The Perfect 5-Day Oregon Itinerary | Simply Wander (2024)

Oregon has so much to offer with stunning waterfalls, rugged coastlines, farm-fresh produce, forest hikes, city life, and much more. This 5-day Oregon itinerary will help you discover the best things to do in Oregon to make the most of your trip!

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The Best Things to Do in Oregon in 5 Days

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Table of Contents

  • Day 1:
    • Arrive in Portland
    • Drive to Mount Hood
    • Check into your Airbnb
    • Dinner at Chicali Cantina
  • Day 2:
    • Breakfast at Dragonfly Cafe
    • Drive the “Waterfall Highway” in the Columbia River Gorge
    • Discover Farm-fresh Food on the Hood River Fruit Loop Drive
    • Enjoy the views at Trillium Lake
    • Dinner at Mount Hood Village
  • Day 3:
    • Explore Portland
    • Drive to Oceanside
    • Dinner at Roseanna’s Cafe
  • Day 4:
    • Morning Walk on the Beach
    • Ride E-bikes on the Beach in Pacific City
    • Dinner and S’mores on the Beach
  • Day 5:
    • Visit Tillamook Creamery
    • Take a Ride on the Oregon Coast Scenic Railroad
    • Drive to Cannon Beach

Day 1:

Arrive in Portland

Today will be a travel day, whether you are flying or driving into Oregon.

If you are flying, you’ll want to fly into Portland and pick up a rental car. I would recommend checking RentCars or Expedia for the best rates on rental cars.

Drive to Mount Hood

After getting a rental car, you’ll want to drive about 50 minutes east of the city and enjoy the beauty of Mount Hood, one of Oregon’s most scenic destinations.

Check into your Airbnb

I would highly recommend booking a cozy cabin near Mount Hood for a few nights.

We booked this cabin in Brightwood on Airbnb and especially loved soaking in the hot tub overlooking the river.

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It was a great location close to restaurants and shops, but felt private and secluded.

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Dinner at Chicali Cantina

After dropping your luggage off, head to dinner at Chicali Cantina in Mount Hood Village.

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Enjoy fresh homemade guacamole and salsa and a big fat burrito on their outdoor patio.

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End the evening soaking under the stars in the hot tub while listening to the babbling sounds of the creek below.

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It’s the best way to end a long travel day!

Day 2:

Breakfast at Dragonfly Cafe

Start your day with a hearty home-cooked meal at the nearby Dragonfly Cafe.

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Our favorites are the giant cinnamon roll, the biscuits & gravy, the steel-cut oatmeal, the french toast, and the most delicious hashbrowns.

Drive the “Waterfall Highway” in the Columbia River Gorge

The Columbia River Highway is the first scenic highway in the US to be designated as a National Historic Landmark.

It crosses through some of the most scenic landscapes in Oregon and is home to countless waterfalls.

Latourell Falls is the first waterfall you’ll come to and I would recommend taking the short 0.2-mile trail to the base of the falls.

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There is a longer 2.1-mile loop trail that goes up above the waterfall if you have time.

You’ll also want to stop at Bridal Veil Falls a little further up the road. Here you will find a 0.6-mile out-and-back trail leading to the base of a two-tier 120-foot waterfall.

There is also the option to take a 0.4-mile loop trail to a scenic overlook of the Columbia River Gorge.

You definitely won’t want to miss Multnomah Falls, visiting it is one of the best things to do in Oregon.

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This 620-foot-tall waterfall is the tallest in Oregon and is the crowning jewel of the Columbia River Gorge.

Just keep in mind that timed reservations are required from the end of May until the beginning of September.

There are plenty of other waterfalls to visit in the gorge, but those are a few that you won’t want to miss!

Discover Farm-fresh Food on the Hood River Fruit Loop Drive

The “Fruit Loop” is a 35-mile scenic drive in the Hood River Valley that can be accessed from the Columbia River Highway.

It will take you past farm-to-table restaurants, roadside fruit stands, wineries, orchards, and flower fields.

I would recommend stopping for lunch at The Gorge White House.

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Order their flatbread pizza or burgers that are made with ingredients grown right at the farm.

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You can also pick fresh produce or flowers in their U-pick orchards and fields.

The Hood River Lavender Farm is a great place to stop for lavender-infused products and to take photos in the summer when the lavender is in full bloom.

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Packer Orchards & Bakery is our favorite spot to pick up fresh fruit and homemade goodies like pies, cinnamon rolls, jams, cookies, and so much more!

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Enjoy the views at Trillium Lake

As you make your way back to the Airbnb, you’ll pass by Trillium Lake.

Take the short detour through Trillium Lake Campground until you reach the Trillium Lake Dam parking lot.

Here, you will be able to see Mount Hood perfectly reflected in the water.

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The best time to visit is early in the morning or later in the evening to capture the mirrored reflection .

In the summer, paddle board rentals are available on the beach near the dam.

Dinner at Mount Hood Village

There are several different dining options in Mount Hood.

I would recommend Koya Kitchen for Asian-fusion dishes served in a cozy ambiance, Brightwood Tavern for hearty burgers and pizza, Skyway Bar & Grill for smoked meats and barbecue, or Al Forno Ferruza for authentic Italian dishes.

For more details and recommendations in the area, see our guide 10 Things to do in Mount Hood, Oregon.

