How to Spend Four Days in Oregon: Coast, Waterfalls, and Wine Trail
What to do with a four day trip to Oregon? If you are flying into Portland there are some obvious places to start: The coast. The Columbia River Gorge to Hood River. Williamette Valley. Bend. Portland day trips. So much to do and see! After a ton of research and an awesome trip, I suggest your four day Oregon itinerary includes the Oregon coast paired with one inland spot. We picked Cannon Beach and the Hood River area and I highly recommend this combination for some dramatic coastal exploration, various hiking terrains, a lot of waterfalls, and wineries + breweries + cider tastings.
FITZ BITS TIP: Consider off-site car rental locations if you find the Portland Airport rentals to be overly expensive. We found a small SUV for half the price at the Enterprise in Vancouver, Washington. Even with $20 – 25 Uber rides in both directions, we saved a total of over $200.
These are my honest opinions and recommendations — I do not receive any compensation or discounts during our travel. This story does include some affiliate links for which I may receive a small commission at no extra cost to you. Please click the links to support my blog.
Lodging Information
Cannon Beach, Oregon (2 nights)
It is hard to beat the three-star Hallmark Resort Hotel and Spa for the beachfront location and proximity to Haystack Rock. An Ocean View Room was not available during our stay, but if you can snag one of these rooms it could be worth the splurge.
I read some mixed reviews, but the hotel and front desk staff at the Hallmark Resort far exceeded my expectations. We also really liked the freshly baked cookies from 4-6 PM, the in-room gas fireplace, and the two hot tubs + sauna at night! Also, you can purchase a bonfire kit at the front desk, with or without s’mores, that includes an easy starter brick for a beach bonfire. How fun!
Hood River, Oregon (2 nights)
The Best Western Plus Hood River Inn was a surprising little gem! Or, actually a big gem. This hotel is huge. It has a lot of amenities including a full restaurant, bar, outside patio, outdoor heated pool and hot tub, and fitness center with an indoor hot tub and sauna. All stretched out alongside the scenic Columbia River.
While our room was quite basic, and a bit musty when we walked in, the balcony and amenities made up for it. If you stay here be sure to get a Riverside Room — and, enjoy a cup of coffee or a glass of wine out on that balcony!
FITZ BITS TIP: I found the Best Western’s weekday rate to be about half of the weekend price. So, consider this when creating your itinerary.
Day 1 | Explore the Oregon Coast
Choose your adventure: explore north or south of Cannon Beach
You will do less driving if you spend the day exploring the coast on your way in to Cannon Beach. Start in either Tillamook from the south or Astoria to the north. With only four days in Oregon you will not have time to do both drives without rushing the experience and spending a lot of your precious vacation time in the car.
Check the weather radar for rain because this may make your decision easier! Save the areas that are closer to Cannon Beach for the next day.
North from Tillamook
Rain was forecasted for mid-afternoon so we skipped Tillamook Creamery in order to get time on the coast before it disappeared into the fog. This is typical in Oregon and with proper rain gear inclement weather doesn’t have to slow you down.
- Tillamook Creamery
- Three Capes Scenic Loop: We went to Cape Lookout, but drive as little or far as you like
- Oceanside Beach: At low tide, walk to the northern man-made tunnel to the secluded Tunnel Beach — note the fallen rock warning sign
- Cape Mears: Lighthouse, Octopus Tree, Sitka Spruce, Beach Trail with a rope to descend to the beach
South from Astoria
We did not take this route, but here is what I would have wanted to see and do. There is also Lewis and Clark’s Fort Clatsop, but that didn’t make my list.
- Astoria: Column, Astoria-Megler Bridge, Goonies houses
- Fort Stevens State Park: Hiking, military sites, beach shipwreck photos
- Sunset Beach Trailhead
- Seaside Promenade
Arrive at Cannon Beach to see Haystack Rock at low tide
Try to be back in Cannon Beach for the evening low tide so you can explore the tidal pools and take some awesome photos of Haystack Rock. Photography Note: Take some photos with someone or something in the frame so you can see the massive size of these formations.
Day 2 | Cannon Beach Area
More Haystack Rock
Get the know the tide table because you really should explore Haystack Rock again at low tide if you didn’t see the sea stars yet. Apparently the tide went out a bit further in the morning so we found sea stars of varying colors on the rocks to the north side of the Haystack.
Ecola State Park
There are many trails and beaches to explore. There are also signs showing where films such as Goonies and Point Break were filmed. So fun!
Devils Cauldron and Short Sand Beach
These are two great destinations just a short drive south of Cannon Beach. You get to Devils Cauldron by hiking down from the Elk Flats Trail parking lot. Continue hiking to Short Sand Beach from here, or drive back north towards Cannon Beach to the next parking lot for a quick hike to the very picturesque Short Sand Beach. There are two paths to the beach because of a river down the middle: Short Sands Trailhead or Cape Falcon Trailhead. From the Short Sands Trailhead you can explore some pretty cool tidal pools to the left
The resident elk
There are herds of elk in the Cannon Beach area and it is fun to spot them! The elk hang out in green spaces such as the Lyngate Park where we found this guy.
Day 3 | Scenic Drive to Hood River
The Scenic Columbia River Gorge Byway
You can start this scenic drive from Exit 17 Troutdale or Exit 22. There are signs explaining this historic drive that was built in the New Era. It is really fun to jump out at the various interest points and waterfalls along the drive. Folks move on, so be patient if you do not see a parking spot right away. Note: depending on the time of year you may need a timed ticket for the Multnomah Falls.
Save some time for the Bonneville Dam to learn about this engineering feat and see the fish swimming through the steps.
Hiyu Wine Tasting in Hood River
We usually do the standard wine tasting, but Hiyu’s small plate pairing with the wine tasting made for a special experience. What a beautiful setting inside and out! You can also explore their garden before or after your tasting.
Dinnertime
Based on this itinerary you will have two nights in Hood River. I suggest dining in Hood River one night and across the bridge in White Salmon on night two.
Day 4 | Exploring the Hood River Area
Catherine Creek Trail System to the Coyote Wall
Maybe it was because we finally had great weather, but was our favorite hike! You are rewarded with beautiful views of the Columbia River and Mount Hood most of this hike. It took about two-hours roundtrip including a quick climb up the Coyote Wall. You can continue hiking from there, but we wanted to get to a wine tasting and some more hikes. Start by walking along the water to the Moab Trail. This will take you to the Coyote Wall where you can loop back down on the Maui Trail. The trail is easy to find and track on AllTrails. Note: There is no shade.
The Fruit Loop Trail
There are many wineries and stops along the 35-mile Fruit Loop Trail just south of Hood River. I originally wanted to rent e-bikes for the Fruit Loop Trail, but the main roads are too busy and narrow. If you want to do an e-bike experience I highly recommend you take a tour where they know the side streets.
Make your first wine tasting when a vineyard opens. Ask if you can walk along the vines and taste the grapes. We stopped at Hood River Winery for a tasting with spectacular views of Mount Hood. Boisenberry milk shake at Orchard Bakery. Cider at Cider Girls. And then made our way to a hike.
Tamanawas Falls Hike
A pretty easy, mostly shaded hike to a beautiful waterfall. Even though you likely saw and hiked to several waterfalls along the Columbia River Scenic Highway, this is unique because you can hike behind the falls! The trailhead is about 30-minutes south of Hood River, but we broke it up with stops along the Fruit Trail on the way there and back. This is a good add-on if you are looking for another hike, but I would not say it is a must-do. If you are looking for one great hike I would recommend the previously mentioned Coyote Wall.
Visited in September 2021
