The Ultimate 4-Day Road Trip from Portland: Explore the Columbia River Gorge, Mt. Hood Scenic Byway, and Oregon Trail (2024)

One of my favorite summer road trips is to make an easy driving loop out of Portland through the Columbia River Gorge and around Mt. Hood. The trip takes you on the Mount Hood Scenic Byway, past Oregon's tallest peak, the snow-capped Mt. Hood, and along the final portion of the historic Oregon Trail. Although you can drive the entire 105-mile route in under four hours, it's best to savor the journey over four days, immersing yourself in the beauty of the Pacific Northwest and partaking in adventures from waterfall hikes to wine tasting.

Day 1: Dive into Portland's Eclectic Culture

Start your adventure in Portland, known for its diverse arts, music, culinary, and outdoor scenes. Set against the backdrop of Mt. Hood, Portland’s historic West End is a hub of creativity, fashion, and nightlife. Don't miss Powell’s City of Books, the largest bookstore in the world, spanning an entire city block with over a million volumes.

Stay at The Nines, a luxury hotel next to Portland’s Pioneer Square. Housed in the historic Meier & Frank Building, this hotel features striking décor and an impressive contemporary art collection. Enjoy city and Willamette River views from the rooftop bar or dine at the Departure Restaurant, which serves modern Asian fare with a Pacific Northwest twist.

For a memorable dining experience, visit Scotch Lodge, a speakeasy with a modern French menu. Start with the oysters served with three types of granitas, followed by the arancini appetizer. The duck breast pappardelle pasta is a popular entrée choice, complemented by a craft co*cktail from their whiskey-focused bar. Other notable restaurants include Le Pigeon, known for its innovative French cuisine, and Tasty n Alder, offering a globally influenced menu with local ingredients.

Days 2 & 3: Explore the Columbia River Gorge

From Portland, take I-84 east towards Hood River to explore the Columbia River Gorge, the largest National Scenic Area in the US. The area is renowned for its breathtaking waterfalls, like Multnomah Falls, the tallest waterfall in Oregon, with a total drop of 620 feet. It is one of the most visited natural attractions in the Pacific Northwest.

The falls are easily accessible from Interstate 84. There is a parking lot specifically for Multnomah Falls visitors. It's a short, paved walk from the parking area to the viewing area at the base of the falls. For a more immersive experience, hike the 1.2-mile trail to Benson Bridge, which spans the first tier of the falls, and continue up a series of switchbacks to the top for panoramic views of the Columbia River Gorge.

Other excellent hikes in this area include the Eagle Creek Trail to Punchbowl Falls, a 4.2-mile round trip through lush forests to a pretty waterfall. For a more challenging hike, try the Dog Mountain Trail, a 6.9-mile loop with steep climbs but rewarding panoramic views.

The area is also home to around 50 wineries and 90 vineyards. Located in Hood River, Hiyu Wine Farm is known for its organic wines and farm-to-table dining experience. Their small-batch wines reflect the region's unique terroir, and you can book a wine farmers lunch, which pairs their wines with farm-to-table fare. Cathedral Ridge Winery, also in Hood River, is celebrated for its award-winning Zinfandel and Syrah varietals. You can do vineyard tours and guided tastings here.

Spend the night at Sakura Ridge, a luxury five-room bed and breakfast on a working farm and orchard in Hood River. Recently renovated and owned by Nashi Orchards, this B&B offers fantastic views and exceptional breakfasts. It is also known for its cider, produced from fruits grown in its orchards.

Day 4: Explore the Mt. Hood Area

Drive towards Mt. Hood via Hwy 35 and then head west on Hwy 26, the last segment of the Oregon Trail used by pioneers in the mid-1800s. The journey features mossy green rainforests, snowy mountains, and rushing waterfalls. The Mt. Hood area is a paradise for outdoor enthusiasts with excellent hiking trails.

Check out the Mirror Lake Trail, a 4.4-mile round trip offering stunning views of Mt. Hood reflected in the lake, or the Ramona Falls Trail, a 7-mile loop that takes you to a beautiful cascading waterfall. Don't miss the Trillium Lake Loop, a 2-mile easy hike with breathtaking views of Mt. Hood.

Stay at the historic Timberline Lodge, built in 1936 and a National Historic Landmark. Known for North America's longest ski season, this lodge offers cozy rooms, a pub, a restaurant, and residents St. Bernards, Bruno, and Heidi. In summer, there is plenty to keep you entertained. One of the most popular summer activities is riding the Magic Mile Chair Lift to the mountain top. The spectacular view of Mt. Hood, Palmer Snowfield, and nearby Mt. Jefferson is gorgeous.