Day 3:

Explore Portland

For this 5-day Oregon itinerary, I would highly recommend spending a few days in the mountains and a few days on the coast to take advantage of all that Oregon has to offer.

While driving from Mount Hood to the coast, stop and spend a few hours in Portland exploring the city.

Mississippi Avenue is a great walkable neighborhood with trendy shops and restaurants.

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Stop for brunch at Gravy and order their buttermilk biscuits that are swimming in a savory sausage gravy.

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The creme brulee oatmeal is almost too pretty to eat, but tastes as good as it looks!

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Powell’s Books is also worth a stop.

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It is the world’s largest new & used bookstore, there’s no place quite like it!

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23rd Avenue has some fun boutique shops, and be sure to stop at Salt & Straw for a scoop of their delicious hand-crafted ice cream.

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Drive to Oceanside

There are plenty of great places to stay along Oregon’s Coast, but we love Oceanside. It is a bit of a hidden gem away from the crowds.

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We stayed in this beach cottage overlooking the ocean and loved it.

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A few other options for accommodations includeThe Oceanside Inn, theCoastal Comfort, and theBlue Moonvacation home.

Dinner at Roseanna’s Cafe

Oceanside is a small community with several restaurants and cafes within walking distance from the beach.

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Roseanna’s Cafe is a great option for fresh seafood and spectacular ocean views at sunset.

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Day 4:

Morning Walk on the Beach

Mornings on the coast of Oregon are often moody with heavy mist-shrouded skies and a thick fog rolling off the ocean.

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I would recommend fully embracing the quintessential Oregon weather by taking a morning walk on the beach.

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The Oceanside Beach Trail is a 0.86-mile out-and-back trail that leads along the scenic coast. This is a great beach for shelling and rockhounding, so keep your eyes peeled for sand dollars and agates.

Ride E-bikes on the Beach in Pacific City

Pacific City is one of the few places in Oregon where you can legally drive a motorized vehicle on the beach.

The miles of scenic coastline also make it one of the best places to ride an e-bike right on the beach.

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Fat tire e-bike rentals are located in town and there are several different rides that you can do.

We loved the 10-mile roundtrip ride along Bob Straud Beach to the end of the spit, it was one of our favorite things to do in Oregon!

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McPhillips Beach is also a great place to ride and take in the stunning formations at Cape Kiwanda.

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There are also several bike paths through town where you can stop and grab a bite to eat at Grateful Bread Bakery, or a sweet treat at Pacific Coast Candy Shop.

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Dinner and S’mores on the Beach

On the way back to your vacation rental, stop at a grocery store and pick up some ingredients for dinner and s’mores.

We stopped at Safeway in Tillamook and got ingredients for soup, salad, and garlic bread. After going and doing so much, it’s nice having a relaxing evening staying in.

You’ll also want to pick up a fire starter log and ingredients for s’mores.

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Oceanside is one of the few beaches in Oregon that allows beach fires and you’ll find several designated fire pits in the sand.

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As long as there are no fire restrictions in place, it’s such a memorable experience to roast s’mores at sunset with the ocean waves crashing in the background.

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It truly was one of our favorite things to do in Oregon.

Day 5:

Visit Tillamook Creamery

Tillamook Cheese has a reputation for being some of the best cheese on the market!

The Tillamook Creamery is located about 20 minutes from Oceanside in the small farming community of Tillamook, Oregon.

Visitors can stop in and take a free self-guided tour to witness first-hand how the cheese is made.

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You can also sample fresh cheese, pick up some “cheesy” souvenirs, and try deep-fried cheese curds and housemade ice cream from the cafe.

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Take a Ride on the Oregon Coast Scenic Railroad

The Oregon Coast Scenic Railroad hosts a variety of scenic coastal train rides throughout the year.

In the fall, they offer leaf-peeping train rides, and there are themed holiday train rides in the winter.

During the warmer months, the scenic 30-minute train ride from Garibaldi to Rockaway Beach is a popular option.

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Once you reach Rockaway Beach, you can get out and explore the cute oceanfront town before heading back to Garibaldi. Tickets are reasonably priced and it’s a fun afternoon activity!

Drive to Cannon Beach

Cannon Beach is one of the most iconic spots in all of Oregon. It is the backdrop for many blockbuster films, including the 1980s classic, The Goonies.

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Cannon Beach has also earned the title of “One of the World’s Most Beautiful Places”, according to National Geographic.

It is worth making the one-hour drive from Oceanside to Cannon Beach to see the famous 235-foot Haystack Rock that Cannon Beach is famous for.

While you are there, check out the tidepools at the base of Haystack Rock, enjoy a meal with a view at Wayfarer Restaurant, and pick up some souvenirs along North Hemlock Street.

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For more details and recommendations in the area, see our guide 7 Things to Do in Oceanside, Oregon.

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After you’re done visiting Cannon Beach, it’s time to head back and pack up for your trip home.

It’s always sad to see a trip come to an end, but hopefully this itinerary will help you discover the best things to do in Oregon so that you can make the most of your time there!

If you’re looking for more girls’ trip inspiration, see our guide 11 Best Girls’ Trip Destinations in the US!

*Click the button to download and print this guide to take with you on your trip!

5 Day Oregon Itinerary

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