Tanglewood // c.1865

The 200-acre campus of Tanglewood, where the Boston Symphony Orchestra spends its summer months, spreads the grounds of two historic summer cottages in the charming town of Stockbridge, MA. One of the summer “cottages” Tanglewood, where the music center gets its name, was constructed around 1865 for Caroline Sturgis Tappan, husband William Aspinwall Tappan and their two daughters, Ellen Sturgis Tappan and Mary Aspinwall Tappan. Mary, with her niece Rosamund Hepburn, donated the family summer home, Tanglewood in 1937 to Serge Koussevitzky, a Russian-born conductor, composer and music director of the Boston Symphony Orchestra from 1924 to 1949. The campus has since grown astronomically as it hosts musicians and tourists from all over the region and globally to experience the arts in the charming town in the Berkshires. The Tanglewood house retains much of its historic architecture and siting, overlooking the Stockbridge Bowl (lake).

Chesterwood // 1901

Chesterwood is the former summer home, studio and gardens of American sculptor Daniel Chester French (1850–1931), who is best known for creating two of our nation’s most powerful symbols: the Minute Man (1871–75) at the Old North Bridge in Concord, Massachusetts, John Harvard in Harvard Yard, and Abraham Lincoln (1911–22) for the Lincoln Memorial in Washington, D.C. Daniel Chester French was one of the most successful artists of the late 19th and early 20th centuries, producing more than 100 works of public sculpture. In the fall of 1895, he and his wife drove by horse and buggy and discovered the resort town of Stockbridge. They returned the next summer and purchased the Marshall Warner farm from the family who had purchased the land from Mohican Native Americans. The French family and two maids moved into the white clapboard farmhouse the next summer. To ensure that his summer would be productive as well as restful, he improvised a studio in the barn. He asked his friend and colleague, architect Henry Bacon, to design a studio for him (Bacon would later work with French on the Lincoln Memorial). Soon, in spite of renovation, the original farmhouse was deemed inadequate and French commissioned Bacon to design a residence, completed in 1901. The family owned the home for decades, even after Daniel Chester French’s death. Much of the credit for Chesterwood’s preservation and metamorphosis from summer retreat to public site belongs to Margaret French Cresson (1889–1973), the sculptor’s daughter. After her parents’ death, she maintained the property and began to use it year-round, assembled the work of her father, and established the estate as a historic site of the National Trust for Historic Preservation.

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.

Merwin House // 1825

In about 1825, Francis and Clarissa Dresser built this charming brick Federal house in the rural town of Stockbridge, MA. Just 25 years later, the railroad arrived to town, connecting it to Connecticut and New York to the south, opening the town up as a leisure destination for wealthy city dwellers looking to escape the noise and congestion of the city. The period following the Civil War through World War I saw the Gilded Age reach the Berkshires. With artists, writers, financiers, and industrialists flocking to the rural hills of western Massachusetts for seasonal escapes. In 1875, William and Elizabeth Doane, wealthy New Yorkers, purchased Merwin House from the Dresser family to use as a summer retreat. As the Doane family grew to include two young daughters, Vipont and Elizabeth, they added a Shingle Style side addition to the original brick structure. The home became known as “Tranquility”, even after the home was willed to daughter Vipont. After a couple marriages, Vipont married Edward Payson Merwin, a New York stockbroker. Historic New England acquired Merwin House in 1966, shortly after the death of Marie Vipont deRiviere Doane Merwin, known as Vipont. It was her desire to leave Merwin House as a museum, as her will states, “as an example of an American culture which is fast becoming extinct.” The space is occasionally open for tours and is partially occupied by the Housatonic Valley Association.

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.

Children’s Chimes Tower // 1878

Located in front of the old Town Hall and Congregational Church in Stockbridge, this tall carillon (bell tower), was gifted to the town by David Dudley Field, Jr. in memory of his grandchildren. His one condition was the chimes were to be rung everyday at 5:30 p.m. between, “apple blossom time and the first frost on the pumpkin”. The tower has a stone base and wooden belfry surmounted by a pyramidal roof with clocks on all four sides. The tower remains a gift, not only to the memory of his grandchildren, but to passersby who are lucky enough to hear the bells toll.

Thomas Carter House // 1830

All I want for Christmas is a brick Federal house! This home in Stockbridge, Massachusetts was constructed in 1830 by Thomas Carter (1777-1863) and his wife Anna. The couple farmed the property and had eleven children (plus two who died in childbirth). According to a family history, the lime for the mortar on the home was burned in a kiln on the property by Thomas. The ancestral home remained in the family for generations, including by John Calvin Calhoun Carter, a town selectman, who added a full-length porch on the home in the mid-late 19th century (since removed). The home’s rural charm remains even-though it sits on a busy road in the Berkshires.

First Stockbridge Town Hall // 1840

The Town of Stockbridge, MA was incorporated on June 22, 1739. After that time the town held meetings and conducted business in the First Congregational Meeting House until 1840 when this Greek Revival town hall building was erected on the church’s property as a gift. A stipulation was made that if the Town government constructed or moved to a new town hall building, the property ownership would revert to the Church. The town outgrew the building and constructed a new building toward the center of town, but named it Town Offices, a cheeky way to retain ownership of this building. Eventually, that building too was outgrown, and the town hired Pittsfield-based architect Harry E. Weeks to modify and enlarge the building in 1903, in the Neo-Classical style to compliment the original Greek detailing. As expected, the town moved again in the 2000s to a former school, on Main Street, but again retained the building.