On autumn mornings in the Berkshires, cold air lingers in the valleys until the sun clears the ridges. By late morning, traffic is thick on the two-lane roads. People come up anyway, drawn by what the old money left standing when it ran out: barns, shuttered mills, marble churches and cottages the size of hotels. Those cottages came late to land that remains part of the Mohican homelands. In the 1730s, Mohicans established a community in what are now Stockbridge and West Stockbridge. Successive removals forced the Stockbridge-Mohicans to New York and then Wisconsin.
Improved rail links later brought wealthy families from New York and Boston. They imported a European model of country life, commissioning houses with formal approaches and gardens set against the woods, as “cottage” became a capacious euphemism. Each was designed around one family, along with the staff needed to sustain its summer life. When that domestic system broke down in the 20th century, the square footage remained, along with a Berkshire winter’s egregious heating bill. Some houses vanished. The survivors found new occupants and a job to do, which helped cover upkeep and brought once-private architecture within public reach.
For a fall weekend, the touristic appeal lies in the physical closeness of the region’s cultural mainstays to smaller places with notable histories of their own. This guide connects major collections and country-house gardens with businesses whose older ways of working remain useful. Restaurants and inns extend the experience into the evening, making the regional architecture part of a stay as well as something to admire. The route heads south from Williamstown, with reasons to linger in each town and a stretch of open country before the next stop.
An Insider’s Guide to the Berkshires
Inside the Bicentennial of Round Stone Barn
1843 West Housatonic St., Pittsfield, MA 01201
Hancock Shaker Village preserves the homes and workshops of a Christian community that held property in common and supported itself through farming and skilled trades. Now a museum and working farm, the village marks the Round Stone Barn’s 200th anniversary this year. Its circular plan took much of the awkward maneuvering out of dairy work. Wagons entered at the upper level and circled the central haymow, allowing drivers to unload without backing a team. One floor down, 52 cows faced inward to feed, while trapdoors carried manure to the cellar for later use in the gardens. Each floor opens directly onto the sloping ground, making the hillside as integral to the barn’s design as its circular footprint.
Hancock Round Barn.
Hancock Round Barn
Vanilla From Barrels That Never Empty
1 Center St., West Stockbridge, MA 01266
Every bottle of Charles H. Baldwin & Sons vanilla carries a trace of an earlier batch. Earl Baldwin Moffatt and his wife, Jackie, continue a family business founded in 1888 and based since 1912 in a former carriage shop beside West Stockbridge’s Williams River. The street-level shop sells the extract and baking supplies, while production depends on equipment passed down through the family. In a solid-copper percolator, Madagascar Bourbon beans steep in circulating alcohol and water for roughly six weeks before the extract moves into oak barrels that have been in continuous use since the 1920s. Two of the four barrels documented in 1923 remain at work. They are never fully emptied, so each fresh batch mingles with what came before.
225 South St., Williamstown, MA 01267
The Clark opened in Williamstown in 1955 to house Sterling and Francine Clark’s private art collection. Another collector is behind this year’s An Exquisite Eye: software entrepreneur and former museum trustee Aso O. Tavitian, whose foundation has given the Clark 331 works. The exhibition introduces roughly 150 of them, spanning about 1450 to 1850. Rubens and Vigée Le Brun share the galleries with Bernini. Madonna at the Fountain, a rare workshop replica credited to Jan Van Eyck and Workshop, measures just over 7 inches tall and under 5 inches wide. Architect Tadao Ando’s glass walls bring the surrounding hills into view, and meadow trails extend across the museum’s 140-acre campus.
Clark Art Institute.
Clark Art Institute
A New Palette at Garden Gables Hotel
135 Main St., Lenox, MA 01240
Garden Gables enters its first fall since a $1.5 million renovation of the Lenox house that began as Butternut Cottage in 1780. Behind the new interiors was some less photogenic work, including a new roof and plumbing. Boston-based designer Jessica Sullivan handled the visible changes, pairing black walls with dark timber and spreading oversize florals across a ceiling. The 16-room hotel reopened this spring on Main Street, with interiors adapted to the building’s existing proportions. Window placements and differing ceiling heights helped determine the individual rooms, whose layouts retain the irregularities of the old house.
Garden Gables Hotel.
