: Sheep Rock Unit, John Day Fossil Beds

Your Perfect Oregon Trip, Based on Your Vacation Days

January 2, 2020 (Updated April 1, 2022)

Admit it. You need a vacation sometimes. It’s proven that taking time off can improve personal relationships, professional performance and overall health. That post-vacation bliss is real.

Yet more than half of American workers (55%) are not using all their paid time off, resulting in millions of unused vacation days. For whatever reason, Americans are not taking all their well-earned time off. The earlier you plan, the better the travel deals and the more time your manager has to prepare for your absence. Research also suggests that anticipating a vacation boosts your happiness many weeks before the trip even begins.

So what are you waiting for? Start planning your next great Oregon adventure now. (You’ll be glad you did.) Here are some trip ideas to get you started, plus a special vacation-planning tool to get your calendar ready too.

Spend your day off at Sauvie Island in the Portland Region, picking berries or pumpkins (depending on the season) and looking for wildlife.

1 vacation day

So you spent most of your accrued time off for the holidays? Not to worry, add your one vacation day to a weekend for enough time to relax and rejuvenate. Your long weekend can be spent exploring a historic Western town, cycling through the forest or just relaxing near the big city in a getaway that feels miles and miles away. Make your vacation day go far in Oregon.

A bronze statue of a rodeo cowboy stands in front of the Pendleton Round-Up.
Pendleton by Joni Kabana

Old West Weekend

For a taste of the frontier spirit, head to Pendleton in Eastern Oregon, where you can arrive via a quick flight. Located along the legendary Oregon Trail route, this historic city honors its Old West past with a modern twist. Among the bronze statues downtown you’ll find longtime craftspeople creating handmade saddles, boots, hats and fine leatherwork, as well as local tastemakers brewing up craft beer, artisan coffee and corn whiskey. Visit Tamástslikt Cultural Institute to learn about the traditions of local tribes, while Wildhorse Resort & Casino beckons for gaming and golf. Bonus points if you snag a stay during the Pendleton Round-Up, one of the 10 largest rodeos in the world.

Two cyclists look at Mt. Hood.
Oregon TImber Trail by Daniel Sharp

Bike Mt. Hood & the Gorge

Whether you’re a seasoned cyclist or an ambitious adventure-seeker, biking Mt. Hood & the Gorge belongs on your bucket list. The newest 3-mile segment of the Historic Columbia River Highway State Trail offers a scenic car-free experience. For mountain biking, the best place to learn might be the riverfront Easy CLIMB Trail in Cascade Locks. The Sandy River trail features a variety of singletrack fun. More experienced mountain bikers might take Surveyors Ridge, a challenging but rewarding 24-mile trek, or a piece of the Oregon Timber Trail Hood Tier, broken into segments of the epic south-to-north 669-mile route. Afterwards explore the region’s many urban breweries and wineries well into sundown.

A six-glass beer taster tray reveals a spectrum of yellow and orange brews.
Taster tray by Three Creeks Brewing

Beercation in Sisters

Oregon is known for craft beer for good reason, although some cities get more glory than others. Go off the beaten beer path and get your next sips in Sisters. Named for a trio of towering peaks, the city upholds a charming 1880s facade — even the local coffee shop looks like a Western movie set — with an energetic outdoorsy vibe thanks to its proximity to rivers, ski areas, golf and scenic bikeways. The town’s revered brewery, Three Creeks Brewing, starts the ultimate beercation. Try to time your visit with the Sisters Fresh Hop Festival in September or a brewers’ dinner at Three Creeks. Satisfied by suds, you’ll rest easy at one of the refined rustic retreats like FivePine Lodge or Suttle Lodge.

A woman walks on a wooden bridge.
Tsuru Island in Gresham

Getaway Near Portland

Exploring the City of Roses can easily take up your time, but there’s more to the Portland Region than its flagship city. Just outside the urban hubbub are destinations worthy of a long weekend vacation, many reachable via public transit, filled with breweries, art museums and more. Go berry picking at Sauvie Island or paddle the waters of Scappoose Bay. West of Portland, there are scenic bike routes, fabulous wineries and rockhound delights in the Tualatin Valley. Head east for serene nature parks in Gresham. A little south, you’ll find family fun in West Linn, a famous grain mill in Milwaukie and brewpubs and Willamette Falls in Oregon City. After a day of restorative exploration, treat yourself to an one-of-a-kind hotel stay like McMenamins Grand Lodge in Forest Grove.

