Golf Staycation Trip 7: The Perfect Parent's Golf Day - MASSGOLF


A busy July may have delayed Golf Staycation Trip #7, but as they say, good things come to those who wait. In this most recent excursion, we discovered the perfect parent’s golf day. Human parents, dog parents, grandparents, any kind of parents…this golf day is for you.

Trip #7 – The Perfect Parent’s Golf Day (By: Stephen Hanjack)

Cyprian Keyes Golf Club (Boylston, MA)

As you probably know by now, a Massachusetts Golf Staycation, as we define it, is taking a vacation day to explore and experience golf here in the Commonwealth. Some of our past trips have included early alarms, hundreds of miles of travel, and overnight stays. But not this time.

This time, I (selfishly) wanted to find the perfect way to enjoy a Golf Staycation, while still fulfilling parental duties. Doing this obviously brought restrictions and limitations into play, but navigating these itinerary-bunkers is half the fun anyways. When it was all said and done, Cyprian Keyes GC proved to be the perfect venue for this Dad Day.

The closing hole at Cyprian Keyes GC offers a beautiful view and one last chance at birdie.


I have found that planning a Golf Staycation can be just as enjoyable as playing it. And with several different Golf Staycation trips under my belt, I have identified a 5-step process that you might find helpful in creating your perfect golf day.

  • Step 1 – Check the 10-day forecast: Know what type of weather you are comfortable playing in and what day(s) of the week you can take off.
  • Step 2 – Lay out your hourly timeline: With drop-off at 8 a.m. and pickup at 4:30 p.m., I estimated 7.5 or 8 hours of playable golf time.
  • Step 3 – Start digging: For this trip I had two ideas in mind. Play every hole at one of the 36-hole facilities in the area or play 27-holes, mixing a 9-hole course with an 18-holer.
  • Step 4 – Drive time & play time: With neither of the local 36-hole venues having available tee times on their two different courses, I settled in on a 27-hole day. When I realized Cyprian Keyes GC offered both a 9-hole par-3 course and an 18-hole championship course, my search was over. Available tee times with NO midday drive…say no more.
  • Step 5 – Lock it in: If you haven’t noticed, tee times disappear pretty quickly these days.

The Par-3 Course | Cyprian Keyes GC

With my day now planned out, I was excited about the prospect of settling in with a nice warm-up round on the par-3 course before taking on the championship track at Cyprian Keyes GC.

The fun-named 2nd hole on the par-3 course at Cyprian Keyes.

Anyone familiar with golf travel knows that par-3 courses are being added at almost every major golf destination in America. These places like Pinehurst Resort are not half-heartedly creating par-3 courses either, they are bringing in the biggest names in golf to do so. Pebble Beach was so serious about their short course that they employed Tiger Woods to handle the re-design of it.

Cyprian Keyes was ahead of the Pinehurst’s of the world. They unveiled the par-3 course as part of the facility’s original design which opened in 1997. In speaking with General Manager David Frem, he indicated that last year’s surge in golf helped Cyprian DOUBLE the rounds played on the short course vs. 2019. And if my visit was any indication, it looked like the popularity is still there. The par-3 seemed to be buzzing with activity throughout the day. With holes ranging from 85-165 yards, it certainly tests several different clubs in the bag. And with fun hole names like “Munchkin” it tough not to keep a smile on your face throughout.

Getting to take some meaningful swings while also familiarizing myself with the turf and green conditions was a nice bonus. I was able to hit 7 different clubs off the tee, which was a perfect way to tune-up for the big course. And who doesn’t love 9 extra opportunities to make an ace?!

The Championship Course | Cyprian Keyes GC

I won’t hit you with a hole-by-hole breakdown of Cyprian Keyes, I’ll let you go experience it for yourself. But there were a few things that really stood out from my trip, like my foursome. Craig, Mike and Mike were friendly and welcoming from the start, and their competitive banter made me wish I was part of their match. As I reflect on my experience, I struggle to find better words to describe Cyprian than what I had scratched in my notebook: a proper test in course management and patience. Originally, I hesitated to use those words as I feared they would indicate too many forced layups, which is not the case.

What I found is that the course often asks you; Can you hit this shot? And is it worth the risk? If you have your A-Game off the tee, there are corners to be cut and speed-slots to be found. If you’re not feeling so hot off the tee, there are plenty other options the course gives you. Instead of taking on corners to set yourself up with a flip-wedge, you can play it to the fat of the fairway and get friendly with the 150 marker.

Once you find your way onto the greens, the real fun begins. The greens at Cyprian are very modern, very big, and very fun. With many different tiers, shelves, and funnel-pin opportunities, the greens reminded me of those at Crumpin-Fox Club.

