Oregon
5
Day Itinerary •
USA
Five days in Oregon lets you explore the full extraordinary breadth of the Pacific Northwest state, from the vibrant food cart culture and Powell's Books of Portland to the extraordinary blue of Crater Lake, the deepest lake in America, the magnificent Columbia River Gorge waterfall corridor and the wild Oregon Coast. This route covers the complete Oregon experience. The extraordinary Multnomah Falls and Crown Point of the Historic Highway, the most extraordinary blue water in North America at Crater Lake National Park, the extraordinary Haystack Rock of Cannon Beach, the finest pinot noir wine country of the Willamette Valley and the wild southern Oregon Coast.
Best Time To Visit
July to September for Crater Lake, June to October for coast
Getting There
Fly into Portland International (PDX)
Getting Around
Rental car essential for Crater Lake, coast and wine country
Budget Per Day
Approx $120 to $190 per person per day
Difficulity
Easy to moderate, some volcanic and coastal hiking
DAY 1
PORTLAND
MORNING
POWELL'S BOOKS AND THE PEARL DISTRICT
Powell's City of Books is the most extraordinary independent bookshop in America, its city block of 68,000 square feet housing over one million new and used books across nine color-coded rooms. The Pearl District surrounding Powell's is the finest arts and gallery neighborhood in Portland, its extraordinary converted warehouse galleries and craft coffee shops giving the most vibrant creative quarter in the Pacific Northwest. The Portland Saturday Market is extraordinary. Free. Drive: 15 min walk
MIDDAY
PORTLAND FOOD CARTS AND THE CENTRAL EASTSIDE
Portland's food cart scene is the most extraordinary in America, its 500-plus vendors of extraordinary international cuisine concentrated in pod clusters across the city. The Central Eastside industrial district with its extraordinary distilleries, cideries and the Portland Mercado is the finest emerging food neighborhood in the city. The extraordinary Lan Su Chinese Garden in Old Town is the finest classical Chinese garden in North America. Garden entry approx $14. Drive: 20 min walk
AFTERNOON
FOREST PARK AND THE PITTOCK MANSION
Forest Park is the most extraordinary urban forest in America, its 5,200 acres of temperate rainforest with 80 miles of trail entirely within Portland. Pittock Mansion above the park is the most extraordinary historic house in the city, its 1914 French Renaissance revival given the finest panoramic view over Portland and Mount Hood. The Wildwood Trail through old-growth Douglas fir is the finest urban trail in America. Park free, mansion entry approx $12.
💎 HIDDEN GEM
The extraordinary Lan Su Chinese Garden in Portland is the finest classical Chinese garden in North America, its Ming Dynasty-style courtyards built by craftspeople from Suzhou. The teahouse serves the finest traditional tea ceremony in Oregon. Entry approx $14. The most extraordinary hidden cultural gem in Portland, unknown to most visitors.
🍽 WHERE TO EAT
Breakfast: Tasty n Daughters, Portland The finest breakfast in Portland. Extraordinary daily changing menu and local eggs. | Lunch: Portland food cart pod, SW 10th The most extraordinary food cart experience in America. Twenty nationalities in one block. | Dinner: Le Pigeon, Portland The finest restaurant in Portland. Extraordinary French-influenced Pacific Northwest cuisine. Book ahead.
DAY 2
COLUMBIA RIVER GORGE
MORNING
MULTNOMAH FALLS AND THE HISTORIC HIGHWAY WATERFALL CORRIDOR
Multnomah Falls is the most extraordinary waterfall in Oregon, its extraordinary 620-foot two-tiered cascade visible from the 1925 Multnomah Falls Lodge. The Historic Columbia River Highway waterfall corridor past Latourell Falls, Bridal Veil, Wahkeena and Crown Point Vista House is the most extraordinary concentration of waterfalls in North America. Crown Point at 733 feet gives the finest panoramic view of the Columbia River Gorge. Entry free, parking timed. Drive: 30 min drive
MIDDAY
HOOD RIVER AND THE COLUMBIA GORGE WINERIES
Hood River is the most extraordinary small town in the Columbia River Gorge, its extraordinary position between the windsurfing capital of America and the orchards of the Hood River Valley. The Columbia Gorge wine region produces the finest Gewurztraminer and Pinot Gris in Oregon. The Hood River Valley fruit loop driving through orchards and farm stands in spring blossom is extraordinary. The view of Mount Hood from downtown Hood River is extraordinary. Free. Drive: 30 min drive
AFTERNOON
ONEONTA GORGE AND THE GORGE HIDDEN GEMS
The Oneonta Gorge is the finest hidden slot canyon in Oregon, its extraordinary narrow basalt passage requiring a wade through a log jam pool to reach the extraordinary 100-foot Oneonta Falls. The Angel's Rest trail above the gorge gives the finest elevated view of the entire Columbia River Gorge in a 4.6-mile round trip to a 1,600-foot basalt outcrop. Both are extraordinary experiences entirely unlike the main Multnomah Falls corridor. Entry free.
