular coastal area of Cape Cod, there’s a wide assortment of vacation accommodations in the Berkshires. However, for the full New England experience we suggest staying at one of the iconic inns in the Berkshires. Many of these inns hail from the Gilded Age mentioned above.

The Stockbridge Inn dates back to the early 1900s but has been beautifully renovated by the welcoming innkeepers. Also in Stockbridge is the Red Lion Inn, built in 1773, which offers 82 rooms each uniquely decorated with antiques.

In North Adams, The Porches Inn comprises Victorian row houses with modernized interiors. Pleasant surprises, such as a birdcage elevator turned cocktail bar, await at Hotel on North in Pittsfield. Then there’s Great Barrington’s, The Old Inn on the Green which is a refurbished 16th-century stagecoach stop.

Lenox has an impressive selection of lovely Berkshire inns and lodges. The grand estate of Wheatleigh was built in 1893 in the style of a 16th-century Italian palazzo for the daughter of a tycoon. The award-winning Gateways Inn has 11 beautifully decorated rooms along with a gorgeous mahogany bar. 

You can even stay in a Scottish castle just outside of Lenox. Blantyre was built for millionaire Robert Paterson in 1901 and was named and modeled after his mother’s home in Scotland. The Tudor-style facade exudes romance complete with ivy-covered stone walls and fairy-tale turrets.

Note: Blantyre is adult only so plan to have a child-free getaway if you stay here.

Outdoor Activities

Hiking trail in the Berkshires

The list of natural sights and outdoor activities in the Berkshires is almost endless. But here’s a few ideas of outdoor things to do in the Berkshires to get you started with your vacation plans.

Hiking in the Berkshires

One of the best ways to really experience this natural New England beauty is by hiking some of the 400+ trails in the Berkshires. Trails are varied in length, difficulty, and accessibility so there’s something for every hiking level and many are open year-round. 

For animal lovers, there are even trails leading to and through wildlife sanctuaries. Spend some time at Mass Audobon’s Pleasant Valley Wildlife Sanctuary where there are 7 miles of trails (many are wheelchair accessible) with amazing vistas and wildlife spotting.

Some easy options for all ages and levels are Olivia’s Lookout at Yokun Ridge near Stockbridge and Housatonic Flats in Great Barrington. Kick it up a notch by hiking Bob’s Trail, Hoosac Range, or Basin Pond. 

Another option is to head to Monument Mountain where you’ll find several trails of varying degrees. Challenge yourself and be rewarded with stunning views by hiking the 720-foot elevation gain up to Squaw Peak.

Tip: There’s an informative list of trails on the Berkshire Natural Resources Council website.

Biking in the Berkshires

Cycling is another great way to explore the Berkshires. The beautiful rolling countryside and abundance of good main and tertiary roads make this area a favorite of road cyclists from all over the country.

Many of the hiking trails listed above are also suitable for cycling. Plus there’s some great mountain biking terrain, especially in Pittsfield State Forest. You can even find downhill biking on Thunder Mountain at Berkshire East Ski Resort.

Tip: Bike New England has a great list of bicycle rides in the Berkshires.

New England Leaf Peeping 

Fall in New England is a kaleidoscope of color. The Berkshires in particular is a leaf peepers dream getaway. Hiking and biking are the preferred modes of movement to fully immerse yourself in the magnificent fall foliage this area is known for. 

Many of the hiking trails mentioned above are good options for leaf-peeping, especially the Monument Mountain summit with a 360-degree view. For something less strenuous but still with stunning colorful vistas head to Mahanna Cobble summit on Lenox Mountain

If you prefer to peep by car there are plenty of scenic drives around the Berkshires where fall colors are plentiful. A couple of favorites are the Central Berkshire Loop and the South Central Berkshire Route. Furthermore, you can drive to the summit of Mount Greylock which is the highest point in Massachusetts for a view of the autumn colors sometimes of up to 90 miles.

More Berkshire Things to do Outdoors

Whether you’re an adrenaline junkie, a photographer, a nature-lover and wildlife watcher or someone who enjoys countryside drives with stops at local farms you will fall in love with this piece of New England.

One of the most popular drives in the Berkshires is along Route 7 from Sheffield to North Adams. The actual drive time is about 90 minutes but foodies and photographers will likely double or triple that time to allow for many stops and side road detours along the way. 

Highlights of this drive, with detours, include iconic Americana scenes of farmhouses and barns sitting in picturesque fields with a backdrop of rolling hills and Berkshire mountains. Furthermore, Mount Greylock and Monument Mountain can be reached from this route. 

The road also crosses the Housatonic River, passes colorful forests, and offers an opportunity to veer off at Mount Everett State Reservation and on to see Bash Bish Falls State Park which is definitely worth the extra time. 

To complement the scenery there are numerous inns, cafes, farms, orchards, cideries, and Sugar Shacks (maple syrup farms). These make great pit stops along the country roads as well as in the Berkshire villages mentioned above. Consider pulling into little Lanesborough and stop at Lakeview Orchard for their famous fresh baked apple cider doughnuts washed down with fresh-pressed apple cider.

If you’re after a bit more adventure and physical activity consider a visit to Ramblewild, a large aerial adventure park with 11 acres of ziplines, climbing and swinging adventures. Jiminy Peak Mountain Resort also has an aerial park, an alpine slide and a rock-climbing wall in the warmer months plus skiing and snowboarding in the winter.

