MIDDLEBURY, CONNECTICUT
A family club since 1953
Highfield Club is a small, private family country club set on more than 600 acres in Middlebury: a nine-hole course with multiple tee boxes, a full-service golf shop and driving range, platform tennis, pickleball and a clubhouse in the former Dr. Edgar Stillman estate.
Our history
Seventy years of family golf
1953
The club is founded
A group of families who wanted a club of their own found Highfield on the former Stillman estate.
1950s
Nine holes open
The course opens with multiple tee boxes: 6,600 yards and a 136 slope from the championship tees over two loops.
2000s
Platform tennis and pickleball
Two heated, lit platform tennis courts and two pickleball courts join the golf course and the pool.
Today
Three generations of members
Original founders, their children and grandchildren still play here. Junior golf and the summer day camp keep the next generation on the course.
"A club where everybody knows your name — the course is in beautiful shape and a nine-hole loop after work is the best part of the week."
A Resident Family member
Gallery
Interested in joining?
New members join as Provisional Members for one year with full privileges.
Membership informationContact
Phone
(203) 598-3815
highfield@golfbooker.app
Address
256 White Deer Rock Rd
Opening hours
Golf shop daily 7:00–19:00 · Clubhouse 11:00–21:00
© 2026 Highfield Club. All rights reserved.
A private family club since 1953