Golf Staycation - Trip 1 - MASSGOLF

Massachusetts Golf Staycation

What’s the best part about a golf trip – The golf itself? Experiencing a course you never knew existed? Competition amongst friends? Experiences on the road? The food at the end of the day?

Whatever your answer might be, we can assure you that everything you enjoy about a golf trip can be experienced right here in the Bay State. With the uncertainty around travel this summer, we are encouraging our Mass Golfers to consider a Massachusetts Golf Staycation this year.

What is a Massachusetts Golf Staycation you ask? Quite honestly, it can be whatever you want it to be…as long as you are looking to play some golf. It can be 3 rounds of golf in one day, across 400 miles. It can be 7 different courses in 7 days. It can be playing the hidden 9-hole gems around the Cape all in one day. It can be playing a municipal course from sun-up to sundown for just $25. The possibilities are endless.


Trip #1 – A Route 2 Adventure (By: Stephen Hanjack)

Waubeeka Golf Links, Williamstown

Crumpin-Fox Club, Bernardston

Red Tail Golf Club, Devens

Photo: Crumpin-Fox Club’s 7th Green

When people talk about their favorite golf vacations, they often talk about wild locations, beautiful views, championship-style courses, and memorable moments. When I initially pitched this idea of: dreaming up, experiencing and writing about different Massachusetts Golf Staycations, I knew that I needed something crazy, something memorable, and something that has never been done before.

With that, I present to you my first suggestion (hopefully of many) of how to turn your canceled summer golf trip into a Massachusetts Golf Staycation. I will warn you, what you are about to read is a little crazy, very ambitious, and probably not for everybody.

As you’ve probably put the pieces together by now, my idea was to travel to the furthest corner of the state and work my way back east, playing golf all along the way. In doing this, I believe (please feel free to correct me if I’m wrong) I am the first person EVER to play the following three courses in the same day: Waubeeka Golf Links, Crumpin-Fox Club, and Red Tail Golf Club. Let me be the first to tell you, this idea looks way easier on paper than in reality! While it wasn’t easy and at times even grueling, as I look back now, I can say with confidence…this was the most memorable day of golf of my life.

If you’re still reading this, you’re probably an avid golfer yourself, so hitting the road at 5 a.m. is something you’ve surely experienced in your golf travels. To make it out to Williamstown for my 8 a.m. tee time at Waubeeka Golf Links, that’s just what I did. On the 2 ½ hour drive, I did what I believe every golfer does on the way to the course, I dreamt about shooting the best round(s) of my life. And just when I was starting visualizing that final birdie, I looked up and saw one of the most beautiful settings in my life. While I’ve been up the Berkshires a few times in my life, I never admired the stunning mountains, rivers and charm the way I did on this day. And that’s when it hit me…while I really hope I play some good golf today, who cares if I don’t? No one. So, when those visions of birdies turn in to generous gimme’s for double, I vowed to just grab my camera, walk to the next tee box, and take in all the beauty that Massachusetts golf has to offer.

First up was Waubeeka Golf Links. The second I walked into the pro shop, I knew I wasn’t east of 495 anymore. The friendliness and charm of Waubeeka was evident with my first interaction of the day. Ricco helped get me situated for my first round of golf and was generally excited about the idea of this trip starting with Waubeeka. Before helping me hurry out onto the course, Ricco quickly showed me his award-winning invention – The Media Stick – which can be used for golf course filming and the like. A fine invention indeed, but he could sense I was a man on a mission. With my calculations, I had exactly 2 hours and 40 minutes to experience whatever Waubeeka had to offer before needing to hit the road to get to Bernardston for my next tee time, scheduled for noon.

As Ricco sent me on my way, he had one last bit of friendly advice…make sure to keep that first tee shot left of the big tree. Great. As a “power-fader” (aka slicer) of the golf ball, you can guess exactly where that first tee shot went – right of that big tree…and smack dab in the middle of a pond. Not the start I was hoping for, but whatever, I was on my way. As I finished the first hole, I took a moment to look around and what I saw was beauty in every direction. Well-manicured greens, handcrafted wooden statues, stunning mountains and a perfectly empty golf course ahead of me. Playing the first 4 holes in approximately 20 minutes, you could say I was moving. And just as I sent my first birdie of the day to the bottom of the cup, one of the nicest people I ever met came pulling up.