Garden Gables Hotel
Dine on Farmhouse Pizza at Hilltown
224 Hillsdale Road, Egremont, MA 01258
Rafi Bildner’s pizza education took him from Berkshire pop-ups to Italy, where he traveled by bicycle to train with pizzaioli. Last fall, he opened Hilltown in the Egremont farmhouse that previously housed John Andrews Farmhouse Restaurant, continuing the dining legacy of a building dating back to the 1790s. Black-and-white photographs from his travels hang against forest-green walls, while a mural depicts the surrounding hills. Bildner calls his naturally leavened, “Neapolitan-ish” pies “pizza della terra,” or pizza of the land, with Berkshire producers contributing to the toppings. The Sweet & Spicy pairs soppressata with hot honey from Konkapot Apiary in Stockbridge, while the margherita uses mozzarella stretched in-house.
Hilltown Hot Pies.
Hilltown Hot Pies
Ventfort Hall Keeps the Repairs in View
104 Walker St., Lenox, MA 01240
When local preservationists entered Ventfort Hall in February 1997, ice covered much of the floor in its main rooms. A previous owner had already removed reception-room paneling in preparation for demolition. The 28,000-square-foot Lenox mansion had been built in 1893 for Sarah Morgan, J.P. Morgan’s sister, and her husband, George, who intended to spend their summers there. A century later, saving it meant figuring out how to put much of it back together. The preservation group bought the property that June, inheriting a puzzle of dismantled woodwork, most of it left on the premises. Outside, masons cleaned and reused the north wall’s original face bricks because no exact replacements could be found. Visitors now move through rooms at different stages of restoration, with the scale of the remaining work plain to see.
Ventfort Hall.
Ventfort Hall
Edith Wharton’s Garden Comes First
2 Plunkett St., Lenox, MA 01240
Edith Wharton was already writing about design when she built The Mount in Lenox in 1902. Her 1897 book The Decoration of Houses, co-written with architect Ogden Codman Jr., preceded the novels she would write here, including The House of Mirth. She approached the grounds with the same architectural discipline, arranging a sequence of outdoor rooms against the surrounding woods. The Lime Walk, lined with trained linden trees, connects the green-and-white Italian Garden to the French Flower Garden, while grass steps cut into the slope of the Rock Garden. Fall color spreads through the woods beyond these formal enclosures. Inside, Wharton’s attention to detail extends to the library shelves, where her penciled notes include corrections down to a single word.
The Mount.
The Mount
The Moving Floor at Chesterwood
4 Williamsville Road, Stockbridge, MA 01262
Daniel Chester French, sculptor of the Lincoln Memorial’s seated Abraham Lincoln, used Chesterwood as his summer home and studio in Stockbridge. His monumental figures needed to hold their proportions outdoors and from a distance, which presented a practical problem inside a workroom. The solution was a standard-gauge flatcar built into the studio floor. Assistants lifted adjoining panels and rolled a sculpture outside on tracks while French walked into the field to judge its silhouette. Architect Henry Bacon, his later collaborator on the Lincoln Memorial, designed the studio with 26-foot walls and abundant natural light. The finished marble Andromeda now dominates the room. In the residence, The Minute Man: Examining Patriotism, Victory, and Loss places French’s Revolutionary figure alongside historical and contemporary works considering military service and its human cost.
Chesterwood Residence.
Chesterwood Residence
Naumkeag’s Blue Steps After Dark
5 Prospect Hill Road, Stockbridge, MA 01262
October brings more than 1,500 jack-o’-lanterns into gardens once reserved for the Choate family. Naumkeag began as their summer retreat, a 44-room shingle-style house commissioned from McKim, Mead & White by New York attorney Joseph Choate and his wife, Caroline. Their daughter, Mabel, spent three decades working with landscape architect Fletcher Steele on the gardens, with Monument Mountain in the distance and the cobalt Blue Steps descending the hillside. She bequeathed the estate to the preservation nonprofit The Trustees in 1958. Today’s Pumpkin Show brings an evening crowd through those formerly private grounds, adding displays of mums and gourds along the garden paths.
Naumkeag Pumpkin Festival.
David R. Edgecomb
Dinner by Candlelight at the Old Inn on the Green
134 Hartsville-New Marlborough Road, New Marlborough, MA 01230
On New Marlborough’s village green, a stagecoach stop built in 1760 serves dinner in rooms lit entirely by candles. Iron chandeliers and wall sconces cast light across worn Windsor chairs and mahogany tavern tables, with a fireplace in each dining room. Chef-owner Peter Platt arrived in 2002 after 14 years leading the kitchen at Wheatleigh in Lenox. His cooking draws on French technique and longstanding relationships with local farmers and foragers, with a three-course prix fixe that changes with the season. The inn and neighboring Thayer House have 11 guest rooms between them, extending the building’s original purpose beyond dinner. Upstairs in Room 193, a copper vanity sits in the bath, while original paneling surrounds a working wood-burning fireplace.
Old Inn on the Green.
Jim Scherer