Driver isn’t always the best choice on the 12th hole at Cyprian Keyes.

The Haunted ‘Ghost Cabin’ at Cyprian Keyes GC

It’s no secret that I find uniqueness and character to be the keyes (see what I did there) to a memorable golf course. So when I heard about the haunted ghost cabin on the golf course, you can imagine how excited I was to get out there and see it.

On the 9th hole of the championship course at Cyprian Keyes, you can see a small gathering of trees, and set within those trees is a stand-alone chimney. Before the golf course was built, a cabin accompanied that chimney. And legend has it, the cabin was a Speakeasy back in the 1920’s.

When the course was being constructed, the builders spoke of suspicious ghostly activity regularly coming from the cabin. And when the cabin was “destroyed” the chimney never budged. The staff was unsure how to interpret this omen and decided to leave the chimney, which can still be seen today.

A Spooky Scene: The remains of the ‘Ghost Cabin’ at Cyprian Keyes.

Unexpected Discovery: The Perfect Golf Hole

One other discovery I made on this trip was a candidate for “best golf hole in Massachusetts.” Bold statement, I know. But hear me out. The 13th hole at Cyprian Keyes GC checks a lot of boxes, including the ‘will you remember it’ box.

What makes it so memorable? It’s a risk/reward par-4 that gives you the option to take driver and give the green a go. It’s set beautifully with a stone walled tee box, a picturesque sanctuary area to carry, with the hole shaped as a dogleg left. There is thoughtful bunkering, massive trees lining the back of the landing area, a stretch of fairway just four yards wide, a 3-tiered green, and of course, a bit of spooky history. The small collection of trees to the right of the fairway is the ‘ghost cabin’ area referenced above.

The real badge of honor is that this hole has the ability to dish out scores ranging from 2-8, which is pretty impressive for a par-4. I can only imagine how big the range of scores would be if it weren’t for the local rule, which has the drop zone located on the fairway side of the forced carry.

A throwback photo of the 13th hole at Cyprian Keyes during fall foliage. (Stephen Hanjack, 2018)

In Conclusion

I was excited to find yet another way to spend a day on the golf course here in Massachusetts. My newfound appreciation for par-3 golf courses has me hopeful to find more across the state. I found the championship course to be much more playable than I remembered – you just need to to pick your spots and play with patience. And most importantly, for parents with the golf bug, I think we found your perscription.



8 a.m. – Drop-off at daycare

8:20 a.m. – Arrival at Cyprian Keyes GC

8:40 a.m. – Tee Time on Par 3 Course

9:45 a.m. – Snack & chat with staff

10:30 a.m. – Tee Time on Championship Course

2:30 p.m. – Round complete

3 p.m. – Home for a shower and change of clothes

4:30 p.m. – Pickup at daycare



Keys to a Successful Parent’s Day – Start getting ready the night before. Check your bag the night before for balls, gloves, etc. Have your golf clothes laid out and ready to go for the morning. And if you really want to save some time, throw your golf shoes on before you leave the house.

Fall Foliage – Cyprian is definitely on my “All Fall-Foliage Team”, something to keep an eye on this October.

Aerification Done – Good news if you’re looking to play Cyprian this year, aerification is done. The greens were just about healed when I visited (Aug. 20). By the time you read this, they should be back to normal for the remainder of the season.

Public Home of Top Amateurs – This year, a lot of players from Cyprian Keyes have found their way to the top of Mass Golf leaderboards. Most recently, at the Massachusetts Amateur Public Links Championship, 7 players from Cyprian made the cut. Among those was Daniel Falcucci who finished T4 to earn his sixth top-5 finish at the APL in his career.

Golf Joke of the Day – Came from one of the guys I got paired with, Craig, who recently won the Net Division of the Club Championship. Gave a little ribbing to Mike, who had yet to replace the flagstick on any of the holes played.

Craig: “Hey Mike, how much does the flagstick weigh”

Mike: (with a perplexed look on his face) “I have no idea”

Craig: “Why don’t you try picking one up”

Golf, Golf and More Golf – If golf is your thing, Cyprian Keyes is your place. They have an 18-hole Championship Course, 9-hole par-3 course, full driving range, short game area, practice putting green, fitting center, well stocked pro-shop, restaurant, banquet hall, and a friendly staff.

Thanks again to Mike, Craig and Mike for showing me around Cyprian Keyes GC.



Have an idea? Want me to visit your course? Send your ideas for a special day of golf and I might show up –

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A Special Thank You to David Frem for helping making this journey possible.