Owner, Mike Deep joined me for the last 14 holes of the day, and it was a good thing he did. While I didn’t play terribly on this morning, I certainly wasn’t sharp, and I knew early-on a good score wasn’t in the cards. But none of that mattered, I was too busy watching the owner of this golf course passionately care-for and explain the features of his course. His happiness and friendliness is something you don’t often find these days, and quite honestly something I wish I had a little more of.

There wasn’t a single piece of trash (not that there was much) that we passed, where Mike didn’t stop his cart to clean up. He had a smile on his face from the second I met him until the second I left. Every person we passed – be it other golfers, the superintendent, other grounds crew members – Mike stopped to say hello and introduce me. As we played his collection of stunning golf holes he took the time to explain a little bit about them all. For example, the 13th hole (under the direction of former owner James Goff) was created to mirror the 10th hole at Yale Golf Course. Goff graduated from Yale and was captain of the golf team during his time there. Having been lucky enough to play Yale, I could immediately see it – the stairs that sat between two greenside bunkers helping golfers make their way to the severely elevated green. The other hole that is one I won’t soon forget was the 17th which has a replica green of the Road Hole at St. Andrews.

My last take on this course will surely be controversial – but here it goes – it honestly reminded me of playing golf in Hawaii. One thing people don’t realize when they book a tee time in exotic places like Hawaii is that every hole isn’t set along the coast. Much of the course is set inland, with hotels and beaches getting the majority of ocean views. With that, you are often playing elevated holes with large sloping land and huge mountain/volcano views at every turn. At Waubeeka, as I stood on each green and looked around, there were enormous mountains in every direction. And if only for a moment, it felt exactly like Hawaii.

We finished the round at 10:30 a.m., which gave me exactly 10 minutes to get in the car and on my way to Crumpin-Fox. Mike could sense that I was in a rush, so he knew I wouldn’t be stopping for any food along the way. The restaurant was closed, but Mike (again the owner of this course) fired up the grill and whipped me together one of the biggest burgers I’ve ever eaten. And since he knew my background from our time on the course, he knew that I actually played baseball against Williams College at their field just up the street. Knowing that the field was on my route to Bernardston, Mike wouldn’t have it any other way than for me to enjoy an old baseball memory by stopping at that field. You must be thinking, “oh that’s nice he pointed you in the right direction”…wrong. Mike (again the owner of this golf course) hopped in his car and led me directly to that field to make sure I wouldn’t miss it. And as we parted ways, Mike left me the same way he met me, with a friendly wave and a huge smile on his face.

Once I was back on the road, I could see from my GPS – I was in trouble. My next tee time was set for noon, and my estimated arrival time was 12:09. This leads me to HELPFUL TIP #1 of a journey like this – Be Ready For A Change of Plans. From the start, I knew completing this trip was going to be a stretch. So when I fell 10 minutes behind schedule, I conceded that I might not be able to complete all 54 holes on the docket. In being able to grab the first available tee time at Waubeeka, I was able to play 18 holes in 2 ½ hours…something I knew would be impossible mid-day. Before calling Crumpin-Fox to bump me back 20 minutes, I made a hairpin turn on Route 2 with one of the most stunning views these eyes have ever seen. A view that was too good to pass up. So I pulled over, jumped out of my car and quickly snapped a few photos of the amazing mountain scenery.


On a day where temperatures would nearly reach 100*, I was only 18 holes into a 54 hole day, and I was already feeling gassed. Not a great recipe when pulling up to a location that was conceived in 1969 as the “field of dreams” of David Berelson, who engaged the services of Roger Rulewich of Robert Trent Jones, Inc to locate a site that would accommodate a Pine Valley type golf course.

I was again greeted by a number of happy faces (all with masks, mind you) that made me feel like I was doing them a service by visiting their course. I can’t stress enough how a happy encounter and a friendly attitude can make a golfer’s experience a memorable one, regardless of score. The general friendless of every staff member I encountered on this crazy day gave me inspiration to become a more approachable person.

