by Anne Motto, F.M. Kirby Curator of Collections
June 2, 2026
For part one of this story, see Cherrycroft, Part 1: Mansion for Sale
Upon their first summer renting in Morristown, Mr. and Mrs. Dudley Olcott II purchased “Cherrycroft,” the Normandy Park estate of recently widowed Mrs. Thomas Pinckney. Like many of their Gilded Age neighbors, the Olcotts primarily occupied their new home for the spring and fall seasons and quickly became enmeshed in the town’s high society. Along with membership in the area’s exclusive social clubs, including the Morris County Golf Club and Whippany River Club, the Olcotts soon opened their white colonial mansion to their guests, entertaining to great acclaim and touching off the home’s colorful history.
Five years after their arrival, in the fall of 1909, the couple extensively remodeled the home, adding a new Italian garden designed by noted landscape architect Ferrucio Vitale that would be lauded in national publications. Described by one author as “a sea of flowers, possibly unequalled in its profusion of bloom,” the gardens at Cherrycroft were surrounded by high brick walls that encircled pools, arbors full of roses, terraces, and “intimate paths.” Said to be Italian in its architecture and English in its plantings, the garden was noted for its romance, making it the perfect setting for the dazzling soirees the Olcotts soon held.
The pinnacle of the couple’s social career in Morristown came on June 24, 1911 when they hosted a burlesque that “surpassed anything in the way of social functions.” The party garnered widespread attention, and even the New York Times reported on the affair noting that “their Normandie Park home and grounds were brilliant with electric lights and Japanese lanterns while the Italian garden was attractively decorated.” More than 300 masked guests were in attendance with guests faces revealed at midnight as dinner was served.
When not hosting parties at Cherrycroft, the Olcotts spent their summers at Bar Harbor or their cottage in Southampton. Sometimes remaining behind in Morristown, Mr. Olcott also on more than one occasion preferred to summer alone in Europe. This was perhaps a harbinger of things to come, as in 1932, Mr. and Mrs. Dudley Olcott II became national news when he traveled to Reno to obtain a divorce on the grounds of desertion. Not “deserted” for long, Mr. Olcott remarried hours after he was awarded the divorce, while Mrs. Olcott married her third husband, a Russian prince, just three months later in Paris. Meanwhile, the former couple’s beautiful home in Morristown was leased for the reputed price of $30,000 per year (~$537,000 today) and later sold to media mogul Eugene V. Brewster. Under its new owner, Cherrycroft would go on to become the scene of a Hollywood scandal that created an even greater spectacle than the Olcotts’ soirees.
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