Best of Oregon Road Trip
Itinerary ideas for you to explore. In most cases, I would suggest a minimum of 2 nights at each location, so depending on your timeline you may want to eliminate a few destinations.
16 Places • 2 Saves • ago
Free

Destination Highlights

Depending on your timeline and desire to drive, here are some possible ideas to consider before our consultation call

Bandon
@kecia
Bandon Beach on the Oregon Coast is known for its famous rock formations jutting out of the ocean and its magical sunsets. There are miles and miles of beaches to enjoy, each sprinkled with its own dramatic boulders.
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Bandon Dunes Golf Resort
@kecia
Bandon Dunes is true to the spirit of Scotland’s ancient links. Six distinct links courses have been conceived in harmony with the natural environment. They combine with all the essential elements to reveal a new golf experience every time you play. The soul of the game resides here. Players walk. And at the end of the day, gracious hospitality comforts each guest like a warm, friendly embrace.
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Details
Tu Tu' Tun Lodge
@kecia
Nestled on the banks of the Rogue River, the dream was to create a place where people could escape to serenity, peace, share in good food and company while retiring to warmth, rest and comfort.
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Details
Samuel H. Boardman State Scenic Corridor
@kecia
Craggy bluffs, secluded beaches, and offshore rock formations await visitors along the 12 ocean-hugging miles of Samuel H Boardman State Scenic Corridor, located between Brookings and Gold Beach along Highway 101. This stretch of the highway features one turnoff after another, each with access to picnic areas, viewpoints and trailheads that connect an 18-mile segment of the Oregon Coast Trail.
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Details
Britt Festival Pavilion
@kecia
Britt Music & Arts Festival, a non-profit organization, is the Pacific Northwest's premier outdoor summer performing arts festival. Located in the historic 1850s gold rush town of Jacksonville, Oregon (USA), Britt presents dozens of summer concerts, featuring world-class artists in classical music, jazz, blues, folk, bluegrass, world, pop and country music. Britt's performance venue is a naturally formed amphitheater set among majestic ponderosa pines and native madrones on the beautiful hillside estate of 19th century photographer Peter Britt.
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Crater Lake Lodge
@kecia
Generally, it is nearly impossible to secure a reservation at this lodge, but it is well worth some persistence. Cancellations are frequent so it pays to call and check the website over and over.
Add to
Details
Crater Lake National Park
@kecia
Crater Lake inspires awe. Native Americans witnessed its formation 7,700 years ago, when a violent eruption triggered the collapse of a tall peak. Scientists marvel at its purity—fed by rain and snow, it’s the deepest lake in the USA and one of the most pristine on Earth. Artists, photographers, and sightseers gaze in wonder at its blue water and stunning setting atop the Cascade Mountain Range.
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Brasada Ranch
@kecia
Brasada Ranch is a family-friendly resort located just outside of Bend, Oregon that features luxurious accommodations, championship golf, world-class dining
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Bend
@kecia
Bend is world-famous for both its outdoor pursuits and pristine beauty. You can catch an art exhibit, dine at an award-winning restaurant, spoil yourself at one of our many spas, or trek the legendary Bend Ale Trail, the largest beer trail in the West. Bend makes a great spot for family-friendly fun as well, from boating on one of the Cascade Lakes to watching raptors soar at the High Desert Museum.
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Details
Timberline Lodge
@kecia
Built in 1937, Timberline Lodge has always been a grand refuge for visitors wanting to experience the magnificent and expansive high-alpine environment of Mt. Hood.
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Details
Hood River
@kecia
Hood River is one of the most charming towns in Oregon and offers endless outdoor adventures, thanks to its location along the Columbia River Gorge and proximity to Mount Hood.
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Multnomah Falls
@kecia
Multnomah Falls is the tallest waterfall in the state of Oregon. It is credited by a sign at the site of the falls, and by the United States Forest Service, as the second tallest year-round waterfall in the United States.
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Details
Portland
@kecia
The things you should see during a trip to Portland, Oregon depend on your interests. For first-time visitors, we recommend checking out our list of top sights and things to do in Portland, which highlights popular attractions like Powell’s City of Books, Portland Japanese Garden, Portland Saturday Market Editor's Pick Portland Saturday Market Ongoing Every Saturday, 10 a.m. – 5 p.m. Free Tom McCall Waterfront Park ADDRESS: 98 SW Naito Pkwy, Portland, OR 97204 GOOGLE MAPS Open every Saturday from March–December, Portland Saturday Market is the largest arts-and-crafts fair in the U.S. Attractions, Events, Shopping MORE ABOUT THE EVENT , Forest Park and more.
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Details

