A journey around Oregon provides a bold study in contrasts. In this land of makers, you’ll encounter countless purveyors of craft beer, carefully sourced and roasted coffees, exquisitely prepared farm-to-table foods, and legions of artisans who handcraft everything from ukuleles to bicycles. Good food needs good wine and Oregon provides! There are nearly 700 wineries in the state of Oregon, the most popular grapes grown being pinot noir and pinot gris.
You’ll also pass through an untamed landscape that showcases Oregon’s wild side and delights photographers, hikers and nature lovers. The state’s scenic highways pass by rushing rivers abundant with salmon and steelhead, craggy mountain peaks capped year-round with snow, eerie-looking lava beds littered with bizarre geological formations, and rugged stretches of coastline dominated by massive headlands and fragrant pine forests. Here’s a taste of it all.
This itinerary is flexible and can be tailor-made to suit you; if you want to add extra days in one area, extend the holiday or maybe change the direction of travel. Talk to one of our experts about how to make this holiday the perfect one for you.
We used Frontier Travel to book our honeymoon. We were given all the information we needed and everything ran seamlessly. We had a fantastic time, the hotels and lodges were perfect. Thank you for organising such a brilliant trip!
Itinerary (11 Nights)
Here’s a day-by-day guide to your itinerary. Feel free to ask us to add other days or ideas and excursions by contacting us directly, so we can give you the best price.
A direct flight from the UK to Portland will start your holiday off in fine...
A direct flight from the UK to Portland will start your holiday off in fine style. Renowned for its locavore-driven food scene, independent-spirited shopping and gloriously verdant parks, Portland offers enough cultural and outdoorsy diversions to keep you busy for a week, but it’s also a surprisingly easy city to get to know in a day. Enjoy brunch at lively Tasty n Alder, where the chocolate-potato doughnuts provide the perfect prelude to lemon- ricotta pancakes with huckleberry syrup.
Then walk off your decadent meal through the Pearl District, a former industrial neighborhood that’s now rife with art galleries and modish boutiques. It is also home to legendary Powell’s City of Books, the largest new and used bookstore in the world.
Continue to leafy Washington Park to tour the Portland Japanese Garden and International Rose Test Garden, or rent a two-wheeler through the handy BIKETOWN bike-share program and pedal across the Willamette River to explore the Hawthorne District’s funky vintage stores, quirky coffeehouses and offbeat bars. End your explorations by sampling the wood-aged sours and Belgian-style farmhouse beers at Breakside Brewery.
2 nights Portland
Portland to Pendleton
Less than 30 minutes’ drive east of Portland, you’ll enter the spectacular Columbia River Gorge...
Less than 30 minutes’ drive east of Portland, you’ll enter the spectacular Columbia River Gorge National Scenic Area, an 80-mile forested canyon of rugged cliffs and soaring waterfalls, much of which you can tour via the iconic Historic Columbia River Highway. Stop to snap a photo and enjoy a slice of marionberry shortcake in the 1915 lodge at Multnomah Falls; a steep but paved trail ascends to the top of this 620-foot-tall cataract. Stop for a brick-oven pizza at Double Mountain Brewery & Taproom in Hood River, a cheerful village famous for kitesurfing and wind-surfing, as well as its first-rate culinary scene. The Columbia Gorge contains more than 30 wineries, including Echo Ridge Cellars, whose tasting room occupies a retrofitted grain elevator.
In Pendleton, a friendly cowboy town acclaimed for September’s iconic Pendleton Round-Up rodeo, browse the vibrantly patterned blankets and attire at Pendleton Woolen Mills and the hand- crafted leather saddles and silver belt buckles at the Hamley & Co. Western store. Then feast on a charbroiled, hand-cut rib-eye steak from ’50s-era Virgil’s at Cimmiyotti’s.
1 night Pendleton
Pendleton to Bend
Drive south via Highway 19 and U.S. 26 through the high-desert heart of Oregon, (more...
Drive south via Highway 19 and U.S. 26 through the high-desert heart of Oregon, (more than 45% of Oregon is classed as high desert) stopping to admire the otherworldly Painted Hills section of the John Day Fossil Beds National Monument. At Smith Rock State Park, one of the nation’s top rock-climbing destinations, embark on a short trek amid the dramatic canyons and fantastic rock spires. Continue toward the majestic Cascades Range for your stop tonight, which will be in Bend where you might like to visit the High Desert Museum showcasing the local environment and its history. You might also enjoy one of one of the many craft-beers on offer in the town.
1 night Bend
Bend to Crater Lake
Just after you leave Bend, stop at the Newberry National Volcanic Monument, where you can...
Just after you leave Bend, stop at the Newberry National Volcanic Monument, where you can literally get in touch with the region’s ancient, cataclysmic geological history by walking through a lava tube and ascending Paulina Peak for panoramic high-desert views.
Your destination is Crater Lake National Park, which is anchored by the nation’s deepest lake. Hike along the rim of this 21-square-mile clear-blue lake, take a boat trip to Wizard Island, and enjoy dinner and the rustic ambience of Crater Lake Lodge, a classic timber and shingle-roof National Parks hotel built in 1915.
1 night Crater Lake National Park
Crater Lake to Ashland
Head for the ruggedly beautiful Rogue Valley and vibrant Ashland, famed for the Oregon Shakespeare...
