Since 1953
The Highfield story
Highfield Club was founded in 1953 by a group of families who wanted a family club. The clubhouse is the former Dr. Edgar Stillman estate, designed by architect Theodate Pope Riddle, and the grounds cover more than 600 acres above Lake Quassapaug.
The club
A small family country club
A private nine-hole course with multiple tee boxes, a full-service golf shop and driving range, a junior golf program, platform tennis, pickleball, the pool and Cliffside — the club's private Lake Quassapaug property. The club and the golf shop welcome members and their guests all season.
Become a memberHighfield in numbers
Holes
9
Acres
600+
Founded
1953
Our history
The club through the years
1953
The club is founded
Founding families establish Highfield on the Stillman estate in Middlebury.
1950s
The course
Nine holes with multiple tee boxes: 6,600 yards, par 72, slope 136 from the championship tees over two loops; 5,700 yards from the ladies' tees.
2000s
Racquets and the pool
Platform tennis, pickleball and the pool round out the summer and the winter season.
Today
Three generations
Founders, children and grandchildren are still members. The seven-week summer day camp welcomes children aged 4 to 15.
Contact
Who to call
The clubhouse handles membership and events; the golf shop handles tee times, the league and the shop.
Clubhouse
(203) 758-9101 · membership, weddings and private events
Golf shop
(203) 598-3815 · tee times, guest fees, men's league
Summer day camp
Seven weeks, ages 4–15 · register through the clubhouse
Interested in joining?
Membership categories for residents, juniors under 35 and non-residents.
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