The Loaded Trunk was founded by Jonna Robison, an interior designer with a deep curiosity and passion for traveling the world, connecting with artisans in different cultures and sourcing unique and beautiful objets d’art. Published seasonally, the magazine features a curated collection of travel, lifestyle, nature, art and design inspiration for a life well lived.
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Autumn in the Berkshires is, quite simply, a delight to behold. The landscape, laden with hills and dales typical of New England, becomes a patchwork quilt of gold, scarlet and russet. Apple orchards lay out their harvest and some even offer freshly pressed apple cider and bake apple cider doughnuts, coated in cinnamon. My daughter and I spent a week this fall guzzling quarts of cider and munching on “just one more” apple cider doughnut as we crisscrossed the countryside, gathering (experiencing, really) gilded apples in the Berkshires.
This gorgeous pocket of Massachusetts, along the New York border, stretches from Williamstown in the north to Sheffield in the south, along historic Route 7. Historic towns are strung like pearls along this stretch of picturesque road, as well as the quiet roads that branch out. New York City can be reached 3 hours heading south and Boston is just 2 hours to the east.
I lived here for a stint with my husband, many years ago when we were in our twenties. It’s when I was first introduced to Edith Wharton and the mansions of the Gilded Age. During the late 1800’s wealthy New Yorkers escaped to their glorious estates in this exclusive enclave, much like Newport, Rhode Island.
Today, the laidback Berkshires attract those who seek peace and quiet, a rich art tradition, hiking, and gentle pursuits, such as spa and yoga retreats. Unlike the Hamptons, which draw those who desire to see and be seen, the Berkshires are understated, yet coated with a bit of restrained glamour. Hence, the gilded apples that make a visit so delicious and delightful.
Most of the towns and villages throughout the Berkshires were incorporated in the latter part of the 1700’s. A handful of the towns to include on your itinerary include Williamstown, home of Williams College and the exceptional Clark Art Institute.
Pittsfield is the largest town in the Berkshires and known for the historic Hancock Shaker Village, the living history museum about the Shakers. Arrowhead, the home of Herman Melville, is where the author lived and penned his masterpiece, Moby Dick.
Lenox is a most charming village that is home to many of the Gilded Age mansions, as well as Tanglewood, the summer home of the Boston Pops Orchestra. Shops, galleries and restaurants line the streets. The area is also known for its destination spas, historic inns and hiking trails. The beautiful Church on the Hill stands above the village and the handsome Lenox Library, which has stood here since 1815.
Picturesque Stockbridge has a quaint main street running through town, lined with shops and cafes and the unmissable Red Lion Inn. The Red Lion has been operating since 1773, when it was established as a little tavern stop for stagecoaches. Nearby are some fantastic museums, the Berkshire Botanical Garden and historical homes open for visitors to tour.
Great Barrington is bustling with shops, restaurants and the Mahaiwe Performing Arts Center. There is some fantastic hiking in the area with stunning views of the valley and mountains beyond.
Pastoral Sheffield is most recognizable for its concentration of antique shops and the reconstructed Old Covered Bridge, which used to be the oldest covered bridge in Massachusetts until it was destroyed in a fire.
It’s easy to see why the top tier of the 19th century drove their horses and carriages or loaded their large leather trunks onto train carriages (yes, trains chugged from New York to the Berkshires back in the day!) and built imposing mansions in this beautiful landscape in and around the charming village of Lenox. Several estates have been restored to their full glory, while others are undergoing meticulous renovation (which is a massive undertaking and costs a fortune). Some of these beauties are open to the public and others operate as high-end inns, hotels, restaurants and spas. Following are a handful of favorites.
THE MOUNT Thoughtfully placed on a lovely swath of land with sweeping views, lie The Mount, Edith Wharton’s home and gardens. Having been beautifully restored, they are open to visitors in the summer and fall and available for events, such as weddings. The forested property has a variety of sculptures on exhibit.
BELLEFONTAINE MANSION This opulent “summer cottage” was constructed in the late 1890’s for socialite Giraud Foster and his wife. The design was inspired by Petit Trianon at Versaille and fitted with furnishings specially made in Paris. Canyon Ranch spa and health resort took over the restored mansion in 1989, one of only two locations in the country.
