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Living Big Travel Blog

Travel tips, guides, and real life stories to inspire your next adventure. Go explore! 

Day Trips from Portlandia


Portland will forever be my home. It’s the city I’ve lived in and worked in for most of my life. It’s the city that has welcomed me back from various corners of the world and kept me intrigued all these years with innovations in food, culture, new friends and beautiful natural sights. Ah….I love it.

But what makes me love Portland even more is the lifestyle it affords. Within a few hours drive from Portland I can be in a dramatically different community that offers new sights and activities. And the best part is that most of these places can be visited in a single day!

Well here it goes – from a native Portlander to you – my top day trips from Portland. You’ll notice there are consistent elements in each day that include a little adventure and activity and then food, drinks and a good time. Enjoy!

1. Oregon Coast – brunch, beach, hiking and beers


On my way out of town I would stop in downtown Portland for breakfast at Tasty & Alder. Early in the morning it’s generally pretty easy to park in this part of SW Portland and the food is downright yummy. I might even walk around the corner afterwards to grab a donut (you need energy for the road!) at Blue Star Donuts.

  • The drive to the coast from downtown Portland is an easy 90 minutes directly out Highway 26. I like to head towards Cannon Beach. When you get into this sleepy beach town grab a coffee at Insomnia Coffee Company then go straight to the beach. Nothing beats that first moment when you inhale the fresh ocean breeze with feel the sand between your toes!

  • Get back in the car and drive about 14 miles south and park in the Cape Falcon trailhead parking lot. Grab your backpack, hiking shoes, water and some snacks and start your hike on the Cape Falcon trail. Its about 5 miles roundtrip but the view at the end of the hike is worth it!

  • When you get back from the hike spend a few minutes cooling off in the Pacific Ocean at Oswald West State Park. You’ll see signs directing you to the beach as you get closer to the start of the trailhead.

  • When you’re ready for dinner drive about 8 miles south to Manzanita or 14 miles north to Cannon Beach. Find a pub or fine dining restaurant in either town and grab a table that faces the ocean so you can watch the sunset while enjoying your dinner with a local microbrew.

  • After dinner take another walk on the beach, build a beach fire (check local signage for rules) then make your way back home.

2. Sauvies Island – French pastries, biking, beach and berries


Load your car with your bike gear, a cooler full of beers (cans) and snacks then head towards the industrial corner of NW Portland. Make a pit-stop at St. Honore Boulangeri for coffee and the most amazing French breakfast and pastries. When you have had your fill head west towards St. Helens for about 25 minutes until you get to the bridge that takes you over to Sauvies Island.

  • Park your car in the parking lot that is just over the bridge and walk to the adjacent convenience store to pick-up a day pass for your car. Hop on your bikes and start enjoying the 12 mile bike loop that goes all around the island. The air is clear, the scenery is lovely and you’ll soon forget you’re only 30 minutes outside Portland!

  • After the ride get back in the car and drive north about 9 miles along Reeder Road for some R&R and beach time. Pick a spot anywhere on the beach to set-up camp. If you head too far down this road you’ll run into the nude beach. I prefer to be as close to the nude beach as possible (its quieter) but not actually on the nude beach. Lay in the sun, swim in the water, bring a grill to BBQ and enjoy the snacks and beer you packed.

  • When you’re ready to head out be sure to stop at Krugers Farm to stock-up on their hand-picked fruit and veggies. Check their website for event listings. They often host summer concerts and farm-to-table dinners.


3. Hood River – breakfast sammiches, small town strolling, picnic lunch, wine, beer and pizza


You’ll be heading east on I-84 to get to Hood River. On your way out of Portland stop by Pine State Biscuits on NE Alberta to fill your belly with their tasty southern breakfast sammiches. Pack your car with a small empty cooler. This will become very important later!

  • When you arrive in Hood River head to main street to visit the local shops, galleries and tasting rooms. While you’re walking around be on the look-out for snacks or a lunch you might want to buy and take on the next leg of your Hood River afternoon. I like the sandwiches, salads, meat and cheese at Boda’s Kitchen.

  • Its time to get in the car and head out on the ‘Fruit Loop,’ which is a 35 mile driving path that circles the greater Hood River area with stops at local wineries, fruit stands and other local businesses. Stop as many times as you like, and be sure to find a winery with a beautiful view and picnic area to enjoy your lunch with a bottle of the house wine.

  • When you have had your fill of wine head back into Hood River to visit Double Mountain. One of my favorite breweries with pizza that is almost as famous as its beer. Enjoy a cold IRA, a truffle-shuffle pizza and a relaxing evening. Check their website, as they often have live music playing in their adjacent event space.

4. Wine Country – ladies only day with road sodas, wine tasting, hiking, massages and dinner with the boys 


This day (ideal with girlfriends) requires a little advance planning. But it’s so worth it!

  • When your friends meet at your house in the morning have Giada’s Apricot Oatmeal bars(amazing) ready to eat along with fresh fruit, granola and yogurt. Make sure each (non-driving) friend leaves with a mimosa-filled sippy cup as you make your way 60 minutes outside Portland to the heart of Pinot Noir country.

  • Head towards Sokol Blosser Winery in Dundee to join for one of their annual wine hikes. Note: advance registration required. Book early in the year to reserve your space! You’ll hike through the Sokol Blosser vineyards with a wine maker as your guide learning about the grapes, harvest and wine-making process. And all the while sipping their wines that have been stashed within the vineyards. After a few hours of hiking you’ll end up at their tasting room for a beautiful lunch paired with their wines.

  • You’ll likely be tired after the hike, so book a massage at the beautiful Allison Inn & Spa. Head to the spa well before your scheduled appointment to enjoy their ladies-only waiting area that is both inside/outside. Oh and bring that magazine you’ve been dying to read. Its the perfect setting!

  • After the massages enjoy a dinner at the hotels restaurant, Jory, or head back to the city for dinner at Toro Bravo. There is always a long wait, so I suggest you invite the men in your life to join for dinner. But you might ask them to go early and put your name on the list

Looking for fun in Portland? Spend a few minutes reading My Portlandia: how to experience Portland like a local.