💎 HIDDEN GEM
The extraordinary Latourell Falls near the western end of the Historic Highway is the finest easily accessible waterfall in the Columbia Gorge, its extraordinary 249-foot single-tier plunge past a columnar basalt cliff face with a 2-mile loop trail giving the most extraordinary close-range waterfall experience in Oregon. Entry free. Far less visited than Multnomah Falls.
🍽 WHERE TO EAT
Breakfast: Multnomah Falls Lodge Restaurant Extraordinary breakfast at the base of the finest waterfall in Oregon. Local eggs and strong coffee. | Lunch: Solstice Wood Fire Cafe, Hood River Outstanding wood-fired pizza and Oregon craft beer in the finest casual restaurant in Hood River. | Dinner: Celilo Restaurant, Hood River The finest restaurant in the Columbia Gorge. Extraordinary local Pacific Northwest cuisine and Oregon wine.
DAY 3
CRATER LAKE NATIONAL PARK
MORNING
CRATER LAKE NATIONAL PARK, THE MOST EXTRAORDINARY BLUE WATER IN AMERICA
Crater Lake is the most extraordinary lake in America, its extraordinary 1,943-foot depth making it the deepest lake in the United States and its extraordinary clarity giving the most intense blue color of any body of water in North America. The caldera formed 7,700 years ago when Mount Mazama erupted and collapsed in the most catastrophic volcanic event in the history of the Pacific Northwest. The Rim Village view at sunrise is the most extraordinary in Oregon. Entry $35. Drive: 30 min drive
MIDDAY
RIM DRIVE AND WIZARD ISLAND
The 33-mile Rim Drive circling Crater Lake gives the most extraordinary succession of lake viewpoints in America, its extraordinary overlooks at Cloudcap, Phantom Ship Island, Pumice Castle and the Watchman giving different perspectives of the extraordinary blue water at every turn. The Wizard Island boat tour landing on the cinder cone inside the caldera is the most extraordinary experience in Crater Lake National Park. Book at recreation.gov months ahead. Approx $55. Drive: 2 hr drive
AFTERNOON
DIAMOND LAKE AND THE UMPQUA NATIONAL FOREST
Diamond Lake adjacent to Crater Lake is the most extraordinary hidden lake in southern Oregon, its extraordinary mountain lake at 5,183 feet reflecting Mount Thielsen, the Lightning Rod of the Cascades, in conditions of extraordinary clarity. The Umpqua National Forest surrounding Diamond Lake contains the finest concentration of waterfalls in Oregon outside the Columbia Gorge, including the extraordinary Watson Falls at 272 feet. Entry free.
💎 HIDDEN GEM
The extraordinary Cleetwood Cove trail is the only trail to the water's edge at Crater Lake, its extraordinary 2.2-mile round trip descending 700 feet to the lake shore where the water is extraordinary in its clarity and cold. Swimming is permitted. The boat to Wizard Island departs here. The most extraordinary hidden experience in Crater Lake National Park. Free with park entry.
🍽 WHERE TO EAT
Breakfast: Crater Lake Lodge dining room The most extraordinary breakfast setting in Oregon. Coffee overlooking the blue caldera at 7,100 feet. | Lunch: Rim Village Cafe Outstanding casual lunch at the caldera rim. Local Oregon ingredients and craft beer at 7,100 feet. | Dinner: Crater Lake Lodge dining room The finest dinner in southern Oregon. Local Pacific Northwest cuisine with extraordinary lake views.
DAY 4
OREGON COAST
MORNING
CANNON BEACH AND HAYSTACK ROCK
Cannon Beach is the most extraordinary beach town in Oregon, its extraordinary 235-foot Haystack Rock rising from the surf in one of the most photographed coastal scenes in America. At low tide the tidal pools teem with purple sea urchins, starfish and nesting tufted puffins. The Ecola State Park headland trail above the beach gives the most extraordinary elevated view of Haystack Rock and the Oregon coastline to the north. Rock area free, park entry $5. Drive: 30 min drive
MIDDAY
SAMUEL H. BOARDMAN STATE SCENIC CORRIDOR
The Samuel H. Boardman State Scenic Corridor near Brookings in southern Oregon is the most extraordinary stretch of the entire Oregon Coast, its extraordinary 12-mile corridor of sea arches, natural bridges, offshore rocks and old-growth Sitka spruce headlands entirely unknown to the majority of visitors who focus on Cannon Beach and the north coast. Natural Bridges Cove and Arch Rock are the most extraordinary viewpoints. Entry free. Drive: 1.5 hr drive
AFTERNOON
OSWALD WEST STATE PARK AND SHORT SANDS BEACH
Oswald West State Park is the most extraordinary state park on the Oregon Coast, its extraordinary Short Sands Beach in a forested cove accessible only by a half-mile trail through old-growth Sitka spruce. The Cape Falcon headland trail gives the finest view of the Oregon Coast in any state park. The surf at Short Sands is the finest bodyboarding beach in Oregon. The old-growth Sitka spruce forest surrounding the park is extraordinary. Entry free.
