Highfield - A Club With a Unique History

Over ninety revelers celebrated the 100th birthday of the Highfield house during a festive event at Highfield, a family-oriented country club in Middlebury. “The Club has such a unique house and property; we needed to celebrate its history,” commented one Club member.

The Highfield house is a historic building located in Middlebury, Connecticut. The House, surrounded by over 600 acres of land was the former estate of Joseph and Elizabeth Chamberlain. Commissioned to build the Chamberlain estate, Theodate Pope Riddle, one of the first female architects, built a comfortable English Arts and Crafts style cottage on a hill above Lake Quassapaug. Theodate Pope Riddle also designed what is now the Hill-Stead Museum (1898), Westover School (1906-1909), and Avon Old Farms School (1918-1927). In 1915, she was one of 763 survivors of the RMS Lusitania; torpedoed and sunk by a German submarine.

In 1953 the Highfield estate was purchased by a group of families dedicated to establishing a club for the whole family. A club where men and women could play golf and tennis and children could swim and play. Minor interior changes were made to convert the house into a clubhouse, and Orrin E. Smith and Al Zikorus maintained the property’s natural beauty when designing a nine-hole golf course. Today, Highfield maintains the family atmosphere envisioned by its original founding families.

Highfield is a year-round club offering amenities for golf, tennis, swimming, lakeside activities (cooking out, kayaking, swimming, and sailing), dining, paddle tennis, pickleball and an amazing summer camp. Highfield remains a club for all ages.