I didn’t know—a quiet and dignified man, he’d never mentioned it. By the time I was a guest at his little inn, Mr. Fran Waterman had Parkinson’s. He once asked me to help him close up his summer home near Castleton, and I’ll never forget making that drive—his hands shook so badly he could barely keep the car on the road.

That same drive west on Route 4, from Rutland to the tiny, quaint town of Castleton, is alive with color each fall, as if the richest memories have been squeezed from the landscape just before the cold descends. If someone in your party desires a side trip purely devoted to leaf-peeping, send them down that brief detour. And suggest they time the trip so that they stop for the chicken Philly wrap with iced coffee, followed by a slice of homemade pie, at Castleton’s classic Birdseye Diner.

The place to stay hereabouts, hands-down, is 40 minutes south of the Birdseye at an old pearl called The Equinox in Manchester Village. There is something reliably reassuring about Manchester Village—perhaps it’s the Carthusian monastery on top of Mt. Equinox, the worn white marble sidewalks or the way bright leaves sweeten the valley’s autumn air. With its fine Northshire Bookshop—for the best of Vermont writing, check out the novels of Craig Nova and Howard Frank Mosher, or Steven Cramer’s poetry—a slew of high-end outlet stores and hills peopled by the rich and famous, Manchester rivals Nantucket and the Berkshires as New England’s place to be. The Equinox has a modern spa, broad porches and sitting rooms in abundance, and a classy-casual restaurant that serves up fresh seafood and great steaks. This enormous, colonnaded hotel used to be owned by the Orvis family, and today you’ll find all the fly-fishing gear you could ever need at the Orvis store just up the road.

Gleneagles, the golf course at The Equinox, sits in a fertile bowl formed by the Taconic and Green mountain ranges. Its silky fairways and  gentle putting surfaces won’t challenge longer hitters the way a course like Green Mountain will, or satisfy shotmakers à la Rutland, but the last two holes can hold their own against any pair of finishers in New England. Playing No. 18 from the tips, you must hit at least a 260-yard drive over a tall maple tree (a little twinge in the back here as I attempted this) and across a long stretch of rough to a skinny fairway. That task accomplished, you are left with an uphill mid-iron to a green that has O.B. right and a deep long bunker left.

The Equinox offers a hearty morning meal, but I prefer to stop for coffee and eggs at a little hole-in-the-wall called Up For Breakfast. It’s just a handful of tables squeezed into a second-floor room, but the menu is extensive and the food superb. Soothed and sated, you’re now ready to make the scenic drive south on historic Route 7A. In less than an hour you’ll cross into Massachusetts’ Berkshire County and find another Stiles and Van Kleek emerald, Taconic Golf Club in Williamstown.

Owned by Williams College, Taconic is consistently ranked first or second in surveys of public-access New England courses. As with Rutland, its steeply canted greens can be frighteningly fast, but here the rough is deep and the par-4s lengthy. Walk to the back of the 14th tee and you’ll see a stone plaque commemorating an ace that some young fellow named Jack Nicklaus made here in 1956.

My wife and I moved to Williamstown when we were first married, not because we had jobs there—we didn’t—but because we liked the way the hills rose up around the small town. I found work as a housepainter here and was trying to get a writing career off the ground when I got the news that my dad had died suddenly. Amanda waitressed at first, then tended bar, and finally landed a photographer job at one of my favorite places in Berkshire County, the Clark Art Institute. The Clark, it so happens, sits across from Taconic’s second green, and guards within its collection a painting I never tired of gazing at, Bougereau’s “Nymphs and Satyr.” Singer Sewing Machine heirs Sterling and Francine Clark moved their extensive collection of Monets and Sargents here from New York City in the era when Manhattanites openly worried about a Soviet nuclear missile strike.

My friend Darra Goldstein, a Williams professor and internationally admired cookbook author, knows these parts well. She recommends dinner at Mezze for those who like hip bistro cuisine, and Mill on the Floss for classic French provincial. A few miles from Taconic is The Orchards Hotel, where film stars hide out during their visits to the Williamstown summer theater festival. Be sure to check out the wine cellar and sample the prize-winning cuisine of chef Swen Boehm.

This golf pilgrimage I’ve described saves its best for last. The Crumpin-Fox Club in Bernardston, Mass., 75 minutes east of Taconic, does not have an elegant clubhouse, celebrity members or shoppes across the street. This place is about pure golf, and if the relatively short venues at Rutland, Gleneagles and Taconic have left your driver feeling underappreciated, request permission to play the back tees, which measure 7,007 yards and rate a hefty 141 slope.

“Crump,” as the locals call it, is beautifully groomed, persistently unforgiving and, in all seasons, a joy to behold. Designer Roger Rulewich’s signature hole is the 592-yard eighth, where I once carded a 4 and many times wrote down an X. Playing from an elevated tee, with dense woods on the right and a pond all the way down the left, all you have to do is strike a long, straight drive, followed by a long, straight second shot and then a perfect wedge over water to a two-tier green.

Not long ago I took our oldest daughter, who is 7, up to Crump, where I played from the blues and she played from the 100-yard markers. On the relatively easy uphill second, she landed in a deep bunker, but insisted on playing the ball as it lay. When she blasted it out onto the green (with an improbable bit of backspin), I felt like a huge part of my wandering life had come full circle.

I finished this particular foliage trip half an hour south of Crumpin-Fox, in the bustling town of Northampton, home to the classy Hotel Northampton and a palette of eateries to rival a city 10 times its size—everything from Tibetan, Moroccan and Thai to Indian, Italian and Japanese. In Northampton, art movie houses, live music and bookstores mix with fancy clothing stores and gift shops. Stroll the broad main street on a fall evening, remembering your best shots of the trip and the big moments in your life, and you might come to have a special place in your heart for this colorful region, too.