Head for the ruggedly beautiful Rogue Valley and vibrant Ashland, famed for the Oregon Shakespeare Festival, which stages 11 classic and contemporary productions during its mid-February through October season. With its many farm-to-table eateries and the decadent Oregon Chocolate Festival in March, Ashland has become a top destination for foodies. Be sure to check out Noble Coffee Roasting, a third-wave cafe in the historic Railroad District. Also explore downtown’s many galleries and shops, as well as adjacent Lithia Park, an expanse of both groomed pathways and vertiginous trails through pine forests.
1 night Ashland
Ashland to Grants Pass
It is a short drive today – just 43 miles to allow you time to...
to Grants Pass
It is a short drive today – just 43 miles to allow you time to enjoy the Rogue Valley and its plentiful fruit orchards and grape vineyards, the endearingly old-fashioned hamlet of Jacksonville, a designated National Historic District with tasting rooms and unique retailers. Continue to Grants Pass, where you can explore the 250-foot- deep (76-m) Rogue River Canyon with a Jetboat Excursions (from 1 – 5 hours depending on your level of adventure seeking) . For a decidedly mellower adventure, book a beer- centric trip with The Paddled Pub, which partners with local Climate City Brewing Co. to provide lazy floats along a relaxing stretch of the Rogue.
1 night Grants Pass
Grants Pass to Eugene
En route north to the state’s second-largest city, Eugene, stop in Cottage Grove and rent...
En route north to the state’s second-largest city, Eugene, stop in Cottage Grove and rent a bike to ride along the 36-mile round-trip covered-bridge bike route, which traverses some of Lane County’s loveliest countryside. In Eugene, walk around the bustling campus of the University of Oregon, home to some outstanding museums and Hayward Field, one of the world’s foremost track-and-field venues. Then head to the bohemian Whitaker neighborhood to sample wine that’s crushed and bottled right in town at Territorial Vineyards & Wine Company, one of the city’s urban wineries.
1 night Eugene
Eugene to Newport
Start your day with breakfast at Provisions Market Hall, inside downtown Eugene’s handsomely restored Fifth...
Start your day with breakfast at Provisions Market Hall, inside downtown Eugene’s handsomely restored Fifth Street Market. Then drive west through Oregon’s forested Coast Range to Old Town Florence, where you can sip a single-origin coffee on the deck at Siuslaw River Coffee Roasters, which overlooks one of the many famous 1930s-era bridges set along scenic U.S. 101, the Oregon Coast Highway. Florence marks the northern end of the massive Oregon Dunes National Recreation Area, the largest expanse of coastal sand dunes in North America. At Florence’s Sand Master Park, you can learn to sandboard or book an exciting dune- buggy tour.
Follow U.S. 101 north along the Coast, stopping for quick treks at Heceta Head Lighthouse and Cape Perpetua Overlook, and visit Newport’s renowned Oregon Coast Aquarium to view playful sea otters and a giant Pacific octopus. End your day with a walk around Newport’s Historic Bayfront, where you may see (and hear) sea lions barking and dine on superb Dungeness crab cakes at Local Ocean Seafoods.
2 nights Newport
Newport to Astoria
You’ll encounter one stunning viewpoint after another as you continue up the Coast. Stop in...
You’ll encounter one stunning viewpoint after another as you continue up the Coast. Stop in Depoe Bay for a chance to view graceful gray whales on a one- hour whale-watching tour. In Cannon Beach, dip your toes in the sand with a stroll beside the imposing, 327-foot-high (100-m) Haystack Rock, and sample homemade fudge or saltwater taffy at one of the several candy shops. Then head to Indian Beach in Ecola State Park to watch surfers taming the ferocious surf or for a short hike to the Tillamook Rock Lighthouse overlook. The former salmon-canning town of Astoria occupies a magnificent setting at the confluence of the Columbia River and the Pacific Ocean where more than 2,000 ships have sunk or run aground on or near the notorious Columbia Bar.
Take in the view by climbing the 164 steps to the observation deck of the historic Astoria Column, admire the Columbia River Maritime Museum’s imaginative displays before sipping craft brews at Buoy Beer Co. The brewery sits on a pier, and you can watch sea lions through its glass floor.
1 night Astoria
Astoria to Portland
It is only a two-hour drive back to Portland airport so you could easily fly...
It is only a two-hour drive back to Portland airport so you could easily fly back today. However, if you are keen walkers, you might like to hike Saddle Mountain, a 5-mile round-trip trek with an elevation gain of 1,600 feet and spend a final night in Portland. The views of the Coast and, on clear days, Mt. Rainier and Mt. Hood are well worth the effort. Either way, you will have time to stop at Apolloni Vineyards in Forest Grove to sample outstanding Willamette Valley pinot noir.
J Smith - Travelled New York to Toronto
I have just returned from a tailor made holiday made possible by Jeannette Dembrey. This was the first time I had ever organised such a major holiday and as it was a gift for my children after my retirement it was really important to get things right. I went to quite a few agencies but Jeannette was way better than any of the people who I spoke to. She was so professional and wanted me to get the best from the money I could afford. The holiday was absolutely amazing and everything went like clockwork. Jeannette had thought of everything even the connections between places and the things we would do in each town. We stayed in 6 hotels altogether starting in New York and ending in Toronto. I am amazed at how smoothly it went. Even my son who has travelled all over the world was impressed with the way things had been organised. I cannot praise Jeannette enough for her professionalism. Thank you Jeannette. I would recommend you to anyone with the satisfaction of knowing that you did an amazing job. Thank you.