By far the most popular day trip from Portland  is the so-called Mount Hood Loop, which connects many of the sights in the Columbia River Gorge  into a single day’s driving adventure. Depending on side trips, the loop is about 160 miles in length — not too stressful if you get an early start and make frequent stops.
Of course, the loop can be driven in either direction, but it’s common to begin by driving I-84 up the Columbia River Gorge, detouring onto U.S. 30, the Historic Columbia River Highway , which passes towering waterfalls and hiking trailheads — you should definitely make time for a short walk to an otherwise hidden waterfall to appreciate the gorge’s striking natural history.
After spending the morning in the mists of waterfalls, continue to Hood River  for lunch. From here, head south on Highway 35 through orchards and farmland toward Mount Hood , which by this time will be filling the horizon. In summer and fall, this road is lined with farm stands selling fruit and vegetables.
At Mount Hood, drive up to Timberline Lodge  to go eye-to-eye with the mountain, Oregon ’s highest at 11,239 feet. Have a hot chocolate in the historic lodge, and take a short hike around the base of the ski lifts (chances are you will be huffing due to the elevation).
Then drop down the west face of Mount Hood on U.S. 26, following signs in Gresham, Portland’s most eastern suburb, back to I-84 and Portland .