“Oronoque” // c1886

One of the most stunning and unique summer “cottages” in Stockbridge, Massachusetts has to be “Oronoque”, an eclectic Shingle-style home constructed of course ashlar blocks and shingle siding. The home was constructed around 1886 for Birdseye Blakeman, who lived in Stratford, CT. The home’s name is somewhat a mystery, but was possibly the name of his ancestral home in Connecticut. Just a few years after the homes completion, Blakeman died, and his widow continued to summer at the home until her death in 1912. The home was purchased by Norman H. Davis, a U.S. diplomat who later served as President Wilson‘s chief financial advisor at the Paris Peace Conference after WWI. Davis also served as Chairman of the American Red Cross, under three presidents. Under his direction, the Red Cross greatly expanded by thousands of volunteers and blood banks were established. The home was later owned by Boston University, who used it as lodging for students visiting the Tanglewood Festivals. It was later sold to a developer who appears to have converted it to a multi-family property.

“Highwood” // 1845

“Highwood”, was completed in 1845, and is likely credited to architect Richard M. Upjohn the son of Richard Upjohn Sr., who was known best for New York City’s Trinity Church, who was building a church for the Episcopal congregation in Stockbridge at the time. The home sits near Tanglewood, both since being absorbed into the Tanglewood Music Center campus today. The home was built for 27-year-old Samuel Gray Ward (1817-1907) an American poet, author, and minor member of the Transcendentalism movement. He was also a banker and a co-founder of the Metropolitan Museum of Art. Among his circle of contemporaries were poets and writers such as Ralph Waldo Emerson and Margaret Fuller. He desired country living with his family and became a “gentleman farmer” while he wrote in his home, overlooking the large lake. The family lived here year-round until he was called back to Boston to assist his father in business ventures. In 1857, the Wards realized their time at Highwood had come to an end and sold the estate to another Boston couple, William Story Bullard and his wife, Louisa Norton Bullard who settled into their new home, which they were not afraid to alter, including the addition of a mansard roof. The home was occupied by the family 1960. The home was later acquired by John Mason Harding, a New York lawyer and his wife, Mary Riker Harding. Idyllic summers did not last long for the Hardings as in the late 1970s, Tanglewood and the BSO sponsored rock concerts began playing. Mr. Harding complained that he didn’t expect to have Woodstock in his backyard and brought suit against the BSO to limit the length and noise level of the concerts. The home was eventually purchased by the BSO in 1986.

Mission House // c.1739

The Mission House, erected by the Reverend John Sergeant in 1739 on Prospect Hill in Stockbridge, Massachusetts, is an excellent and little-altered example of Georgian architecture as constructed on the New
England frontier. The home is a lasting remnant of early missionary efforts toward the local Mohican tribe. Reverend John Sergeant, the first missionary to the Housatonic Indians, moved to Stockbridge and preached to the native people here and at the Congregational Church. Sergeant and his wife Abigail moved to town, but she had made it clear that she wished to live on the hill, away from the village and the native people. Sergeant then built this home, a spacious and distinguished house for its frontier location. Though covered in part by a grant from the General Court, the cost of constructing such a house must have been a severe strain on Sergeant’s slender financial resources, as his salary at that time was 100 pounds per year. The home remained in the family until the 19th century. In 1928, long unoccupied and badly in need of repair, the house was purchased by Miss Mabel Choate, daughter of noted lawyer and former Ambassador to Great Britain, Joseph H. Choate. The house was taken down piece by piece, moved and reconstructed, on Main Street, in its current location. The Mission House was furnished with pieces appropriate to Sergeant’s economic status and his wife’s taste, many of them dating from the 1750’s or earlier. Since 1948, the home has been owned by the Trustees of Reservations.

Stockbridge Casino // 1887

The Stockbridge Casino was built in 1887-1888 according to the design of Stanford White, a principal architect of the firm McKim, Mead & White. The building was not what we think of casinos today, it was a ‘casino’ in the older sense of the term, having been established as a place for a reading-room, library, and social meetings, for the richest in town to hang out. For forty years, it offered its members tennis, billiards, dances, theatricals, and lectures throughout the summer seasons. After a period of decline after WWI, the group sold the property to Mabel Choate, who wished to move the Mission House (home of the first missionary to the Stockbridge Indians) from up on Prospect Hill to Main Street. There was reluctance to see the casino torn down, so a group of local citizens — led by Walter Leighton Clark, President of the Grand Central Art Galleries of New York; Austen Fox Riggs, psychiatrist; and Daniel Chester French, sculptor — acquired land at the end of Main Street and moved the Casino to its present site, saving it from the wrecking ball. The building was renovated and reopened in 1928 as the Berkshire Playhouse, and was later renamed the Fitzpatrick Main Stage, a theater run by the Berkshire Theatre Group.

Citizen’s Hall // 1870

Citizens Hall, which was built in 1870 in a small village within Stockbridge, MA, is a small-scale version of the civic buildings constructed in the Second Empire in American towns and cities following the Civil War. The building is the architectural epicenter of Curtisville (now sometimes referred to as Interlaken), a small community within the Town of Stockbridge, which grew up around twelve mills. The mills are gone but several significant structures remain, also retaining their rural character. Citizens Hall was designed by Charles T. Rathbun, and inside, the two rooms on the first floor housed the public school and the second floor was the community assembly hall. The building was threatened with deferred maintenance in the mid-20th century and its future was uncertain until 1975 when a local group worked with the State Historic Preservation Office and acquired a grant to make needed repairs on the building. Today, the structure is maintained and houses the Art School of Berkshire (now known as Interlaken School of Art). Look at that historically appropriate paint scheme!

