Oregon's Willamette Valley cuts a broad green swath through the state, between the snow-capped Cascades to the east and the cloud-blanketed Pacific Coast Range to the west. The fertile soils and gentle hillsides of the region (the heart of which lies less than an hour southwest of Portland) create the perfect canvas for two things: grapes and golf. Wine experts widely agree that Willamette (pronounced wuh-LAM-it), with its cool climate and mixture of coastal and volcanic soils, is one of the world's best places for producing pinot noir. As for golf, there is plenty to choose from, including Pumpkin Ridge, which in August hosted the U.S. Women's Amateur, and the Reserve, the annual site of the Champions Tour's Jeld-Wen Tradition.
When you come to the valley, be a little patient with the local rules and regulations—they're designed to keep development at bay. For example, all inns in the area (with one exception) must have no more than nine guest rooms, and none are permitted to serve lunch or dinner. But you'll find the people here welcoming all the same. Though they may be busy working the vineyards—October is harvest season—these small vintners still follow old-fashioned rural etiquette: They're homespun, charming and always hospitable.
The best way to get here is either via a commercial flight into Portland International Airport or by private plane into Hillsboro Airport, a smaller airfield that serves executives at Nike and Intel and is just five minutes from the Reserve Vineyards & Golf Club, the first stop on this trip. (If you're flying into Portland, you'll have a forty-five-minute drive to the club.)
The Reserve has two championship courses. Play the South, designed by John Fought and the stronger of the two. The layout demands accuracy, thanks to its 113 bunkers—including an eye-popping sixteen on the par-five sixth hole. Be sure to steer clear of the pot bunker guarding the double green at eleven and seventeen.
Afterward, have a cold drink in the chateau–style clubhouse and head south into the hamlet of Carlton. In less than ten minutes you'll have left civilization behind—the landscape is all rolling hills, farms and forests, and vineyard upon vineyard. Spend the night at the Abbey Road Farm Bed & Breakfast, which has been fashioned from converted grain silos. For dinner, try Cuvee, a charming country French restaurant.
Wake up to the aroma of fresh-brewed coffee and breakfast prepared by your hosts, John and Judi Stuart. The couple will happily draw up a list of wineries for you to visit, and they'll insist that you take a button of their homemade goat cheese as a gift.
But first things first: Jump in the car and drive thirty minutes to Pumpkin Ridge Golf Club. Just fourteen years old, the club has already secured a place in golf history, most famously as the stage of Tiger Woods's third consecutive U.S. Amateur victory (in 1996). It has thirty-six holes: the private Witch Hollow and the semiprivate Ghost Creek, both laid out by Bob Cupp and defined by native firs and swaying fescue. It's a matter of opinion as to which is better, but if you want to see where history was made and you're a member of a private club, call ahead to ask for a tee time at Witch Hollow.