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The Ashley House, Sheffield MA
An Upper Housatonic Valley African American Heritage Trail anchor site, this 1735 house was home to Col. John Ashley, who petitioned against British tyranny. In 1781, Mum Bett, an enslaved African American in the Ashley household, took a stand for her freedom, which helped end slavery in Massachusetts.
The Folly at Field Farm, Williamstown MA
Set in a stunning natural landscape and surrounded by sculptures, gardens, and hiking trails, the Folly and Field Farm epitomizes the Modern Movement. Tour the award-winning Folly – all curves and shingles – designed in 1965 by Ulrich Franzen.
The Mission House, Stockbridge MA
John Sergeant, first missionary to the Stockbridge Mohican Indians, built this house c. 1740. Restored on its present site in 1928, this National Historic Landmark contains a fine collection of period furnishings and features a Fletcher Steele–Colonial Revival garden.
Naumkeag, Stockbridge MA
For generations of the Choate family, Naumkeag, a National Historic Landmark, was a refuge of beauty and respite. McKim, Mead & White designed the house in 1885, and it still contains all of its original furnishings. The famous gardens, designed by Fletcher Steele, frame lovely views of the Berkshire Hills.
The William Cullen Bryant Homestead, Cummington MA
With views of the Westfield River Valley, hiking trails, a historic red barn, and a rambling summer villa, this National Historic Landmark is located in the heart of the Highlands. In 1865, Bryant, a famous poet and newspaper editor, converted his boyhood home into a summer refuge.
Eleanor Cabot Bradley Estate, Canton MA
A colonial farmstead-turned-country–estate, this well-designed mix of formal gardens, fields, and woodlands can be explored along 3 miles of trails. The elegant main house is a popular venue for weddings and other celebratory events.
The Old Manse, Concord MA
A National Historic Landmark built just before the Revolutionary War by Ralph Waldo Emerson’s grandfather, the Manse has witnessed early America’s political and literary revolutions. Minutemen and Redcoats fought the Battle of Concord in nearby fields and woods.
Great House at Castle Hill, The Crane Estate, Ipswich MA
A David Adler masterpiece, this elegant country house provided a gracious summer home for the Crane family of Chicago. Tour lavishly furnished rooms and enjoy panoramic ocean views. Also, explore spectacular grounds designed by the Olmsted Bros and Arthur Shurcliff. A National Historic Landmark.
Paine House at Greenwood Farm, Ipswich MA
Dating back more than 350 years, this former saltwater hay farm offers spectacular views of marshlands and coastal islands. Its centerpiece is the Paine House (1694), a fine example of First Period design and craftsmanship. The furnishings reflect a summer home of the Colonial Revival Period.
The Stevens-Coolidge Place, North Andover MA
This 18th-century farm evolved into an early 20th-century country estate for diplomat John Gardner Coolidge and his wife, Helen Stevens Coolidge. The house and gardens boast some of the finest work of Colonial Revival architect Joseph E. Chandler.