I started my round the same way I started at Waubeeka, reaching for another ball after blasting my opening tee shot into a place that would surely be listed as “unknown area” if my round was being tracked on the PGA TOUR App. As I got to the first green, I quickly remembered what type of course I was at. This is a Championship Golf Course in and its greens rival those of any stop on the PGA TOUR. Golfers always say, I want to see what it’s like to play on those hard, fast greens that are in perfect condition, and see how I’d do. Well at Crumpin-Fox, you can certainly get a taste of what that is like.

While the course just hits you with stunning hole after stunning hole, cut perfectly amongst the trees, it dawned on me…this is a special place. While it certainly has stern challenges along the way, I found it to be a very fair test of golf and quite enjoyable. And for my money, I don’t know if you can find a more photogenic trio of holes than 7-9. As I continued to snap picture after picture and get caught up in the undulations and overall perfection of the greens, I lost track of the time. I also began to lose track of my hydration. Luckily the beverage cart arrived (somewhat surprisingly) as soon as that thought hit me. I couldn’t scream the word Gatorade fast enough when she pulled up and proceeded to consume Gatorade’s number 2 and 3 on the day.

This leads me to HELPFUL TIP #2 – pack a giant cooler with bunch of water and sports drinks for the trip. Throw a couple in your bag at each course and be sure to purchase a few from the course as well. Let’s make sure we’re throwing them some business, too. You’re also going to need some while you’re on the road, and with an itinerary like this, there is no time for stopping at gas stations.

As I made the turn at Crump, the grind of the trip was taking its toll. You’re probably thinking, “oh quit your whining, you’re on a golf course…and not just any golf course, you’re at Crumpin-Fox! No one feels bad for you.” Thinking about what those responses might be was exactly what I needed. And to make it through the rest of this trip, I needed to set a goal. But my hands were feeling swollen, my legs were feeling heavy and I lacked the hop in the step that would have been needed to set a score-related goal. Briefly looking ahead to my upcoming 3rd round of the day at Red Tail, I mentally circled the 17th hole. For whatever reason, in all of my golf travels, the 17th hole at Red Tail is my favorite hole in Massachusetts. At that moment, at the snap of a finger, the only thing that mattered was getting to that 17th hole.

With my tee time at Red Tail lurking at 5 p.m., I still had an hour and a half of golf that I could squeeze in at Crumpin-Fox. With as popular of a course as it is, there would be no way for me to snake my way around the entire back nine that quickly – especially with some of the swings I was making. On the back nine, I made the most important adjustment of the day, I started thinking about THIS golf shot. Forget about score, forget about the last swing, forget about the next swing, just hit THIS shot. As soon as I did that, I found it. Slowly my game started coming back. All of a sudden the ball was flying off the driver again which led to a few more wedges into the greens. After getting lost in the beauty and perfection of the greens on the front nine, I started to get the feel for them on the back nine. Hitting the ball to the proper section of the greens certainly helped, but 3-putt doubles had been exchanged for tap-in pars.

As I made some final calculations out on the course, I estimated that I’d be able to make it to through 15 holes at Crump before needing to depart for Red Tail. And with that, my dream of completing all 54 holes evaporated. But that was okay, because if I could get to that 17th hole at Red Tail, it would be an even 50 – and still a heck of a day. After playing holes 11-13 quite nicely, it hit me, I hadn’t made a birdie since the 4th hole at Waubeeka. Part of my intention in writing this piece would be to lay. out my map, give the number of holes played, number of birdies made, number of golf balls lost, etc. as a checklist for anyone interested in replicating this trip. Essentially giving them something to shoot for. Guess what doesn’t make for much of a goal, 1 stinkin’ birdie. The next two holes were the par-5 14th and the short par-3 15th. On 14 I hit a beauty off the tee, squeezing it between the bunker left and penalty area right. I bailed out right (with water left) with my 3-wood into the green, but bounced back with a nice chip to the upper shelf where the hole was located. Here it was, my chance to add birdie number 2 to my day. I put a good stroke on it, but just carried a little too much pace and power-lipped it out. Then on the 15th I finally hit a mid-iron nicely. No birdie, but that swing with the 7-iron was exactly what I needed to bring a hint of confidence back to my game.

