Since 1919, Winchester Country Club has hosted seven Massachusetts Amateur championships and two state opens in addition to other state and regional tournaments. However, its best-known contribution to Massachusetts golf is its annual father & son tournament, the longest-running such event in the country. First held in 1919, as sons and fathers returned from World War I, and the invitational tournament quickly became a mainstay in Massachusetts golf.

Today, Winchester Country Club remains one of the premier courses in the state. Featuring views of both the Mystic Lakes and the Boston skyline. The club is set to undergo a course-wide renovation of the golf course starting on Aug. 3rd with golf course architect Andrew Green. Upon completion in the fall of 2026, the work will continue to provide both a challenge and enjoyment for its members and their guests. Winchester CC will also be hosting the Massachusetts Amateur in July of 2026.

Position:

Do you like to be outside? Do you enjoy the game of golf? Do you like to exercise and stay in shape? You can come to the right place! The Greenskeeper position offers all these things and more!

The Greenskeeper position plays a vital role in the maintenance and upkeep of such a remarkable golf course. The Greenkeepers are an integral part of the operation and provide the high-level golf course conditioning the members come to expect.

Tasks include:

Mowing Greens, Tees, Approaches, Fairways, Roughs, Clubhouse Grounds. Keeping bunkers pristine and playable through proper raking techniques. Divot repair on tees and fairways. Debris removal on surfaces and cart-paths. Summer rotary mowing and string trimming, Fall leaf clean-up, and small improvement projects to the golf course in the shoulder seasons are all tasks that will encompass the position. The maintenance and preparations of the driving range, practice greens and short game playing areas, to name a few!

Qualifications:

We are looking for energetic and enthusiastic individuals with a positive attitude to be a part of a great team culture, working alongside a passionate crew to achieve outstanding results, and presenting an amazing golfing experience for the members and their guests.

Positions Available:

As early as March 2026 through November 2026. Employment will start back up in Mar/Apr 2027.

** start time may change on days for special events, holidays, weather & seasonal sunlight **

• Must be able to carry and lift up to 50 lbs at a time.
• The job requires one to be on their feet for most of the day.

Starting wages: $18-$19.00/hr

The hiring range represents what Winchester Country Club reasonably expects to pay for this position at the time of posting. The actual wages offered will depend on the selected candidate’s qualifications, experience, skills, and other job-related factors.

Benefits:

Lunch provided, uniforms, golfing privileges and having fun! So what do you say?!