History, Arts, & Culture

Stairs at Naumkeag Berkshires

As mentioned in the opening of this post the Berkshires is a hotbed of arts and culture, home to some wonderful historic buildings and full of interesting stories of previous residents and visitors. 

So let’s dig a little deeper into some of the cultural experiences you will find in the Berkshires.

Festivals & Theater in the Berkshires

The Berkshires has several performance theatres and a slew of music events and festivals that go on year-round.

Tanglewood is an open air music venue and is also summer home to the Boston Symphony Orchestra. It attracts music lovers of all genres and has hosted concerts since 1937 from a diverse group of performers from Yo Yo Ma to Janis Joplin. Bring a picnic and enjoy a concert on the sprawling lawn.

Jacob’s Pillow is a 225-acre National Historic Landmark and nationally acclaimed dance training center. This beautiful site hosts a 2-month long summer dance festival where outdoor performances can be enjoyed with the scenic natural backdrop.

The Williamstown Theater Festival draws stars like Bradley Cooper and Christopher Walken to the stage during the summer-long event. Performances are top-level and some of the plays debuting here move on to Broadway.

Other performance arts centers and groups to check out are Colonial Theater in Pittsfield. The Berkshire Theater Group, Chester Theater Company, and the Mahaiwe Performing Arts Center. 

Historic Landmarks & Museums in the Berkshires

There is such a plethora of museums in the Berkshires there’s bound to be something for every interest. Here’s just a sampling of fascinating and educational opportunities.

Herman Melville chose Pittsfield as home from 1850 to 1863 and it was here that he wrote Moby-Dick. Arrowhead was the house he lived and wrote in and is now a museum of his life here. You can tour the house and grounds led by uber informative and passionate guides. 

One of the most unique “cottages” of the Gilded Age is Naumkeag. This quirky mansion was built for a wealthy NY corporate lawyer by architect Stanford White. White apparently hated square rooms so he designed the building with lots of angles and curves. There are also beautiful gardens to wander.

Beloved American artist Norman Rockwell lived in Stockbridge for the last 25 years of his life and there’s a fabulous museum dedicated to his work. A tour of the Norman Rockwell Museum will take you through his interesting creative process which included working with fellow Stockbridge residents who he used as models for his paintings.

The Mount was once home to the literary queen, Edith Wharton. The house has been restored to near original, and Wharton herself designed the stunning formal gardens and landscaping.

In North Adams, you’ll find the Massachusetts Museum of Contemporary Art, also known as MASS MoCA. The space, once a factory for atomic bomb triggers, is massive and exhibits diverse contemporary visual and performing arts. Along with permanent and temporary art installations, MASS MoCA also hosts nearly 100 live performances each year.

The small village of Williamsburg is home to one of the best art museums in the country. The Clark displays Impressionist and Renaissance masterpieces, American 18-century furniture, and an impressive collection of silver and fine porcelain. There’s a lot to see and taking a tour is very worthwhile.

Some other noteworthy historic sites and museums in the Berkshires are Chesterwood, the Berkshire Museum, Ventfort Hall Mansion and Gilded Age Museum, and Hancock Shaker Village. A more complete list can be found at Berkshire’s official website.

Spoil Yourself

Fine dining meal with wine

As already noted, the Berkshires is a rare confluence of distractions. So, this article would not be complete without a mention of the many ways to pamper yourself.

Wellness in the Berkshires

For decades people have been heading to the Berkshires to renew and rejuvenate. Along with the therapeutic effects of nature this destination also offers an abundance of spas, retreats, yoga and wellness centers.

Canyon Ranch is an upscale spa resort offering everything you need to relax and revive. It does come with a high price tag though so it’s not for everyone. Then there’s Cranwell Spa & Golf Resort which is home to the Spa at Cranwell, one of the largest spas in the Northeast.

Kripalu Center for Yoga and Health has been providing holistic wellness experiences for more than 40 years. Choose from weekend retreats, multi-day full programs, and day sessions.

For more casual and active retreats take a look at the year-round offerings at Berkshire Outdoor Center and the events at Race Brook lodge.

Dining in the Berkshires

As with nature and culture experiences there’s also no shortage of great places to eat in the Berkshires. Cute cafes, American diners, romantic meals at historic inns, fresh food markets, and amazing farm to table experiences are just a sampling of what you’ll find. 

Plus, to accompany that delicious food are libations and refreshments from local apple orchards, wineries, and craft breweries.

There are far too many restaurant choices to mention here, but for a special Berkshire experience look for a farm to table menu with a New England ambience. Following are some highly recommended dining experiences:

The owner of Old Inn on the Green is also a chef who creates fabulous menus from fresh locally sourced food. In the summer you can dine al fresco under a garden canopy and in the winter the dining room is lit by fire and flickering candlelight.

Mezze Bistro & Bar is often named as one of the best restaurants in New England. It’s a bistro-style restaurant with a seasonally changing menu set in a lovely historic house.

Step back in time with a meal at the Red Lion Inn. The hotel was first opened in 1773 and now offers four on site dining experiences. The main dining room is the most atmospheric with red carpeting, floral wallpaper and fine china.

Table Six Restaurant is found inside the Kemble Inn, a beautiful Gilded Age mansion. They have stunning views, a romantic setting and a very special Sunday brunch. 

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