How to Explore Portland in Five Days

This is my suggested itinerary for someone who has five days to spend in Portland, Oregon. You only need a rental car for two of these days.

Day 1

Settle in to your hotel and get a feel for the city. Ride MAX and the street cars if you don’t have a rental car, or rent some bikes. Your hotel will either have bikes or a connection to a rental shop. If they don’t, almost every bike shop in downtown does rentals. There is a big one down by Saturday Market that does mostly rentals. Visit Powell’s, any of the Food Carts, Saturday Market if you’re here on a weekend. Have dinner at Andina, Oba!, Biwa, Toro Bravo, Urban Fondue or any thing else that sounds good. Hit up VooDoo or Blue Star Donuts. Walk that off by going to Salt and Straw Ice Cream. Walk that off by any brew pub around you come across.

Day 2

Head to the Columbia River Gorge. Just after Troutdale be sure to follow the signs for the Historic Columbia River Highway and follow the signs to Vista House and Multnomah Falls. If you are there on Sunday, do the Brunch at Multnomah Falls Lodge. There are seven falls that are easily accessible from the old highway, but the parking areas sneak up on you so be careful through there. If you have the time you should at least walk up to the top of Multnomah Falls. The Gorge is also full about a hundred miles worth of trails so you could easily spend your entire five days here and only see a small part of it. There are entire websites dedicated to Waterfalls in the Gorge, and Hiking Trails.

Personally I’d continue down the Historic Highway until it merges back with I-84. There is a little jog to your right that continues to follow the old highway further and leads to campgrounds, more falls and more trails. The most interesting one, if you really want to go that way, is “Hole in the Wall” Falls, formerly Warren Creek.

You should try to head into Hood River and have dinner there, or Wine Tasting in town. The Hood River Fruit Loop is fun and could take a day by itself. This is a series of independent farmers fruit stands, coupled with about a dozen Wineries. The best time of year is the fall when the pears and apples are ripening, but it’s a fun drive no matter what time of the year it is. If you’re feeling really sadistic, or it’s early enough, you can continue around past the South side of Mount Hood to link back up with Highway 26 and then circle back into Portland via Sandy and Gresham. This is a gorgeous drive no matter what time of the year, but does get snow and ice in the winter around Mt. Hood. You can stop at Timberline Lodge for dinner or overnight.

Day 3

Day three, if you didn’t spend it all in Hood River should include the Oregon Coast. Depending on exactly what you want to see and how much time you have, there are three major loops you can take. Portland – Astoria – Seaside/Cannon Beach – Hillsboro is one. Portland – McMinnville – Lincoln City – Newport – Salem, or a combination of the two which includes driving between Newport and Astoria and looping back. I’d probably stay with the Astoria, Seaside, Cannon Beach route.

There are a ton of things to see, a couple of websites are dedicated to movie locations in that area including Goonies, Short Circuit, and Kindergarten Cop. You can go out to Fort Stevens and see the wreck of the Peter Iredale. You can also cross the Astoria-Megler bridge and go up to Long Beach and see Marsh’s Free Museum and Jake the Crocodile Man.

In the interest of space, I’m skipping a lot you can see on all three of these loops. Any of these could be a full five day trip in themselves though.

Day 4

Stay in Portland, visit the Rose Gardens, Japanese Gardens, Chinese Gardens, and Rhododendron Gardens. Pick a different area of Food Carts and have lunch there. Do a little shopping at Pioneer Place.

Day 5

Vist the Oregon Zoo, OMSI, Oregon History Museum, Portland Art Museum and the Oregon Rail Heritage Center.