Where the Game Takes Us: GreatHorse, Hampden, MA

There's a certain anticipation that always seems to build for me when I drive west on the Mass Pike. Those mile-long hills are massive in my SUV going 70 mph. But something about the imagery of Henry Knox doing this with his 55 cannons stolen from Fort Ticonderoga in the dead of winter always gets to me. But not today. Today, my focus was the two years of texts and planning calls with Bill and Jared that were finally coming together. The calendar read October 1st. The leaves were at their peak. GreatHorse was waiting.

It was a perfect fall day in Western Mass when I made the turn up the long and winding road that leads to GreatHorse Country Club. The ridges on the horizon seemed to be painted in gold and crimson, and the perfect green grass above and below outlined what immediately seemed like a golfer's paradise. I had heard so many stories about this completely re-designed Brian Silva staple, but I was finally going to see it for myself.

GreatHorse is no ordinary club. The Antonacci family, known for their racing legacy, transformed the old Hampden Country Club into a $50 million private retreat. Brian Silva's vision is everywhere—everything is new, from the irrigation and bunkers to the fairways and greens. Only the original routing remains from 1973, but the soul of the place is fresh and bold.

At GreatHorse, the clubhouse sits atop the world—part mansion, part mountain lodge—with a view that makes you pause before you ever grab your clubs. It's opulent, welcoming, and feels like the gateway to a special day. We explored its halls, soaking up the anticipation. It's all polished wood and panoramic windows, the kind of place that feels both grand and welcoming. The outdoor open-air restaurant overlooks the fairways winding away below, and it seems like something you'd find in sunny California where it rarely rains. I can imagine spending many happy hours here after a hard-fought round. But first, I had to earn my celebratory drinks.

We met our hosts in the pro shop, and they gave us the lay of the land. We spent a short while warming up on the range past the upper parking lot, and then made our way back through the clubhouse to the first tee. Standing there, the entire valley spread out below, I felt the rush that only comes before something special. The par 4 first played 406 yards today from the tips, tumbling downhill. I watched my drive run and run—294 yards, leaving just a wedge in to a lower green. An opening birdie, and for a moment I floated above it all. Reality, of course, was waiting on the second tee.

A 558-yard par 5 from the tips, with a 230-yard carry over water to rough that looked hungrier than I was. After a hopeful swing, I still had 340 into a distant green. My bogey came far too easily, and I was back to even par.

Then came the third—where my playing partner Max's constant insistence that we play new courses from the tips started to rear its ugly head. It's a par 3 that plays 288 yards, a number that feels like a typo until you put pride aside and reach for the big dog. I pulled it left, but it bounced off the path to pin high. An awkward pitch led to a bogey again, and the round was only just beginning.

GreatHorse doesn't let up. The next stretch—4, 5, 6, 7—all played over 400, each with its own personality: sharp doglegs, greens perched atop ridges, fairways that seemed to ripple with color under the autumn sun. The 8th, a par 5 with a 248-yard carry over a sea of waste, ended with my first double. But by then, I was deep in golf-course appreciation mode, my score fading behind the scenery.

The ninth—a 178-yard par 3—felt almost gentle. I hit it to 8 feet. Max flubbed his tee shot chunky, and his ball landed 40 yards short of the green by the greenside bunker. He had been struggling with his wedges all week, so I thought for sure I would claim one victorious hole on this outward nine. I stood behind the green on a raised slope, and listened to him curse his wedge game while he addressed the ball. Predictably, he clipped it clean, the ball launched high over the bunker, landed just past the pin, and spun back. Incredulous, I realized he had holed out for birdie. My 8-footer suddenly had all the pressure in the world, which meant I lipped out. Golf's sense of humor was alive and well.

The back nine opens across the road, another downhill tee shot, the fairway sloping away toward the horizon. I found an awkward lie in the short grass, which meant I left myself a long snake of a putt to a front pin. But my missed 8-footer had imbued me with a new determination that I deserved something great. So I drained a 30-footer, and added another circle to my card. This game never stops surprising me.

Holes 11 through 13 test your nerve with forced carries and bunkers that seem to multiply as you approach. Fourteen stretches on and on, then turns for home. Fifteen—a mere 127 yards to a massive green—felt like a gift, a moment to catch my breath.

Sixteen and seventeen tighten up, tree-lined and strategic, with bunkers lurking just out of sight. Seventeen, especially, felt like launching a tee shot down a corridor of evergreens, the green hidden around a dogleg, daring you to trust your line.

And then, finally, the eighteenth. Standing on the tee, you can see the Berkshires in the distance, the clubhouse perched above it all, waiting. One last drive, across the road, up the sloped fairway, and back to where the day began.

There's a certain magic to golf in New England this time of year, and GreatHorse makes the most of it. Every shot feels like you're launching a ball into a postcard.

This was a day that had been a long time coming. GreatHorse tested every part of my game, but more than that, it reminded me why we chase these experiences. For the challenge. For the camaraderie. For the moments you can't script, and the views you can't forget.

We'll be back with the Bucket List Crew in '26.

Will you join us Interested in a private or hosted event for your organization or next buddy's trip? next?

Chris Leary
Founder & Tour Director
Bucket List Series