Travel east of Portland through the verdant landscape of Willamette Valley, known for its hazelnuts, berries, Christmas trees, and Pinot Noir. Stop at a donut shop in the town of Sandy for coffee and morning treats before beginning your ascent of Mount Hood, the highest summit in Oregon. Spend the next hour at the historic Timberline Lodge and enjoy 1 hour of free time.

From Timberline Lodge, head to Hood River Valley. Here, feed baby pygmy goats, get a photo of Mount Hood, purchase local fruit and preserves, taste cider, or buy a huckleberry milkshake. Afterwards, visit downtown Hood River and break for lunch. After lunch, learn about the geological history that shaped the Columbia River Gorge as you drive eastward past windsurfers in the Gorge, before stopping at a viewpoint to admire panoramic views of the Cascades.

Next, travel westward through the Columbia Gorge and stop at Multnomah Falls, the tallest waterfall in Oregon, where you can walk up to the Benson Bridge, visit the interpretive center, buy a snack, or peruse the gift shop before heading back to Portland.