Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

5-Day Road Trip Adventure in Portland, Oregon

Viewed by 92 travelers

Day 1: Portland Exploration

Portland, Oregon

8:00 AM

Breakfast at Mother's Bistro

Savor a hearty breakfast at Mother's Bistro, known for its comforting, homemade breakfasts with a twist.
Located in downtown, easy access from any Portland hotel.
USD20, 1 hour

9:30 AM

Visit the Portland Japanese Garden

Stroll through the beautiful, tranquil Portland Japanese Garden, one of the most authentic Japanese gardens outside of Japan itself.
Short drive or 15-minute walk from Mother's Bistro.
USD19, 2 hours

12:00 PM

Lunch at Pine Street Market

Enjoy a diverse array of food options from local vendors at this trendy food hall.
Just a 10-minute drive from the garden.
USD15, 1 hour

1:30 PM

Explore Powell's City of Books

Wander around the largest independent bookstore in the world, where you can lose track of time among the countless shelves of books.
A quick 5-10 minute drive from Pine Street Market.
Free, 1.5 hours

3:00 PM

Walk at Waterfront Park

Take a leisurely stroll along the river at Waterfront Park, soaking in views of the Portland skyline and the Willamette River.
Just a 5-minute drive from Powell's.
Free, 1 hour

6:00 PM

Dinner at The Observatory

Conclude the day with dinner at The Observatory, known for its seasonal dishes and fantastic views of the city.
A 15-minute drive from Waterfront Park.
USD35, 1.5 hours
Find Hotels in Portland

Day 2: Columbia River Gorge

Columbia River Gorge, Oregon

8:00 AM

Breakfast at Blue Star Donuts

Start your day with a gourmet donut from Blue Star, known for their unique and delicious flavors.
Short drive from your accommodation in Portland.
USD10, 30 minutes

9:00 AM

Drive to Columbia River Gorge

Take the scenic 30-minute drive to Columbia River Gorge, a must-see in Oregon’s landscape.
Follow I-84 E for beautiful river views.
Free until destination, 30 minutes

9:30 AM

Hike to Multnomah Falls

Hike the short but stunning trail to Multnomah Falls, the tallest waterfall in Oregon.
Short walk from the parking area.
Free, 2 hours

12:00 PM

Lunch at Bonneville Hot Springs Resort

Enjoy lunch with a view at Bonneville Hot Springs, offering a selection of American cuisine.
Short drive from the falls.
USD25, 1 hour

1:30 PM

Visit Crown Point Vista House

Stop at Crown Point Vista House for panoramic views of the gorge and great photo opportunities.
About a 20-minute drive from the resort.
Free, 1 hour

3:00 PM

Explore Rowena Crest Viewpoint

Take in breathtaking views at Rowena Crest to see the Columbia River winding through the gorge.
A short 30-minute drive along the scenic highway.
Free, 1.5 hours

6:00 PM

Dinner at Thunder Island Brewing

Enjoy a casual meal and craft beer with views of the Columbia River.
20-minute drive back to Hood River.
USD30, 1.5 hours
Find Hotels in Columbia River Gorge

Day 3: Mount Hood Adventure

Mount Hood, Oregon

8:00 AM

Breakfast at Egg River Cafe

Fuel up with a hearty breakfast at Egg River Cafe, celebrated for its breakfast fare.
Drive 1 hour from Hood River towards Mount Hood.
USD20, 1 hour

9:30 AM

Visit Timberline Lodge

Explore the iconic Timberline Lodge, a historic landmark that offers stunning views and fascinating history.
30-minute drive from Egg River Cafe.
Free, 1.5 hours

11:00 AM

Scenic Drive on Mt. Hood Scenic Byway

Take a leisurely drive along the Mt. Hood Scenic Byway, showcasing Oregon’s exquisite natural beauty.
Drive straight through the scenic byway.
Free, 2 hours

1:00 PM

Lunch at The Rendezvous Grill

Stop for lunch at The Rendezvous Grill, known for its local flavors and cozy atmosphere.
Located on the scenic byway.
USD25, 1 hour

2:30 PM

Hiking in Trillium Lake

Hike at Trillium Lake, where you can enjoy picturesque views and possibly spot some wildlife.
A quick 20-minute drive from the restaurant.
Free, 2 hours

5:00 PM

Dinner at Mt. Hood Brewing Co.

Relax and unwind with dinner at Mt. Hood Brewing Co., offering a great selection of beers and hearty dishes.
20-minute drive from Trillium Lake.
USD30, 1.5 hours
Find Hotels in Mount Hood

Day 4: Cannon Beach Excursion

Cannon Beach, Oregon

8:00 AM

Breakfast at The Pancake House

Start your day with fluffy pancakes at The Pancake House, beloved by locals and tourists alike.
A 1-hour drive from Mount Hood.
USD15, 1 hour

9:30 AM

Drive to Cannon Beach

Head out on a scenic drive to Cannon Beach, known for its iconic Haystack Rock.
Follow the coastal highway for stunning views.
Free, 1.5 hours

11:00 AM

Beach Day at Cannon Beach

Spend time exploring Cannon Beach, taking photos of Haystack Rock, and soaking in the sun.
Parking available near the beach.
Free, 2 hours

1:00 PM

Lunch at The Wayfarer Restaurant

Dine at The Wayfarer, offering fresh seafood and stunning waterfront views.
Short walk from Canon beach.
USD30, 1.5 hours

2:30 PM

Visit Ecola State Park

Explore the stunning coastal viewpoints and trails at Ecola State Park.
5-minute drive from the restaurant.
USD5, 2 hours

6:00 PM

Dinner at Seaside Brewing Company

Enjoy a relaxed dinner at Seaside Brewing Company, known for its craft beer and pub-style meals.
A quick 15-minute drive from the park.
USD25, 1.5 hours
Find Hotels in Cannon Beach

Day 5: Portland Wrap-Up

Portland, Oregon

8:00 AM

Breakfast at Tasty n Alder

Start your final day in Portland with a breakfast of seasonal dishes at Tasty n Alder, worth the wait.
A 2-hour drive back to Portland.
USD25, 1.5 hours

10:00 AM

Visit Oregon Museum of Science and Industry (OMSI)

Spend some time at OMSI, enjoying hands-on exhibits and an IMAX theater.
Located 10-minute drive from the restaurant.
USD16, 2 hours

12:00 PM

Lunch at Deschutes Brewery

Enjoy lunch paired with craft beer at Deschutes Brewery's Portland location.
Just a short drive from OMSI.
USD25, 1 hour

1:30 PM

Shopping at the Pearl District

Explore the Pearl District, known for its trendy shops and galleries.
A quick drive from the brewery.
Free, 2 hours

3:30 PM

Visit Portland Art Museum

Finish your trip with a visit to the Portland Art Museum, showcasing an impressive collection of art.
A 10-minute drive from Pearl District.
USD20, 1.5 hours

6:00 PM

Farewell Dinner at Andina Restaurant

Enjoy a memorable farewell dinner at Andina, offering vibrant Peruvian cuisine and a lively atmosphere.
10-minute drive from the art museum.
USD35, 2 hours
Find Hotels in Portland
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version

More About portland oregon

5-Day Portland, Oregon — October Trip
Packing List
5-Day Portland, Oregon — October Trip
Packing List
Itinerary created by AI-assisted, human-reviewed

Plan Your portland oregon Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go