💎 HIDDEN GEM
The extraordinary Cape Lookout State Park south of Tillamook gives the finest hidden headland hike on the northern Oregon Coast, its extraordinary 5-mile round trip trail through old-growth Sitka spruce to a narrow cape tip 400 feet above the Pacific giving views of gray whale migration in spring and fall. Entry free. Almost entirely unknown to visitors in Cannon Beach.
🍽 WHERE TO EAT
Breakfast: Sleepy Monk Coffee, Cannon Beach The finest organic coffee in Oregon. Extraordinary pour-overs and pastries before Haystack Rock. | Lunch: Picnic at Short Sands Beach Pack lunch from Cannon Beach. The extraordinary picnic tables in the old-growth forest above the surf. | Dinner: Newman's at 988, Cannon Beach The finest restaurant in Cannon Beach. Extraordinary Pacific Northwest cuisine and Oregon Pinot Noir.
DAY 5
WILLAMETTE VALLEY
MORNING
WILLAMETTE VALLEY PINOT NOIR, THE FINEST WINE COUNTRY IN AMERICA
The Willamette Valley is the most extraordinary Pinot Noir wine region in America, its extraordinary combination of marine influence, volcanic Jory soil and cool growing season producing Pinot Noir that rivals Burgundy in concentration and finesse. The Dundee Hills and Chehalem Mountains sub-AVAs contain the finest producers. Domaine Drouhin, Sokol Blosser, Ponzi and Adelsheim are among the most extraordinary. Tasting room fees approx $15 to $30. Drive: 30 min drive
MIDDAY
MCMINNVILLE AND THE DOWNTOWN WINE SCENE
McMinnville is the most extraordinary wine town in Oregon, its extraordinary Third Street of Victorian brick buildings housing the finest concentration of independent wine bars, farm-to-table restaurants and artisan food shops in the Pacific Northwest. The Evergreen Aviation and Space Museum on the edge of town contains Howard Hughes's extraordinary Spruce Goose, the largest flying boat ever built, and is the most extraordinary aviation museum in Oregon. Museum entry approx $27. Drive: 30 min drive
AFTERNOON
NEWBERG AND THE CHEHALEM MOUNTAINS WINE TRAIL
The Chehalem Mountains above Newberg contain some of the finest single-vineyard Pinot Noir in Oregon, their extraordinary combination of Jory volcanic and Laurelwood sedimentary soils giving a complexity of flavor that the best Burgundy producers recognize as genuinely world-class. The Rex Hill winery with its extraordinary cave cellar and Adelsheim Vineyard with its hilltop views are the finest tasting experiences near Newberg. Tasting approx $20.
💎 HIDDEN GEM
The extraordinary Stoller Family Estate above Dayton is the finest biodynamic winery experience in the Willamette Valley, its extraordinary hillside tasting room with panoramic views over the Chehalem Mountains giving the finest elevated perspective of wine country in Oregon. Tasting approx $25. Almost entirely booked by locals and wine professionals.
🍽 WHERE TO EAT
Breakfast: Red Hills Market, Dundee The finest farm-to-table breakfast in the Willamette Valley. Local eggs, Oregon charcuterie and strong coffee. | Lunch: Nick's Italian Cafe, McMinnville The most legendary restaurant in wine country since 1977. Extraordinary local pasta and Oregon Pinot Noir. | Dinner: The Joel Palmer House, Dayton The finest mushroom-focused restaurant in Oregon. Extraordinary local ingredients in the wine country heartland.
Where To Stay
Portland, Night 1 Ace Hotel Portland or Hotel Lucia downtown. Approx $140 to $250 per night. Crater Lake or Ashland, Nights 2 to 3 Crater Lake Lodge inside the park or Ashland Springs Hotel. Approx $150 to $280. Cannon Beach or McMinnville, Nights 4 to 5 Stephanie Inn Cannon Beach or Hotel McMenamin. Approx $150 to $300 per night.
Top Tips
1. Crater Lake Lodge dining room at sunset with the lake turning gold is the most extraordinary dinner setting in Oregon.
2. Multnomah Falls parking fills by 9am. Arrive at 7am or take the Historic Highway shuttle from Corbett.
3. Wizard Island boat tour in Crater Lake must be booked at recreation.gov months ahead. Extraordinary.
4. Willamette Valley Pinot Noir is the finest in America. Sokol Blosser and Domaine Drouhin are extraordinary.
5. Samuel H. Boardman corridor near Brookings is the most extraordinary stretch of the Oregon Coast. Almost no visitors.
6. Oneonta Gorge near Multnomah Falls requires wading a pool but gives the most extraordinary hidden falls in Oregon.
Total Budget
$120 to $190/day