The Berkshires’ Best 18 Holes

Richard Lord travels the Berkshire to build his dream golf course.

Stockbridge Golf
The Housatonic River snakes its way through the Stockbridge Golf Club’s challenging course.

By Richard Lord
Photos by Ben Garver

When asked by the editor of UpCountry to produce a list of Berkshire County’s best holes to celebrate the dawn of a new golf season, I was reminded of an equally daunting assignment I received in the late 1990s.

The newspaper I was working for in North Carolina had a Sunday feature that was the written version of ESPN’s “First Take” and I was given the task of arguing — in Tar Heel country, no less — that Michael Jordan wasn’t the greatest basketball player ever. While I think I made a good case that others were at least his equals, I don’t think I convinced any UNC alums.

The same will likely to be the case with Berkshire County’s avid golfers. Any ranking of holes is highly subjective. Are we talking the toughest 18 holes? The longest? The prettiest? The most strategic? I tried to take all of those things into consideration and attempted to produce a course that would be fun for all when played from the tees that best suit your game.

The distances listed below are from the back tees, so most of the holes play considerably shorter for the majority of us who don’t belong on the tips. I have placed a limit of holes from any one course at three — Taconic Golf Club, which ranks as one of New England’s most honored courses, leads the list but as many as half of the holes at the Wayne Stiles-designed classic deserved consideration.

The odds that any of you will agree with all 18 choices is about the same as picking a perfect NCAA Tournament bracket.

Let’s tee it up.

1. Taconic Golf Club, Hole 12

Par 4, 377 yards
This is the shortest par 4 on the list but it’s no pushover. The tee shot is uphill across a deep ravine that runs down the left side. The best approach angle is from that side but out of bounds looms nearby. The green features a false front that will send shots that come up short back down the fairway.

2. Berkshire Hills Country Club, Hole 2


Par 5, 560 yards
The downhill tee shot is a risk-reward shot for the long hitters. Those who find the fairway can reach the bottom of the hill, making it possible to reach the green in two with their uphill second shot. However, a hooked tee shot could end up in the trees or out of bounds. Trees also protect the right side of the fairway.

3. Wahconah Country Club, Hole 2

Par 3, 220 yards
Members and visitors alike get an early test with their long irons, hybrids and fairway metals on a long par 3 that is protected by bunkers on both sides.

4. Wyantenuck Country Club, Hole 4

Par 4, 440 yards
The longer hitters can shorten this hole by cutting the corner of this dogleg right while those who hit it left will likely go through the fairway and into the trees. The difficult second shot is uphill, playing perhaps two clubs longer than the yardage, to a challenging two-tiered green protected by a bunker on the right.

5. Berkshire Hills Country Club, Hole 6

Par 4, 430 yards
A classic A.W. Tillinghast cape hole with water guarding the right side of the fairway. The longer hitters can attempt to shorten the hole by cutting across the water but an overly aggressive line can quickly lead to a big number.

6. Stockbridge Golf Club, Hole 5

Par 3, 121 yards
Every 18-hole course needs a challenging short par 3 and this one fits the bill. With the Housatonic River in play short and to the right of a small green that is protected by bunkers, plenty of things can go wrong despite the hole’s length.

7. Greenock Country Club, Hole 3

Par 4, 408 yards
This dogleg right is a difficult driving hole that requires a fade with most of the longer hitters going with long irons or hybrids. A hooked tee shot will find tree trouble as will any straight drive that goes through the fairway.

8. GEAA, Hole 6

Par 5, 570 yards
The downhill tee shot will get plenty of roll with the biggest concern, at least for the longest hitters, being a pond to the right of the fairway. It’s all uphill after that to a tricky green that is sloped right-to-left and back-to-front.

9. Wahconah Country Club, Hole 9

Par 4, 413 yards
This par 4 is both an excellent front-nine finishing hole and one with historical significance. It plays longer than its length with the second shot steeply uphill to a green guarded by bunkers on both sides. There is a plaque behind the green signifying it as the last hole the legendary Bobby Jones played in competition.

10. Cranwell Spa & Golf Resort, Hole 9


Par 4, 411 yards
One of the tightest driving holes in the county with trees left and out of bounds right. If that isn’t enough, the second shot is uphill to a putting surface that can’t be seen from the fairway.

11. Country Club of Pittsfield, Hole 8

Par 5, 562 yards
A right-to-left tee shot is preferred on this strong par 5. That accomplished, a layup to the left will avoid a hazard on the right while also providing the best angle for the third shot. The green is protected by two deep bunkers on the right and is extremely fast from above the hole.

12. Wyantenuck Country Club, Hole 17

Par 4, 401 yards
An accurate drive is needed with a miss, especially one to the right, likely resulting in a lay-up shot to the bottom of the hill that rises to the green. The green is set in a bowl, which can create some interesting chip shots.

13. Country Club of Pittsfield, Hole 13

Par 3, 162 yards
The club’s signature hole is a classic downhill par 3 that features a view of Mount Greylock in the distance. With a 40-foot drop from tee to green, picking the right club is a challenge.

14. Waubeeka Golf Links, Hole 11

Par 4, 402 yards
A visual beauty, but a difficult par. Avoiding the left rough and finding the left-to-right sloping fairway is crucial. The course’s deepest bunker fronts the right side of the green while the putting surface has plenty of humps and bumps.

15. Taconic Golf Club, Hole 16

Par 4, 460 yards
Possibly the Berkshires’ toughest par 4, this uphill monster requires two strong shots just to reach the green. Once you get to the putting surface it doesn’t get easier — it is pitched severely from back-to-front, making it crucial to stay below the hole.

16. Taconic Golf Club, Hole 17

Par 3, 246 yards
After golfers at Taconic breathe a sigh of relief after surviving one test, they face another. Not only is this a long hole that can require a 3-wood for low handicap players, it features Taconic’s most feared green, one that makes it better to be short of the green than 10 feet above the hole.

17. Waubeeka Golf Links, Hole 17

Par 5, 501 yards
After playing three long par 5s, it’s time for a reachable par 5. The tee shot, with Mount Greylock providing a beautiful backdrop, is blind but for long hitters who find the fairway — which is said to be a replica of the Road Hole at St. Andrews with its many humps and bumps — the shallow green is usually within reach.

18. Stockbridge Golf Club, Hole 18

Par 4, 444 yards
A slight dogleg right, this solid finishing hole more often than not is played into the wind. The Housatonic River and trees guard the right side and there is out of bounds both behind the green and to the right.

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