BLANTYRE Built in 1901, this beautiful estate was named for the owner’s mother’s ancestral home in Blantyre, Scotland. After the demise of the Gilded Age, Blantyre changed hands a few times before falling into the current hands of renowned designer Ken Fulk and investor/real estate developer Clark Lyda. Fulk is doing a top-to-toe renovation and plans to reopen mid-2024. I can not wait until the big reveal!
CRANWELL With a storied past, Cranwell is now a Miraval Spa and resort run by the Hyatt Corporation and known as Miraval Berkshires. The original mansion is now called by its original name, Wyndhurst Mansion, and boasts a gorgeous restaurant and rooms named for the writers, artists and creatives from the Gilded Age.
VENFORT HALL This Jacobean-style mansion was built for Sarah Morgan, the siter of J.P. Morgan, and her husband, George. It is still undergoing renovation, little by little, and is home of the Gilded Age Museum. A guided tour is a must for a wonderful insight to the Gilded Age! Ghost tours are available, as well as a variety of events and performances.
WHEATLEIGH This Italianate-style home was built in 1893 by Henry H. Cook and designed by Boston based architectural firm Peabody and Stearns. Wheatleigh is secluded and private, operates today as a luxury hotel. The elegant restaurant in the portico serves an elevated menu Wednesday through Sunday.
NORMAN ROCKWELL The artist who painted 322 covers for the Saturday Evening Post (322!!!) lived and worked in Stockbridge, in the Berkshires, from 1973 until his death in 1978 at the age of 84. Stockbridge epitomizes small town America, the ideal hometown for an artist who painted everyday scenes of life in America. The Norman Rockwell Museum is an absolute gem and I never leave the Berkshires without making a visit and paying homage to this great American artist.
CLARK ART INSTITUTE Sterling and Francine Clark were prolific art collectors who wished to establish a public art gallery to house their collection for the public to enjoy. After considering several locations (including Park Avenue in Manhattan) they settled on Williamstown, and the Clark Art Institute opened in 1955. This ranks as one of my top 3 museums in the entire country, a treasure trove indeed! Some favorite artists in the permanent collection include works by Winslow Homer, Alfred Stevens, Giovanni Boldini, Sir Lawrence Alma-Tadema, John Singer Sargent and Childe Hassam, in addition to a wonderful collection of works by Renoir, Degas, Cassatt and other greats. The temporary exhibits are always impressive.
Fumée d’ambre gris, 1880 (John Singer Sargent) and “Crossing the Street”, 1873-75 (Giovanni Boldini)
MASS MoCA (MASSACHUSETTS MUSEUM OF CONTEMPORARY ART) Vast is an understatement when trying to describe the venue of MASS MoCA. Set in 19th century mill buildings on 16 acres of Mohican ancestral homelands in North Adams, this is the largest contemporary museum in the entire country. The raw, industrial spaces and galleries are the coolest backdrop to the exhibits of modern visual and performance art.
CHESTERWOOD The historic home, studio and gardens of American sculptor Daniel Chester French (1850-1931), is set on 122 dreamy acres of woodland, gardens and meandering trails in Stockbridge. During his lifetime, French sculpted over 100 commemorative memorials and monuments for sites in the US as well as in Paris, many of which were created right here at his studio at Chesterwood. French is best known for his sculpture The Minute Man (Concord, MA) and his monumental statue of Abraham Lincoln (Lincoln Memorial, Washington, D.C.).
NAUMKEAG One of the Berkshires’ architectural gems and Gilded Age mansions, Naumkeag was built by New York attorney and US Ambassador to Great Britain, Joseph Choate, his wife Caroline (co-founder of Barnard College), and their only child, Mabel. Designed by the prominent architectural firm of McKim, Mead & White, the 44-room shingle-style home is strategically located on a hillside in Stockbridge, with views of the Housatonic River Valley. Mabel inherited Naumkeag in 1929 and spent the following 30 years creating the enchanting gardens with landscape architect, Fletcher Steele. Upon her passing in 1959 and without descendants, Mabel bequeathed Naumkeag in its entirety, with every piece of furniture and work of art intact, to The Trustees of Reservations. It is a time capsule and a living garden, which is enjoyed by 11,000 visitors each year.
SHAKESPEARE & COMPANY From 1978-2000 Shakespeare & Company was based at The Mount, the historic home of Edith Wharton, in Lenox. We were fortunate to live in Lenox during that period and attended a performance at The Mount. In 2000 relocated to its current home, also in Lenox.
