If Oregon doesn’t sound exotic to you, well, it’s probably because you haven’t been there. The towering trees alone are enough to make you feel humble, and if you think Michigan’s beaches are stunning, wait until you see Oregon’s. Picture this: huge cliffs giving way to soft, sandy shores, and mountains rising up everywhere—one of them even blew its top in 1980.
I lived in Portland from 1995 to 1998, and every Saturday, I had to decide whether I wanted to:
- Head to the beach
- Go skiing
- Hike to a waterfall in the Columbia Gorge
- Or simply stay home and take a walk through Forest Park and marvel at the roses—yes, even in February.
Portland is a place where nothing really makes sense in the best possible way. Situated at the same latitude as Michigan, it’s temperate year-round—no snow in winter, and plenty of rain to keep everything lush. The city lies at the confluence of two rivers, the mighty Columbia and the Willamette (pronounced wil-LAM-ett). And while it’s about four times the size of Grand Rapids, it shares a similar vibe: a river running through it, a network of bridges, and the city divided into quadrants—NW, SW, NE, SE… you get the idea.
Despite the lack of snow, Portland is definitely a great place for ice skating. In fact, I was surprised to find ice skating rinks inside shopping malls—where Tonya Harding got her start, in case you didn’t know.
And let’s talk food. Portland is a foodie haven, but you don’t need to stress about finding the best place to eat—just about anywhere will blow your taste buds away. Think Paris, but with a more laid-back vibe. Portland’s craft beer scene is legendary, and much like Grand Rapids, it’s been driven by local pioneers. The McMenamin brothers, for example, have turned iconic old buildings into quirky brewpubs—places like the Baghdad Theatre, where you can sip a cold one and watch a movie. There’s also no shortage of ethnic cuisine, from Thai to Ethiopian, and the bakeries? They’re world-class. Rumor has it, it’s all thanks to the water, but whatever the reason, the pastries are perfection.
But here’s the thing: the most spectacular part of Portland isn’t the city itself—it’s everything around it.
A Must-Do Circle Tour: Portland to Mount Hood, Hood River, and the Columbia Gorge
From downtown Portland, head east toward Mount Hood—this towering beauty looms over the city like a silent guardian. Depending on the weather, it can either seem massive, with water vapor distorting its size, or tiny, with only the white tip of its peak visible in the distance. Mount Hood is a glacier-capped mountain that’s always snow-covered, and if you’re visiting in winter, don’t forget to pack chains for your tires. It’s only about a 45-minute drive to the Timberline Lodge, but once you’re up there, you’ll be greeted with views so stunning, you’ll feel like you’ve entered a snow globe. (And yes, if you’re a fan of The Shining, you’ll recognize the exterior of the lodge. No maze though—sorry, folks.)
After soaking in the views, head into Hood River, a charming little town that’s perfect for grabbing a bite or just wandering around. If you’re up for some skiing, Mount Hood offers slopes almost year-round, though I’ll be honest—it’s not the best skiing experience. The snow gets a little blinding and monotonous, and beyond 6,000 feet, there’s nothing but white and more white. Still, it’s worth trying if you want to say you skied on an active volcano.
The Columbia Gorge is another must-see. After Hood River, swing by Bonneville Dam and check out the fish, or take a scenic detour to Multnomah Falls. There are a number of hikes in the area—Eagle Creek Trail comes to mind—that will lead you to some of the most jaw-dropping waterfalls you’ve ever seen. But fair warning: the trails can be steep, so make sure you’re prepared for a little adventure. If you’re pressed for time, you can easily make a day of it.
But if you have more time, consider staying at Timberline Lodge and saving the Columbia River Gorge for the next day. Then, after all that hiking, take a well-deserved break in Portland, eating your fill of incredible food before heading to the coast.
A Trip to the Oregon Coast
Now, no trip to Oregon is complete without experiencing its breathtaking coast. Cannon Beach is a must-see, especially if you want to get up close and personal with Haystack Rock. Or, if you’re feeling cheesy (no pun intended), head to the Tillamook Cheese Factory, where you can indulge in some of the best dairy products on the planet. Afterward, take a short drive to Manzanita—my personal favorite. Explore the tide pools or, if you’re there in the winter, head to the cliffs for some whale watching.
There’s so much to see and do in Oregon that I would highly recommend staying for a while—like I did, for three years. You won’t regret it.
Pro Tip: You can’t forget your rain gear. Seriously. Bring it.
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