Looking back at my round at Crumpin-Fox, I’ll remember 3 things. The first is the setting and layout of the course. I don’t know if it was their intention, but you could honestly put any one of their holes as the closing hole at a course, and you would have done well. Every hole is different, every hole has character and every hole is memorable. The second thing I’ll remember is those greens. When the U.S. Open comes around in September and we all start looking for courses that will give us that U.S. Open feel around the greens, Crumpin-Fox will be my first call for a tee time. And third, I’ll remember it as the place where I found my game again. And while I can’t explain why, there was just something about that place that reminded me how golf is meant to be played.

So 33 holes into my day, it was back to the car (which read 106*) and on the road again. But before hitting the road, it was time for a few changes to my wardrobe, which brings me to HELPFUL TIPS #3, 4 and 5. After playing 33 holes in the heat, it was time for a new polo, new socks and a re-application of deodorant. If you plan on making this trip, an extra couple of polos, an extra few pairs of socks and a stick of deodorant is a must. If not for you, for the people you encounter.

As I pulled up to Red Tail, I had one thing on my mind – the 17th hole. Upon checking-in I figured it was worth asking if there was a way to start on the back. But what kind of story would that be? Off the front it was. As I pulled up to the 1st tee, I ran into what I thought was going to be the end of my journey…league play. I’ve played in enough Thursday Night Leagues to know what it means to follow league play.

But then, as if he was sent from a higher power, a nice gentleman came walking back to me from the tee box. “Are you with anyone, or are you playing as a single?” Before I knew it, I was teeing it up with Mike and Scotchie, and saying a silent thanks to whoever their opponents on this Monday night were supposed to be. And as I teed it up at 5:08 p.m., my dreams of reaching the 17th hole were fully intact.

As I’ll write about later in this post, another thing that I love about Red Tail is the setting. Situated on the land that was once part of Fort Devens, there are bits of history all around the course. From a hole that used to be a tank crossing, to a fairway that is shaped by housing foundations beneath the turf, to a military lookout tower next to the 18th tee box, there is enough history around this course to keep you interested no matter what your score.

I don’t know if it was the excitement, the friendliness of my playing partners, or what…but I came out playing some golf. I found every fairway on the front and only missed a few greens. Before I knew it, I put together my best 9 of the day, just a couple over par. But while I was telling stories and getting to know Mike and Scotchie, I had lost track of the time. With their league play finishing up after 9, they offered to join me as I set out for the back nine. Now approaching 7 p.m., it was crunch time if I was ever going to make it to 17. After a boring par on the par 5 10th hole and a rushed 3-putt bogey on the 11th, my partners could sense that I needed to get a move on. They graciously suggested I rush ahead as they were not as invested in getting to the 17th hole as I was.

It’s funny how you can find symmetry in stories. On this day I found it in the way I departed. Similar to how I was greeted by Mike at Waubeeka, with a friendly smile just as I finished knocking in a birdie…I departed with a friendly wave and smile. And wouldn’t you know it, the first hole I played on my own was my best one of the day. Two perfect shots leaving me just 1 foot for birdie. A simple little kick-in and I was off to the races, literally. I started running to the cart, whipping ahead to the next tee box, and hustling out there to tee it up. After another pair of perfect tee shots, good approaches, and boring two-putts, I found myself even par through 5 and in a dilemma. Do I slow it down and take each shot more serious to see if I could get this back-nine under par? Or do I keep the pedal to the metal to make sure there would be enough daylight to reach 17?

Pedal to the metal it was. The sun was dropping quickly, but with no one ahead of me and with the way I was hitting it, reaching the 17th now almost felt like a certainty. After a silly bogey on 15, I again hit a perfect tee shot on 16. But then, my greatest fear hit me, laughter. I could hear it from just over the crest of the hill as I finished hitting that blind tee shot. With maybe 10 minutes to spare before absolute darkness, there is no way this story can end with a group halting me on the final tee box!

Rattled, I took a deep breath and hit a nice little wedge inside 10 feet. Looking ahead to the 17th tee box, I could see the group was still on the tee, and in no hurry. I still can’t find the words to explain the wave of emotions that were hitting me at that moment. Are you kidding me? My 4:30 a.m. alarm, the 4+ hours in the car, the 8+ hours on the course, all of it coming to an end just 20 paces away from my goal.

Somehow, I managed to hold my composure enough to knock in the testy little 8-footer for birdie, which got me back to even par on the back. It was definitely getting dark, but as I jogged back to my cart and floored it around the corner to the 17th tee box, I knew. It was happening.

