Timberline Lodge

I created this guide for the Airbnb "Hillside Getaway" (link below) with food and outdoor enthusiasts in mind and those wanting to experience the cultural side of Portland. Although my childhood hometown has changed a lot over the years, Portland is still the vibrant, artsy, cultured city I've always known. The "Rose City" has so much to offer—a great food and music scene, the outdoors, and an independent spirit—surrounded by forests and set between two rivers, the peaks of the Cascades, and the Pacific Ocean. This environmentally conscious city has a good rail system with miles of bike paths and walking trails. Virtual explorers and trip planners alike, explore Portland with this interactive guide. Check out what to SEE + DO, places to DRIVE + RIDE, and where to EAT + DRINK around this river city in the northwestern corner of Oregon. This list is far from exhausted and will continue to expand. Click places and links to learn more. Note: When you click and buy through links in this guide, we may earn an affiliate commission at no extra cost to you. To help fund production of these guides, tips are highly appreciated.

Itinerary ideas for you to explore. In most cases, I would suggest a minimum of 2 nights at each location, so depending on your timeline you may want to eliminate a few destinations.

Oregon is a big and beautiful state for outdoor enthusiasts. I got just a small taste when I visited NW Oregon for a long weekend in October. The weather was perfect, the amount of waterfalls left me speechless, and the coastline was out of this world. I spent 4 full days exploring and put a lot of miles on the rental car! Beginning and ending in Portland, I explored Mt Hood, the Columbia River Gorge Highway, and the coast. Save yourself hours of planning and use this adventurous itinerary for a solo, family, couples, or friends trip.