BERKSHIRE OPERA FESTIVAL Relatively “new” to the scene, the Berkshire Opera Festival was established in 2016 and performs in theaters across the Berkshires
As a young adult, during my days off from work, I would drive along Route 7, stopping in at the plethora of antique shops that dotted the road. These particularly concentrated in Great Barrington and Sheffield, and they were plentiful. I was hoping to do the same on this recent trip and was dismayed that just a handful of stalwart shops remain, primarily in Sheffield. These are the long-timers, those with a stronghold in the industry and an even stronger passion for antiques.
I stopped in at Le Trianon Fine Art & Antiques in Sheffield, which retains an immense collection of museum quality antiques and paintings, including warehouses full. This reputable family business has traded in exceptional antiques and art for decades and sells to loyal collectors all over, including Ralph Lauren. The proprietor told me he predicts that antique shops will fizzle out in the next decade. “The younger generation is simply not interested,” he lamented.
Susan Silver Antiques set up shop in 1985 and specializes English and European antiques.
Linda Rosen Antiques is housed in a red barn and has more than 50 years of experiences dealing in Americana country antiques and art. I love the collection of primitive art and pottery.
Corner House Antiques has been in business since 1977, run by husband and wife Thomas and Kathleen Tetrol. The attractive gray barns holds their collection of antique wicker furniture dating from 1870-1930 and accessories. I can just imagine some of the wicker armchairs must have adorned the porches of mansions during the Gilded Age.
Kennedy Park, in Lenox, is a hardwood forest with old carriage roads and and 15 miles of trails for hiking and mountain biking. The lookout point offers a scenic view.
Whether you seek vistas, waterfall or backcountry trails, there are many places with fantastic hiking trails throughout the Berkshires. Monument Mountain (a 503-acre preserve in Great Barrington) boasts several beautiful trails, some of which involve scrambling up and over large rocks in order to get some glorious views.
The Hoosac Range Reserve in North Adams has some lovely hikes, include Sunset Rock Trail.
At 3,489′ Mount Greylock is the highest point in Massachusetts. Part of the Taconic Mountains, it is crisscrossed with trails and topped with the Veterans War Memorial tower, completed in 1932.
The Appalachian Trail traverses 90 miles through western Massachusetts, the entire length of the Berkshires. There are many places to access the trail and do day hikes.
I mentioned above the luxury spa resorts of Canyon Ranch and Miraval Berkshires. If you are more yoga-focused, the Kripalu Center for Yoga & Health in Lenox might be more your cup of tea (although not high end like the two spa resorts above). Established 50 years ago, Kripalu is a leader in yoga and mindfulness-based education. It offers a variety of programs, retreats and trainings, set on 125 acres with hiking trails and views overlooking scenic Stockbridge Bowl and the hills beyond.
Voila! A nice basket loaded with gilded apples in the Berkshires to enjoy when you are visiting this special part of New England! And if you would like to sample the fresh apples, be sure to visit the following the following:
Hilltop Orchards in Richmond is an extensive 100-year-old family-run property replete with apple orchards. They also produce their own cider (fresh pressed, sparkling and craft hard cider) at their in-house JMash Cidery, as well as their own wine under their brand Furnace Brook Winery. Enjoy their hiking trails in between cider and wine tasting and nibbling on freshly baked apple cider doughnuts. Their fresh pressed apple cider tastes just like autumn.
Founded and run by the Tawczynski family, Taft Farms in Great Barrington is a fantastic farm shop chock full of locally made treats, including preserves of all types, cheeses, baked goods and more. In the fall, they sell sorts of apple and pumpkin varieties are available, aw well as pressed apple cider and the yummiest apple cider doughnuts! I picked up a few jars of apple butter, apple jam and apple salsa for gifts (and to enjoy myself).
Also in Great Barrington, Windy Hill Farm has a self-pick apple orchard and an assortment of locally made items and hot cider in the shop.
November 22, 2023
The Loaded Trunk is a travel and lifestyle magazine founded by Jonna Robison, an interior designer with a deep curiosity and passion for traveling the world, connecting with artisans in different cultures and sourcing unique and beautiful objets d’art. Published seasonally, the magazine features a curated collection of travel, lifestyle, nature, art and design inspiration for a life well lived.