Stephanie Inn & Dining Room
@kecia
With fireplaces and views of the monolithic sea stacks rising out of the Pacific, the Stephanie Inn is the home of laid-back luxury. Relax in our beachfront reading room, connect over beach walks and forest hikes, celebrate at our award-winning restaurant and indulge yourself at our spa.
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Details
The Allison Inn & Spa
@kecia
Nestled amidst the lush natural beauty of Oregon’s Willamette Valley, The Allison Inn & Spa offers visitors an unmatched resort experience. Situated in a quaint 35-acre setting, surrounded by sweeping views of wine country and farmland, this elegant retreat is a true escape from the business of everyday life. Accommodations: Choose from 77 deluxe guest rooms and 8 suites. Jory Restaurant & Bar: The Jory is the signature restaurant at The Allison Inn & Spa, in the heart of Oregon Wine Country. The Spa: The Allison Spa boasts 12 treatment rooms, a fitness studio, indoor swimming pool, whirlpool and pool terrace.
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Details
Dundee
@kecia
The Dundee Hills are known as the heart of award-winning Oregon Pinot Noir, but there’s even more for your palette to explore. Our winemakers are obsessed with capturing the terroir of the region, offering special experiences and helping one another learn as they continue to grow their craft. From Pinot Noir to Chardonnay, from sparkling to rosé every bottle captures a special moment in time and tells a story about the place and the people who made it.
Add to
Details

* * *
CURATED BY
Are you Krampus curious? Kecia Welt loves the Krampus and exploring remote alpine Christmas markets. Over the past four years, I have explored over 30 markets in five countries. I get excited about drinking glühwein, eating kaiserschmarrn, and taking long winter hikes. Let me help you plan your next trip... Specializing in: South Tyrol, Dolomites, Italy Austria Bavaria, Germany Czechia Custom itineraries start at $50 per day Schedule a free 15-minute consultation call at https://calendly.com/thewelts/30min Join me for my next Krampus Adventure in Italy Booking now for December 2023 - Space is limited! https://krampuscurious.com/trip/6yw9rqwdczxwqz2aln6fxpqxg9ussqq DM me on Instagram (@keciawelt)
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Best of Oregon Road Trip
Itinerary ideas for you to explore. In most cases, I would suggest a minimum of 2 nights at each location, so depending on your timeline you may want to eliminate a few destinations.
16 Places • 2 Saves • ago
Free

Destination Highlights

Depending on your timeline and desire to drive, here are some possible ideas to consider before our consultation call

Bandon
@kecia
Bandon Beach on the Oregon Coast is known for its famous rock formations jutting out of the ocean and its magical sunsets. There are miles and miles of beaches to enjoy, each sprinkled with its own dramatic boulders.
Add to
Details
Bandon Dunes Golf Resort
@kecia
Bandon Dunes is true to the spirit of Scotland’s ancient links. Six distinct links courses have been conceived in harmony with the natural environment. They combine with all the essential elements to reveal a new golf experience every time you play. The soul of the game resides here. Players walk. And at the end of the day, gracious hospitality comforts each guest like a warm, friendly embrace.
Add to
Details
Tu Tu' Tun Lodge
@kecia
Nestled on the banks of the Rogue River, the dream was to create a place where people could escape to serenity, peace, share in good food and company while retiring to warmth, rest and comfort.
Add to
Details
Samuel H. Boardman State Scenic Corridor
@kecia
Craggy bluffs, secluded beaches, and offshore rock formations await visitors along the 12 ocean-hugging miles of Samuel H Boardman State Scenic Corridor, located between Brookings and Gold Beach along Highway 101. This stretch of the highway features one turnoff after another, each with access to picnic areas, viewpoints and trailheads that connect an 18-mile segment of the Oregon Coast Trail.
Add to
Details
Britt Festival Pavilion
@kecia
Britt Music & Arts Festival, a non-profit organization, is the Pacific Northwest's premier outdoor summer performing arts festival. Located in the historic 1850s gold rush town of Jacksonville, Oregon (USA), Britt presents dozens of summer concerts, featuring world-class artists in classical music, jazz, blues, folk, bluegrass, world, pop and country music. Britt's performance venue is a naturally formed amphitheater set among majestic ponderosa pines and native madrones on the beautiful hillside estate of 19th century photographer Peter Britt.
Add to
Details

