Oregon is a magical place year-round, but, in our opinion, there is no better time to explore the state’s beauty than during the early fall.
During the months of September and October, the days start to grow cooler, the vine maples that line the roads throughout western Oregon begin to change to a vibrant display of reds, oranges, and yellows, and orchards come to life with the region’s famous apple and pear crops.
One of the best ways to explore the best of what Oregon has to offer during this magical season is to head out on a drive that begins and ends in Portland and takes you around the state’s tallest mountain, through the fruit loop, and past the gorgeous Columbia River Gorge and its jaw-dropping waterfalls.
You can easily do this drive in a day, but if you want to really relax and immerse yourself in the sights along the way, we recommend making a weekend of it with a stopover in Hood River.
Kick Off the Drive in Portland
Our trip starts off in the stunning city of Portland and takes you out Highway 26 towards the imposing peak of Mt. Hood. I
If you’re in need of some mid-drive food, then make sure to stop by Joe’s Donut Shop in Sandy. This red-and-white checkered building has been serving up tasty donuts and breakfast sandwiches to hikers, skiers, and adventurers on their way to Mt. Hood for decades.
Within an hour, you’ll find yourself passing through the mountain town of Government Camp. There are plenty of things to do here, including hiking to Mirror Lake or exploring the town’s restaurants (if you need some lunch, swing by Mt. Hood Brewing), shops, and museum, but for today, we’re going to be passing through.
The first destination is a lake with a jaw-dropping view of the mountain just a few minutes past town.
Trillium Lake
Trillium Lake is a popular destination for hikers, photographers, and campers for its easy access and stunning views of the mountain reflected in this scenic lake. During the fall months, the shores of the lake burst with color, making the view of the mountain all the more magical.
Driving Around Mt. Hood
From Trillium Lake, the road curves around and behind Mt. Hood. Along this road, you’ll pass by rivers cascading down from the glaciers above, miles of colorful foliage along the roadway, and plenty of places to stop and stretch your legs or head out on a short hike.
If your trip includes a night in Hood River, you’ll have time to visit the little-known but absolutely stunning Tamanawas Falls.
A 3.4-mile trail leads hikers through the forest and along a tranquil mountain river until dead-ending in a small amphitheater that showcases this magical waterfall. Adventurous hikers can brave the slick, mossy rocks to make their way behind the waterfall, where they can listen to the roar of the river as it passes directly overhead.
Picking Your Way Through the Fruit Loop
Shortly after the waterfall, the landscape will be to transition from mountains to fertile, rolling hills. Here the roadsides are dominated not by wilderness but instead by miles of apple and pear orchards.
This area is known as the fruit loop and is home to some of the most scenic (and delicious!) orchards you’ll find anywhere in the country.
Mt. View Orchards
A few miles west of the highway sits Mt. View Orchards. Here, you’ll find a winery, brewery, apple and pear orchards, flowers, pumpkins, and everything else that makes this stunning area such a delight to visit.
Grab a wagon and head out into the trees to pick your own selection of apples and pears or just grab from the selection that sits out front of the checkout area.
You can also sit and enjoy a picnic at their plentiful outdoor tables while enjoying a glass of their locally brewed beer or wine. The view of Mt. Hood standing tall over the valley only adds to the magic of this stop.
Stop Over in Hood River
Only 25 minutes past the orchard, you’ll pull into the scenic riverfront town of Hood River. This outdoor lover’s paradise is home to a wonderful selection of restaurants, breweries, and wineries and is the perfect place to spend an hour or a day.
If you spend the night in Hood River, make sure to stop by Pine Street Bakery on the way out of town to load up on sandwiches and cinnamon rolls for the road.
If you’re just passing through, then you can’t miss with a pizza from Double Mountain Brewing (although expect a wait on busy fall weekends).
Exploring the Gorge
The last stretch of the drive is arguably also the most scenic. And one of the best parts about making this drive in the fall is that permits are no longer required to stop at Oregon’s most famous natural landmark, Multnomah Falls.
Along this stretch, you can make your trip as long or as short as you want, as there is no shortage of waterfalls directly off the highway, like Multnomah Falls, or you can head off on a hike to explore the waterfalls that are tucked away within the cliffs of the gorge.
Once you’ve had your fill of sheer cliffs, river views, and cascading waterfalls, it’s time to head back into Portland to finish off the loop.
