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In 1844, 27-year-old Henry David Thoreau journeyed west from his home near Boston, then straight uphill, to the summit of his state's highest peak, Mount Greylock, near the town of Adams, sleeping alone in a cold observatory shack.
He came down a changed young man. The epiphanies from his journey seeking solitude in the forests and the mountains of the Berkshires helped inspire one America's greatest philosophical and literary careers.
Desires to meander and be enveloped by nature drive golfers out of their homes and into the landscape, too. Although they may not be on many top-10 or even top-20 lists of America's most visited golf destinations, in the summer, the Berkshires are a wonderful place to tote one's clubs and one's curiosity. Among quiet hills and pleasant towns, there are plenty of opportunities to walk, swing, contemplate and repeat.
5 Berkshires golf courses to consider
When people speak of the Berkshires, they are generally referring to roughly the western third of Massachusetts, west of the Connecticut River, between the borders the state shares with Connecticut to the south, New York to the west and Vermont to the north.
This vast area is home to several hamlets but only a handful of sizable towns like Great Barrington, Lenox, Pittsfield and Williamstown. Despite its relatively low year-round population, it is a long-time haven of artists and writers and therefore a hub of cultural activity, especially in the summer in places like Tanglewood, the satellite home of the Boston Symphony Orchestra. Museums devoted to authors Herman Melville (Pittsfield) and Edith Wharton (Lenox), activist Susan B. Anthony (Adams) and artist Norman Rockwell (Stockbridge) draw their share of visitors as well.
With all due respect, one can only look at paintings and old papers for so long. The great outdoors call, and there is plenty of golf to play across the Berkshires.
Taconic Golf Club
Were it not for the spectacular Yale Golf Course, This Wayne Stiles and John Van Kleek classic would lay a strong claim to the title of "best college golf course in America." Open since 1927 and, like Yale, touched up by latter-day architects Gil Hanse & Jim Wagner, it sits on the campus of Williams College, one of America's elite liberal arts institutions.
Taconic is a quintessential New England parkland golf course - a compact routing with relatively small and well-bunkered greens that pitch from back to front. The outward nine is on the sportier side at less than 3,200 yards, par 35, from the back tees, but the back nine brings three par 4s of more than 440 yards and a monster par-3 17th, tipping out at 246 yards. An early, literal sign of Taconic's staunchness: the admonition, "NO PREFERRED LIES - WE PLAY GOLF HERE!" posted outside the pro shop.
Most tee times at Taconic go to Williams' Division III team, alumni, staff and students, but guests can arrange to play on select days and at certain times. It is well worth the effort to snag a spot at an elite New England golf course.
Green fee: $180.
Crumpin-Fox Club
Henry David Thoreau would have appreciated Crumpin-Fox's deep-woods seclusion. Picture a stereotypical summer camp and route a golf course through it: that's the feel of Crumpin-Fox, a Robert Trent Jones, Jr. design that opened in 1990 in the town of Bernardston, about as far north and east as you can go in Massachusetts and still be considered part of the Berkshires.
Crumpin-Fox has been considered a worthwhile day-trip spot for golfers from Hartford, Providence and Boston for decades, fitting the "country club for a day" mold since inception. It sits in the #4 spot on our latest Golfers' Choice list of Massachusetts golf courses #15 on our New England list. The long par-5 8th hole, which curls around a pond to a dangerously perched green, has been one of New England's most photographed modern golf holes for years.
Green fee: $150.
Wahconah Country Club
Most golfers would never think to associate Bobby Jones with a relatively little-known semi-private club in New England, but on August 15, 1948, the ailing Grand Slam champion and amateur golf legend played his last round of golf there, leaving behind a letter reading, "This was my last effort; sorry it was not a better one."
The somberness of its unusual place in golf history is at odds with Wahconah's ethos. It is as warm and welcoming as anywhere one would wish to play, with a vibrant and unpretentious membership and atmosphere. People love their golf here, and non-members have the ability to book tee times most afternoons. The front nine of the golf course was built by Wayne Stiles in 1930 and the back was built in the '60s from Stiles' plans by Geoffrey Cornish. There is a stylistic shift from one nine to the next, which is common across New England, where many golf courses have added second nines decades after their original foundings. Wahconah's two-nine feel is less jarring than most, but still a bit of quirk that fits right in with the area.
Green Fee: $120.