Crater Lake Lodge
@kecia
Generally, it is nearly impossible to secure a reservation at this lodge, but it is well worth some persistence. Cancellations are frequent so it pays to call and check the website over and over.
Add to
Details
Crater Lake National Park
@kecia
Crater Lake inspires awe. Native Americans witnessed its formation 7,700 years ago, when a violent eruption triggered the collapse of a tall peak. Scientists marvel at its purity—fed by rain and snow, it’s the deepest lake in the USA and one of the most pristine on Earth. Artists, photographers, and sightseers gaze in wonder at its blue water and stunning setting atop the Cascade Mountain Range.
Add to
Details
Brasada Ranch
@kecia
Brasada Ranch is a family-friendly resort located just outside of Bend, Oregon that features luxurious accommodations, championship golf, world-class dining
Add to
Details
Bend
@kecia
Bend is world-famous for both its outdoor pursuits and pristine beauty. You can catch an art exhibit, dine at an award-winning restaurant, spoil yourself at one of our many spas, or trek the legendary Bend Ale Trail, the largest beer trail in the West. Bend makes a great spot for family-friendly fun as well, from boating on one of the Cascade Lakes to watching raptors soar at the High Desert Museum.
Add to
Details
Timberline Lodge
@kecia
Built in 1937, Timberline Lodge has always been a grand refuge for visitors wanting to experience the magnificent and expansive high-alpine environment of Mt. Hood.
Add to
Details
Hood River
@kecia
Hood River is one of the most charming towns in Oregon and offers endless outdoor adventures, thanks to its location along the Columbia River Gorge and proximity to Mount Hood.
Add to
Details
Multnomah Falls
@kecia
Multnomah Falls is the tallest waterfall in the state of Oregon. It is credited by a sign at the site of the falls, and by the United States Forest Service, as the second tallest year-round waterfall in the United States.
Add to
Details
Portland
@kecia
The things you should see during a trip to Portland, Oregon depend on your interests. For first-time visitors, we recommend checking out our list of top sights and things to do in Portland, which highlights popular attractions like Powell’s City of Books, Portland Japanese Garden, Portland Saturday Market Editor's Pick Portland Saturday Market Ongoing Every Saturday, 10 a.m. – 5 p.m. Free Tom McCall Waterfront Park ADDRESS: 98 SW Naito Pkwy, Portland, OR 97204 GOOGLE MAPS Open every Saturday from March–December, Portland Saturday Market is the largest arts-and-crafts fair in the U.S. Attractions, Events, Shopping MORE ABOUT THE EVENT , Forest Park and more.
Add to
Details

Stephanie Inn & Dining Room
@kecia
With fireplaces and views of the monolithic sea stacks rising out of the Pacific, the Stephanie Inn is the home of laid-back luxury. Relax in our beachfront reading room, connect over beach walks and forest hikes, celebrate at our award-winning restaurant and indulge yourself at our spa.
Add to
Details
The Allison Inn & Spa
@kecia
Nestled amidst the lush natural beauty of Oregon’s Willamette Valley, The Allison Inn & Spa offers visitors an unmatched resort experience. Situated in a quaint 35-acre setting, surrounded by sweeping views of wine country and farmland, this elegant retreat is a true escape from the business of everyday life. Accommodations: Choose from 77 deluxe guest rooms and 8 suites. Jory Restaurant & Bar: The Jory is the signature restaurant at The Allison Inn & Spa, in the heart of Oregon Wine Country. The Spa: The Allison Spa boasts 12 treatment rooms, a fitness studio, indoor swimming pool, whirlpool and pool terrace.
Add to
Details
Dundee
@kecia
The Dundee Hills are known as the heart of award-winning Oregon Pinot Noir, but there’s even more for your palette to explore. Our winemakers are obsessed with capturing the terroir of the region, offering special experiences and helping one another learn as they continue to grow their craft. From Pinot Noir to Chardonnay, from sparkling to rosé every bottle captures a special moment in time and tells a story about the place and the people who made it.
Add to
Details

* * *
CURATED BY
Are you Krampus curious? Kecia Welt loves the Krampus and exploring remote alpine Christmas markets. Over the past four years, I have explored over 30 markets in five countries. I get excited about drinking glühwein, eating kaiserschmarrn, and taking long winter hikes. Let me help you plan your next trip... Specializing in: South Tyrol, Dolomites, Italy Austria Bavaria, Germany Czechia Custom itineraries start at $50 per day Schedule a free 15-minute consultation call at https://calendly.com/thewelts/30min Join me for my next Krampus Adventure in Italy Booking now for December 2023 - Space is limited! https://krampuscurious.com/trip/6yw9rqwdczxwqz2aln6fxpqxg9ussqq DM me on Instagram (@keciawelt)
Send A Tip
Support KECIA WELT’s work.
Select your tip amount
$5
$10
$20
$50
Or type in other amount
Powered by Thatch
The home for unique & authentic travel
Powered by Thatch: Where great trips are made.
© KECIA WELT Privacy Terms