7:55 p.m. and I made it! All of the stress I put on myself (for no reason), all of the rushing around, all of pep-talks, everything…it worked. There was one thing I wanted to accomplish on this day, and I did it. I reached the 17th hole. Being a golf photo junkie, I grabbed my camera and headed up to the tee box.

The group ahead of me that gave me my final little scare of the day was just getting to the green as I set-up to snap a few photos. Although it was starting to get quite dark and difficult to see, I figured I would wait the extra 5 minutes (which felt like 45 minutes) for the group to clear. I wanted to have a moment. Just me and the 17thhole. Not a soul in sight. At 8:03 p.m. the group was gone and I quickly snapped a dozen photos of my favorite hole.

Photo: The 17th hole at Red Tail, with darkness setting in

I guess the only left to do was finish on a strong note. Although the hole reads 390 yards on the card, it is one of those bite-off-as-much-as-you-can-chew dogleg par 4’s. With an expansive sandy area protecting the right side, I told myself “Today is the day.” I’m going to knock it on this green. I had one last wave of adrenaline in me, and now feeling invincible, I saved my best drive of the day for last. It was a beauty starting just left of the green and gently fading right. But then, poof. The 280 yard carry proved to be just a yard out of my reach, and into the sandy area I went.

No problem, let’s knock this long bunker shot on the green and give ourselves a chance at one last birdie. I caught it good, but had a little too much bite on it and came zipping back off the front of the green. Staying in the moment, I hit a beautiful little chip shot to 3 feet. So here I was, with 3 feet left for par, on my favorite hole, to close out an amazing story and day. I took an extra second to give this putt the attention it deserved. I had my read. Left edge, firm. I settled in and as I sent the putter through, I felt it. That dreaded feeling when you know right away that you pulled it. I watched as it headed just outside the left edge…

But then, as if it was placed there by a higher power, the most beautiful little pebble that ever existed sat waiting. *Boop* Off the pebble my ball went, making a hard right and into the bottom of the cup. I don’t know how it happened, I don’t know how I never saw it there to begin with, but it happened. I made it through the 17th hole, and did it in the most spectacular fashion. After all of the driving, all of the golf, 50 holes were now in the books. What a way to end the day…I thought.

As I skipped to my cart and pulled up to the 18th hole, I felt that there was just enough light left to maybe squeeze in this last hole. Now even par through 8, and floating on cloud 9, I thought this was another sign from the golfing gods.

I teed it up on 18. As I pulled the driver back, I started to hear a buzz coming from behind me, but I stayed in the moment and ripped one final drive right down the middle of the fairway. As my ball fell gently out of the sky, that buzz came rushing past me. That buzz was a moped with a couple of riders. Very odd for a golf course I thought, but on I went. As I got to my ball in the fairway it started to dawn on me, I think I should stop. I think that moped was a sign to end this story here.

But I was sitting 219 out on a par 5 with a definite chance at breaking par on my final 9 holes of this marathon day. And as I approached my ball, another sign to stop…the group ahead of me was battling with this closing hole, and the hole was winning. It seemed like everyone in the group was taking a drop and looking deflated. Odd I thought, but no sense in stopping.

As they finished up and as I pulled hybrid, a 3rd sign to stop…a group appeared out of nowhere and had driven their balls just behind me in the fairway. And then a 4th sign to stop…a golfer appeared 100 yards behind me on this 18th fairway. He saw me, and decided to give it go anyways, hitting a ball right past me as I sat in that fairway. All of it, odd.

So with 4 signs to stop, I did what any golfer would do, stubbornly proceed in my quest to break par on this closing 9. I’ll fast forward past the sloppy swings moving me towards the 18th green. I now sat just paces away from this 18th hole with a shot at making par. And that’s when it happened. At that moment I decided the signs were enough. This day deserved to be remembered for 17, it wasn’t about this back nine score.

What did I do, you’re wondering? I walked up to the ball, picked it up and tossed it to the bottom of the pond sitting next to the 18th green. We will now never know what I shot on this crazy day…and you know what…that’s how I prefer it. This whole trip was meant to be a journey. And now I can assure you, it is one I’ll never forget!

