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AT A GLANCE
Oregon’s wild beauty is calling! This 5-day adventure takes you from Portland to the rugged Oregon Coast and deep into the lush forests of the Pacific Northwest. We’ll chase waterfalls in the Columbia River Gorge, surf the waves at Cannon Beach, and explore the charming coastal towns of Manzanita and Tillamook. From hiking scenic trails and spotting sea lions to cozy evenings by the coast and local brews at Pelican or Public House Brewery, this trip blends outdoor adventure with Oregon’s laid-back charm. With nights spent between Portland, Cannon Beach, and the coast, you’ll experience the best of what makes Oregon so unforgettable.
ITINERARY
What To Expect
After landing in Portland, Oregon on March 26, we’ll hop into the Outsiders vans and begin our journey toward the Oregon Coast, where our adventure kicks off. We’ll settle into our accommodations in Cannon Beach for the next two nights before diving into the week’s activities. Please plan to arrive in Portland before noon on XXX to ensure a smooth start to the trip.
Day 1 - May 21
Welcome to Oregon! After arriving in Portland, we’ll meet up at a designated meet up location and hit the road, heading northwest for a scenic two-hour drive to the charming coastal town of Astoria—where the Columbia River meets the Pacific Ocean.
Once we arrive, we’ll spend the afternoon exploring Astoria’s rich maritime history and quirky local attractions. We’ll stop by the Columbia River Maritime Museum to learn about the region’s seafaring past, visit the Oregon Film Museum—set inside the old jail featured in The Goonies—and, of course, swing by the iconic Goonies House for a photo op.
As evening sets in, we’ll stroll along the Astoria Riverwalk, watching ships glide by on the Columbia, or climb the Astoria Column for panoramic views of the town, river, and ocean beyond. We’ll wrap up the day with dinner and craft beer at Fort George Brewery or Buoy Beer Company, both local favorites serving up fresh coastal fare and laid-back vibes.
We’ll spend the night in Astoria, resting up before continuing our Oregon coast adventure tomorrow.
Day 2 - May 22
After breakfast, we’ll take a scenic 40-minute drive south to Ecola State Park, a coastal gem known for its mossy forests, dramatic cliffs, and sweeping ocean views. We’ll hike the Indian Beach Trail, which winds from Ecola Point to Indian Beach, offering lush forest paths, panoramic seaside vistas, and plenty of photo-worthy stops along the way.
In the afternoon, we’ll arrive in Cannon Beach, one of Oregon’s most picturesque coastal towns. Enjoy some free time exploring the charming downtown area—browse boutique shops, art galleries, and cozy cafés.
As the day winds down, we’ll gather on the shore to watch a stunning sunset at Haystack Rock, the iconic monolith rising from the surf. Dinner follows at Ecola Seafoods or Public Coast Brewing Co., where you can enjoy casual, local coastal fare.
Overnight in Cannon Beach.
Day 3 - May 23
We’ll start the morning at Cleanline Surf Shop in Cannon Beach to pick up boards and wetsuits for a fun day on the water. Depending on surf conditions, we’ll ride the waves at Short Sand Beach in Oswald West State Park or Indian Beach—both surrounded by dramatic cliffs and lush coastal forest. Whether you’re new to surfing or an experienced wave rider, it’s a perfect way to immerse yourself in Oregon’s rugged coastline.
In the afternoon, you’ll have options to continue exploring or relax. Visit the nearby Hug Point caves and waterfall, a hidden coastal treasure, or spend some downtime back in town strolling the beach, grabbing a coffee, or browsing local shops.
We’ll wrap up the day with dinner and craft beer at Pelican Brewing, the ideal post-surf hangout to celebrate another incredible day along the Oregon Coast.
Overnight in Cannon Beach.
Day 4 - May 24
DAY 4 – MARCH 30
We’ll ease into the morning with coffee and fresh-baked pastries at Sleepy Monk Coffee Roasters, a beloved Cannon Beach staple known for its cozy vibe and expertly roasted blends. Before heading inland, we’ll make an optional stop at the Neahkahnie Mountain viewpoint, where sweeping coastal vistas stretch as far as the eye can see—a perfect final glimpse of Oregon’s rugged shoreline.
From there, we’ll make the scenic drive back to Portland (about 1.5 to 2 hours), watching the coastline give way to forested hills and open valleys along the way.
Once we arrive, we’ll settle into our hotel and spend the evening exploring Portland’s Pearl District, one of the city’s most vibrant neighborhoods. Browse the shelves at Powell’s City of Books, grab a local brew at one of the area’s many craft breweries, and enjoy dinner at a nearby restaurant featuring Portland’s creative food scene.
We’ll overnight in Portland, ready to cap off our Oregon adventure with one more day of exploration.
Day 5 - May 25
On our final day, we’ll head east for a short 45-minute drive to the breathtaking Columbia River Gorge, one of Oregon’s most iconic natural wonders. We’ll lace up our hiking shoes and explore some of the area’s stunning trails—choose from Multnomah Falls, Oregon’s tallest waterfall, the serene Latourell Falls, or the panoramic summit hike to Angel’s Rest.
Along the way, we’ll stop at the Vista House, perched high above the gorge, for iconic views of the winding river and lush valley below—perfect for one last photo op of Oregon’s wild beauty.
In the afternoon, we’ll return to Portland for a casual lunch at one of the city’s famous food truck pods or take a stroll through the vibrant Alberta Arts District, exploring local galleries, shops, and murals.
If time allows before your departure, enjoy a leisurely walk along the Waterfront Park Esplanade, taking in the city skyline and riverfront one last time. Then, we’ll make our way to the airport for departure, wrapping up an unforgettable five-day Oregon adventure.
AVAILABLE ACTIVITIES
HERE’S THE BREAKDOWN OF
WHAT’S INCLUDED
Transportation throughout the week between destinations along the Oregon Coast and Portland (does not include airport transfers)
1 Night in Astoria
2 Nights in Cannon Beach
1 Night in Portland
Guided hikes at Ecola State Park, Indian Beach Trail, Columbia River Gorge (choose from Multnomah Falls, Latourell Falls, or Angel’s Rest)
Surfboard and wetsuit rentals at Cleanline Surf Shop
Visit to Hug Point caves and waterfall
Scenic drives along the Oregon Coast and Columbia River Gorge
Sightseeing and exploration stops: Astoria Column, Columbia River Maritime Museum, Oregon Film Museum, Goonies House, Vista House
Time to explore charming coastal towns, downtown Cannon Beach, and Portland neighborhoods (Pearl District, Alberta Arts District)
Please Note: Airfare to and from Portland is not included in this package.
