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Highfield Club

Location icon 256 White Deer Rock Rd, Middlebury, CT
Phone icon (203) 758-9101
9

Holes

36

Par

3,253

Yards

36.6

Rating

125

Slope

Unknown

Driving Range

Description

Highfield Club in Middlebury is a private club with a traditional 18-hole layout and a calm, tucked-away feel once you’re on property. The course plays through classic Connecticut terrain—tree-lined corridors, subtle elevation movement, and holes that reward measured placement over all-out aggression. It’s the kind of routing where the “safe miss” matters, especially on approach shots into greens that can be more protected than they look from the fairway. The club culture is typically member-focused and community-driven, with leagues and events that keep the season active without feeling overly formal. If you’re looking for an understated private club with enjoyable, repeatable golf in western Connecticut, Highfield fits that profile well.

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Hidden gem with a colonial feel but this country club has all the amenities. Attending a special occasion in a room held by a club member for private dinners , the Highfield Club was a fine discovery. The atmosphere with the wood burning fireplace, autumnal decorations and table setting was something I don't see enough of anymore. Service was attentive and polite. All of the food was perfectly made, from the Caesar salad to all three mains guests could choose from before attending. My filet mignon was if not the best I've ever had, definitely in the top five. Incredible. Our wait staff told us Highfield cooks them medium unless a guest specifies a preference. A few of asked for medium rare. Cooked perfectly, even leaning rare which we all enjoyed. The demi-glace served with the filets was perfect and only added to this culinary experience.

Juliana

5

over 3 years ago

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I’ve visited Highfield Country Club a few times as a guest over the past few months and wanted to share some feedback. While the location is beautiful, I’ve experienced service issues that were disappointing for a club of this caliber.During several visits, I noticed concerning behavior from a few staff members. Two female employees early to mid 20's (one brunette, one blonde) seemed unprofessional in their interactions, which at times felt dismissive or undermining. Additionally, an older male employee with tattoos and a beard probably in his mid 30's appeared disengaged while performing his duties and spoke to me in a condescending manner, as if he did not want to be there and it honestly made me very uncomfortable. These experiences made my visits less enjoyable.I hope management uses this feedback to review staff training and supervision. With more attention to professionalism and customer service, Highfield Country Club has the potential to fully live up to its reputation.

Svol

2

6 months ago

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An incredibly special place. We are privileged to be members here and enjoy spending as much time as we can at Highfield. As a small membership club

Raj

5

almost 4 years ago

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A hidden gem. Beautiful, challenging course,, family friendly club with pool, tennis, pickleball, fantastic clubhouse and fantastic lake access.

Charlie

5

over 4 years ago

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Picturesque and secluded country club and 9-hole golf course on an old estate nestled up in the woods in Middlebury. The golf course is challenging and Bill the pro is super nice and very competent. The tennis courts are in good condition and the pro Richard is very nice and fantastic for lessons. The food is always good quality and tasty. Love the quietness of the pool. The summer camp is great for younger children up to age 9.

Donna

4

almost 10 years ago

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Morning 8 AM - 11 AM
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