The European settlers and fortune-seekers who made their way West along the Oregon Trail in the mid-19th century faced a difficult choice when they arrived at the steep valley known today as the Columbia River Gorge—the only sea-level pass through the north-south Cascade mountain range. They could try to float their wagons and possessions down the river on rafts through dangerous rapids. Or they could attempt the overland route through the Cascade mountains on the Barlow Road, a dirt track so steep that it could only be traversed with great difficulty. Some intrepid Barlow Road travelers resorted to cutting down trees and lashing them to the backs of the wagons to slow their descent. The good news: The scenery in the Columbia River Gorge and the Cascade Range are just as spectacular today, but the roads have improved considerably.

Overview
Drivers can get an excellent sense of the history, beauty, and diverse charms of the Columbia River Gorge region by starting in Portland and tracing a roughly triangular route east alongside the Columbia River, south up the slopes of Mount Hood, and then back west following the Sandy River through a picturesque landscape of small villages.

Start in Portland
Oregon's largest and most popular city offers everything from green parks and gardens to bookstores, galleries, and an abundance of innovative eateries. Indeed, the city's innovative spirit is noticeable to the most transient visitor. "With all the creative people who have lived and still reside here—people like director Gus Van Sant and writer Ursula Le Guin—the city's neighborly Midwest vibe has a cosmopolitan edge," says Thomas Lauderdale, leader of the local band Pink Martini. The city is worth at least a day of exploration before starting the drive. When you're ready, take Interstate 84, the quickest and most convenient route, out of the city.