Match the road to the ride
Skyline Drive | Ford Flex ($30,885)
This 105-mile road through the Blue Ridge Mountains of Virginia extends the entire length of Shenandoah National Park, alternately tunneling through dense trees, then breaking out into breathtaking vistas. During the foliage season (usually late October to early November) it's particularly crowded, but also particularly gorgeous. Be prepared to brake for animals; the park has white-tailed deer, black bears, turkeys and all kinds of other critters that like to cross the road.
The speed limit in Shenandoah is 35 mph and it's strictly enforced, so you can leave your sports cars at home. But Skyline Drive is the perfect family road trip. So we recommend a perfect family vehicle. The Ford Flex is cavernous, with three rows of seating for seven passengers, and if you get the optional multipaneled Vista roof, this thing is all windows, giving passengers generous views of the Virginia mountains. A 3.5-liter 285-horsepower V6 engine is standard, but if you can swing it, get the EcoBoost engine that adds a turbocharger and bumps up the horsepower to 355, yet keeps the full-size crossover's mileage in the high-teens to mid-20s.
Portland to Bend, Ore. | Jeep Grand Cherokee ($26,995)
It's not a particularly challenging drive, but few parts of America can match the staggering variety of scenery and activity available in this 3.5-hour drive. Load up your camping and fishing gear and head east from Portland on Route 26 toward Mount Hood. As you climb into the Cascades, open the windows and sunroof and you'll get hit by a blast of pure oxygen. Continue along Route 26 and marvel at Oregon's largest volcano as you pass by. Then watch the dense, lush forest give way to high desert on the other side of the Cascades. At Madras, switch to Route 97 all the way into Bend. The Bend area is home to some of the American West's best fishing and camping spots, or use it as the jumping-off point for another great drive to Crater Lake, two hours to the southeast.
For this type of trip, you're going to want to pack a lot of gear and stay awhile. Plus, the roads in the high desert can turn to dirt unexpectedly, so it helps to have a vehicle that drives well in the dust and gravel. If you can afford it, bump up to the Grand Cherokee Limited 4X4 ($39,295) with the cushy leather seats, 506-watt stereo and panoramic sunroof to let in that intoxicating mountain air.
Sam Foley is a Connecticut-based automotive journalist who has written for GQ, Forbes, USA Today, the New York Post and various other publications.
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Why stop at Silverton? Go all the way from Ouray to Durango. Get some great Mexican food for lunch and then return to Ouray for dinner.
What a GREAT day that would be!