In Conclusion

This specific trip might not be for you. Maybe it’s just one of these courses at a time. Maybe it’s some of the lesser known courses that tickle your fancy. But if you are at least starting to dream up some crazy idea for golf in Massachusetts, I’ll consider this a victory. I’ve played hundreds, maybe thousands of rounds of golf in my lifetime. And it was a random Monday in July, staying in my own state, where I played the most memorable day of golf in my life. I will never forget this experience and I hope you have the courage to dream big.


A Little Bit About The Courses

Waubeeka Golf Links – Book A Tee Time

As I wrote earlier, I had absolutely no idea what to expect when I set out on this journey. But I have to say, I was blown away by my experience at Waubeeka. A few of my takeaways from the course and apologies if any of this sounds repetitive:

  • The course sits between the mountains of Massachusetts, New York and Vermont, and the views rival that of any destination course. As I mentioned in the story…it reminded me of golf in Hawaii. As I stood on each green and looked around, there were enormous mountains in every direction. Even without the Pacific Ocean nearby, it felt exactly like Hawaii.
  • The condition of the course was spectacular. It was as green as could be, well maintained, and absent of any trash or debris.
  • The layout was a ton of fun. There are a bunch of unique holes, some look-alike holes (Yale’s 10th hole and St. Andrews Old Course 17th hole), and a number of other beauties as well. While there are plenty of challenges along the way, I also enjoy playing golf where holes run alongside each other. Having holes like this make it possible to recover from wayward tee shots, which is ideal for average players like me.
  • This place could easily host top level competitive events. They keep the greens at a nice quick speed, but if they ever had to really speed them, they could. And with the expansive green complexes and undulations, they would provide a stern test for the best golfers around.
  • Statues – There are a number of hand-carved wooden statues around the golf course, all of which add to the character of the course.


Crumpin-Fox Club – Book A Tee Time

Rather than repeating much of the same listed above. I think the best way I can describe Crumpin-Fox is from this excerpt from the story above: Looking back at my round at Crumpin-Fox, I’ll remember 3 things. The first is the setting and layout of the course. I don’t know if it was their intention, but you could honestly put any one of their holes as the closing hole at a course, and you would have done well. Every hole is different, every hole has character and every hole is memorable. The second thing I’ll remember is those greens. When the U.S. Open comes around in September and we all start looking for courses that will give us that U.S. Open feel around the greens, Crumpin-Fox will be my first call for a tee time. And third, I’ll remember it as the place where I found my game again. And while I can’t explain why, there was just something about that place that reminded me how golf is meant to be played.

If you ever make it out to Crumpin-Fox, bring your camera! Every hole is photo-worthy, but the stretch of holes 7-9 are by far the best of the best. Dramatic, beautifully tree-lined, water adjacent, changes in elevation…these holes have it all.


Red Tail Golf Club – Book A Tee Time

Anyone that knows me, knows that I’m a sucker for a good story behind a golf course or a golf hole. The course itself is situated on the land that was once part of Fort Devens. With that comes a number of interesting stories about the holes.

  • Hole 2 – Named “Tank Crossing” because the area between the first and second landing areas was used as a tank crossing many years ago.
  • Hole 10 – Named “Foundations” because the rolling terrain found on this fairway is largely the result of housing foundations that once occupied this area.
  • Hole 11 – Named “Gravel Pit” was the old gravel pit on base.
  • Hole 17 – Named “Bunker” not for its large expanse of sand, but for the ammunition storage bunkers that dotted this area. Some of them can still be seen today, right of this green.


By The Numbers:

Miles Traveled – 395

Time In Vehicle – 5 Hours and 30 Minutes

College Baseball Fields Visited: 1

Time On Golf Course – 8 hours and 57 Minutes

Holes Completed – 50

Birdies Made – 3

Pars Made – 22

Score on 17 at Red Tail – 4

Golf Balls Lost – 10

Gatorade Consumed – 112 ounces

Soda Consumed – 40 ounces

Best Sign Seen – Bear Crossing

Best Town Name – Florida (Yes, there is a Florida, Massachusetts)


Have an idea?

Send me an idea for one memorable day of golf and I might just give the ol’ college try –

Photo: If you’ve ever seen this guy at an event, that’s me.