Waubeeka Golf Links
Waubeeka, laid out by local World War II pilot-turned-golf architect Col. Rowland Armacost and remodeled in recent years by Mark Mungeam, will always hold a special place in my heart. It was the first place I ever won a golf tournament, at the age of 10. Granted, I topped a field of two total golfers in my age group.
Waubeeka sits just south of Williamstown on hilly property with some lovely mountain views. Mungeam's work has brought greater creativity to the bunkering and some more interesting greens to the course, including an appealing Redan-like par 3 on the back nine.
Green fee: $80.
Wyndhurst Golf & Club
More nostalgia for me at Wyndhurst, which, when I had last played it some 20 years before a June 2026 return visit, was known as Cranwell. More than just a name has changed here; what was once a sleepy spa resort is now a high-end, all-inclusive wellness retreat under the Miraval brand within the greater Hyatt empire. The Gilded Age mansion built on property in the 1890s presides over what is now one of New England's most fun first holes: a semi-blind 330-yard par 4 that plunges downhill to a teensy green. This was formerly the 8th hole, but various renovations around the property have made it the opener.
The Stiles & Van Kleek routing that dates back to 1926 is largely intact, but Mark Mungeam has recently made some welcome tweaks to the course, including mellowing several greens that had become too steep for modern green speeds. Usually these sorts of changes result in bland golf, but Mungeam did a good job of keeping them properly terrifying for golfers who find themselves above the hole while adding more viable hole locations. Select bunker work has also added definition on certain holes. The course was originally laid out for the enjoyment of the Wyndhurst mansion's owners and friends, and it retains the quirky charm one would expect from a course of that genre. Thankfully, the course is available for daily-fee play, and not restricted to overnight resort guests.
Green fee: $135.
Other notable golf courses in the Berkshires
Berkshire Hills Country Club (Pittsfield) - This A.W. Tillinghast-designed course opened fully in 1928, but the club was established in 1925 with the backing of early General Electric executives and employees. Similar to Wahconah, Berkshire Hills has allowed non-member play in off-peak times in the past. The club also hosts multiple amateur tournaments each year.
Greenock Country Club (Lee) - Golf has been played on this property since 1895, but Donald Ross redesigned the nine-hole course in 1927. It remains a vibrant club that takes non-member play daily, with peak 18-hole green fees in the $75 range.
Country Club of Greenfield (Greenfield) - Another pre-1900 golf course, this one has both Alex Findlay and Ralph Barton in its design background, with small, tricky greens and a railroad line through the middle of the property. Greenfield hosts a best-ball match-play event every July that recently celebrated its 81st playing. Green fees sit around $65.
Country Club of Pittsfield (Pittsfield) - This private club blends the region's two main classic design influences. Donald Ross laid out the original course, which opened in 1915, and 16 years later, Wayne Stiles remodeled it. Former Tom Doak associate and classic design expert Bruce Hepner has consulted with the club in recent years. It will host the Massachusetts Mid-Amateur Championship in 2027.
Wyantenuck Country Club (Great Barrington) - This private club's design history includes lesser-known architect Robert Pryde, who laid out its original golf course in 1913. A decade later, architect Charles Banks, who worked with C.B. Macdonald and Seth Raynor, renovated several holes after working with Raynor to build the course at the nearby Hotchkiss School in northwestern Connecticut. President Richard Nixon played some golf at Wyantenuck, as did Babe Ruth and boxing champ-turned-actor Rocky Graziano.
Stockbridge Golf Club (Stockbridge) - There are few places in America where a single winding river is more interwoven with a single golf course. The Housatonic River curlicues its way across the property, with holes playing up to, along and across it throughout the round. This is another private club, but it hosts multiple tournaments per year for which non-members may sign up.
3 more notes for Berkshires-bound golfers
1. Lodging options galore. There is no shortage of places to stay in one of the favorite summer destinations in the Northeast, from private rentals to standard hotels to any of dozens of quaint and often relatively affordable bed & breakfast-type setups. Big spenders bed down at places like the Miraval Berkshires or the famous Canyon Ranch, known as one of the world's best wellness retreats, with two Michelin Keys.
2. Better mid-week. The fact that several of the Berkshires' best golf courses are semi-private means that you will have an easier time securing the tee times you want if you visit during the week. Weekends can be tricky as members have the right of way.
3. Foliage for days. Like much of New England, the Berkshires come alive every fall when the deciduous trees turn from green to brilliant reds, oranges and yellows. If you come to play golf and leaf-peep, you might need to keep an extra-keen eye on errant shots that hide under fallen foliage.
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