Elm Court // 1886

Real estate listing 11-2020

At 55,000 square feet and 106 rooms, the Elm Court mansion retains the title of the largest American Shingle Style home in the United States. The structure was built for William Douglas Sloane and Emily Thorn Vanderbilt (granddaughter of Cornelius Vanderbilt) as their summer “cottage” in the Berkshires. The home straddles the towns of Stockbridge and Lenox and sits on a massive parcel of land, giving the owners space to breathe the clean countryside air. Emily’s brother, George, built The Biltmore in Asheville, North Carolina and her sister, Eliza (Lila), constructed Shelburne Farms in Shelburne, Vermont. The home was constructed in 1886 from plans by the great Peabody & Stearns architects. Shortly after the turn of the century, ca. 1901, the couple commissioned Peabody and Stearns again, to vastly enlarge their original house. The additions used both Shingle Style and Tudor Revival motifs, and the result is a structure highly reminiscent of an English country house. William Sloane died in 1915, and Emily Vanderbilt continued to use the summer cottage, and in 1921, she married a summertime neighbor, Henry White, a career diplomat. While Henry White died in 1927, Emily retained the house and kept the grounds running until her death in 1946. The property’s use evolved into an inn in the late 1940s. During the 1950s, it embraced the public for dinners, overnight accommodations and events. Eventually Elm Court’s doors closed, and for approximately 50 years the mansion succumbed to significant theft and vandalism. The property has been listed for sale numerous times in the past decades, after a renovation by the last owners in the Sloane family. It is now listed for $12,500,000!

St. Paul’s Church, Stockbridge // 1884

Located on the idyllic Main Street in Stockbridge, MA in the Berkshires, this stone church marks the emergence of the once sleepy town into a summer retreat for wealthy citizens, escaping the cities in the late 19th century. This building is Charles Follen McKim’s first church design, a building reflecting his early training in the office of H. H. Richardson with the use of Romanesque detailing, though with a hint of Norman design. St. Paul’s Church is constructed of gray Berkshire granite with stained glass windows by John La Farge. The church replaced an older wooden church building designed by Richard Upjohn in the Gothic Revival style. The church was almost entirely funded by Charles Butler, a New York lawyer who wanted to honor his late wife Susan Ridley Sedgwick Butler, a descendant of Theodore Sedgwick, whose home I featured not long ago.

Red Lion Inn // 1897

The largest building on Main Street in Stockbridge has to be the Red Lion Inn, a regional institution and one of the best places to rest your head in New England. The inn got its start just before the Revolutionary War. According to tradition, Silas Pepoon established a small tavern on the corner of Main Street in 1773, under the sign of a red lion. A year later, angry citizens gathered at the tavern to boycott English goods and to pass resolutions protesting the oppressive Acts of Intolerance levied against the colonies. Since its earliest days, the inn was a vital gathering place for locals and has continued to play an important role in the life of the community ever since. In 1862, the inn was owned by Mr. and Mrs. Charles Plumb, avid collectors of rare and fine items, who became renowned for their impressive compilation of colonial antiques. A fire in 1896 destroyed the building but its remarkable array of collectibles was saved and the inn was rebuilt within a year by designs from Harry E. Weeks, a Pittsfield-based architect.

Sedgwick House // 1785

Built in 1785, the Sedgwick House on Main Street in Stockbridge, MA, is the oldest of several Federal mansions built in town after the Revolution. Theodore Sedgwick (1746-1813), one of the early lawyers of Berkshire County, moved to Stockbridge in 1785 and built this house. From 1796 to 1799 he was a Senator in the federal government, and declined a position of Secretary of the Treasury offered by George Washington. Before this, when a House Representative, he was nominated the fourth Speaker of the House. An ardent Federalist, Theodore retired from the national arena upon Thomas Jefferson’s election. Sedgwick was also a member of an early abolitionist society organized in Pennsylvania in 1775 and played a key role in abolishing slavery in Massachusetts by his win in the case of Bett v. Ashley. In this case, Sedgwick served as attorney of Mum Bet (also known as Elizabeth Freeman) an enslaved woman in nearby Sheffield and argued that slavery was inconsistent with the 1780 Massachusetts State Constitution, and won. Bet became the first enslaved African American to file and win a freedom suit in Massachusetts, effectively abolishing slavery in the state. She was later buried in the Sedgwick Family burial plot in Stockbridge. The home was later owned and occupied by Catharine Maria Sedgwick, Theodore’s daughter, who became one of nineteenth-century America’s most prolific women writers. She published six novels, two biographies, eight works for children, novellas, over 100 pieces of short prose and other works.

Guerrieri Block // 1921

Norman Rockwell‘s ‘Home for Christmas’ painting in 1967 depicts the Main Street scene in Stockbridge, Massachusetts, and epitomizes the essence of Christmas in small towns across the country. In the iconic painting, you can find many landmarks (including the Town Offices building) that make up the quaint main street, that typifies many small New England towns. At the center of his painting, the Guerrieri Block can be seen with a Christmas tree lit up in the window on the second floor. The Guerrieri Block was built in 1921 by Antonio Guerrieri, a skilled woodworker who sold and repaired antiques in one of three street level shops in the block. He and his family lived in an apartment on the second floor. The next year he completed construction of a shop behind the block where he worked out of. In 1953, Norman Rockwell moved to Stockbridge and spoke with Antonio about using the second floor of his building as a studio. Antonio constructed a large central bay window with plate glass to flood the space with light and allow Rockwell to work while observing the street below. Rockwell used the space as his studio until 1957. The building has since been occupied as a general store.