The property containing Hampton Terrace originally was the site of Lenox's blacksmith. In 1852, Edmund Spencer built a home on the property. It was acquired in 1867 by the widow of Ogden Hoffman, "one of the most eloquent lawyers New York ever contained." Colonel and Mrs. R S. Oliver of Albany acquired it in 1873.

In 1896, Philadelphia marble dealer John Struthers and his wife Virginia Bird purchased the house, as it was next door to the summer home of their Philadelphia friends, the Whartons - parents-in-law of author Edith Wharton. Their aim was to replace it with a "cottage" suitable to the social strata they had achieved. According to a February 24, 1897 article under the banner THIS WEEK IN LENOX, "The frame to Struthers cottage has arrived at the train station from New Haven and work can now accelerate." The Struthers, who were concurrently building their "winter home" at the exclusive Jekyll Island Club in Georgia, named their new summer home "Wynnstay." It originally had eleven bedrooms, two bathrooms and a stable on the property. They visited each summer until 1919.

Edith Wharton lived next door to the Struthers for three years and down the street for another ten. She featured Mrs. Struthers prominently in "The Age of Innocence." According to the novel, Mrs. Struthers held parties in her home, derisively dubbed "French Sundays" - which meant she allowed drinking and smoking and entertained "actresses." To the stiff New York Gilded Age crowd at the turn of the century, this behavior by someone from Philadelphia was blasphemous - although many in their group reveled at their inclusion in this "naughty" social circle. Ironically, the Struthers sold Hampton Terrace in 1919 to the absolute cream of New York society.

The house was bought by Robert E. (Ed) Bonner, Jr. His father was the classic story of an Irish immigrant with $5 in his pocket. Bonner founded the New York Ledger, built a newspaper empire, and became one of the richest men in the country, traveling in the same circles as the Vanderbilts. Ed, Jr. took over the paper and married Kate d'Anterroches Griffith, great, great granddaughter of General Lafayette. They were both very social in New York and Europe, owned a number of race horses, and spent half of each year in Paris. Ed built his primary home on the corner of Madison Avenue and 53rd in New York City, but he and "Kitty" spent their summers in Lenox for 20 years. They renamed their summer cottage "Hampton Terrace" after Hampton, one of their four children.

Kitty d'A Bonner was a centerpiece of Lenox's social elite and a member of the exclusive Lenox Club, located two doors up the street. She had a "Hampton Terrace" logo designed in Paris in 1928, which is featured on this website.

The Bonners sold Hampton Terrace to Carl Giese in 1937 and Hampton Terrace's legacy as a guest house and inn began at this point. Carl's son remembers erecting the sign post which is still standing 62 years later. The Gieses passed Hampton Terrace on to Bertha Trombly in 1945. Her 1948 brochure touts the 6 weeks of daily concerts at the Tanglewood Music Festival and explains "Breakfast only is served. There are excellent eating places nearby." Some things have not changed in half a century.

Hampton Terrace owners did change, however. After six years the Tromblys sold to the Stachs and sixteen years later, the O'Brien's, who ran the bed & breakfast for 31 years and raised six children on the property.