Explore a land of lava along the McKenzie Pass-Santiam Pass Scenic Byway in Central Oregon. (Photo credit: Nickie Bournias)

3 vacation days

Now is your chance to really get to know a piece of Oregon. Are you interested in ancient lava flows? Or maybe watching a play under the stars is more your thing. Then again, there definitely days’ worth of play around Oregon’s tallest peak. And if you want to ramble around a valley known for its food — without driving — you can do that too.

Two waterfalls spill into the same volcanic crater on a blue-sky day.
Paulina Falls by USDA Forest Service

Explore Lands of Lava

Witness dramatic geologic wonders at Newberry National Volcanic Monument and Lava Lands, a 54,000-acre expanse of lava fields, basalt formations, rippling lakes and waterfalls. Fun fact: Newberry Crater is Oregon’s largest volcano. Here you can take the Trail of the Molten Land, where astronauts trained for moon landings, or walk through a lava cast forest. Go underground in Lava River Cave, Oregon’s longest continuous lava tube, or take photos at the park’s highest point, Paulina Peak. There are buttes to climb, waterfalls to find and a big obsidian flow to admire. And if your Newberry checklist is somehow accomplished in less than three days, there are plenty more attractions nearby. The charming town of La Pine makes for an easy base camp.

A stage is illuminated with a Victorian-style backdrop under open skies at sunset.
Allen Elizabethan Theatre of the Oregon Shakespeare Festival

Spotlight on the Rogue Valley

Celebrate the arts at the Tony Award-winning Oregon Shakespeare Festival, which presents eight plays from April through December. Watch shows under starry skies at the festival’s open-air Allen Elizabethan Theatre, just steps away from Lithia Park. It’s the perfect excuse to get to know more of Ashland and the Rogue Valley. Spend your next days hiking part of the Pacific Crest Trail, riding mountain bike trails, dancing at a concert in Jacksonville or wine tasting in this very special AVA. The Rogue Valley is fun for families too, with zip lines, a mysterious vortex and more. Cap off the trip by indulging in a spa day and planning your return to the Rogue Valley for a winter getaway.

Three brightly covered snowshoers smile with Mt. Hood's snowy peak in the background.
Guided snowshoe tour by MtHoodTerritory.com

Days of Play at Mt. Hood

Oregon’s tallest peak is a beacon for adventure-seekers. In winter Mt. Hood attracts downhill skiers and snowboarders and cosmic tubers to ski areas; while snowshoers, sledders and Nordic skiers flock to the sno-parks. Come summer, the landscape changes shape to the delight of hikers, mountain bikers and alpine sliders. You can easily spend three days or more here, play outside and exploring the villages and heritage sites. The journey along the Mt. Hood Scenic Byway is half the fun, and best of all, you can get to the mountain without driving now.

Sunset paints a pink sky over the woodsy city of Eugene.
Eugene by Eugene, Cascades & Coast

Car-free in the Willamette Valley

You don’t need a car to tour the Willamette Valley. Hop on a train in Portland and ride the rails to Salem, Albany and Eugene, with plenty of acclaimed restaurants and landmarks within walking distance of stations. Eugene’s walkable neighborhoods, robust bus service and bike-share program make it easy to explore the city’s eclectic shops and running history, as well as the new South Willamette Valley Food Trail. From here, take an express bus to Oakridge for forested mountain biking. For wine lovers, there’s a car-free getaway to McMinnville in the heart of wine country, with connecting buses to the Oregon Coast.

There are dozens of waterfalls in Southern Oregon, including the two-tier Toketee Falls.

5 vacation days

Road trip time! Leave your worries behind for a journey that’s long enough to make a dent in your bucket list. Go to all the waterfalls along the Rogue and Umpqua rivers (because there are a lot). Or maybe you’ll rent an RV to cruise a special part of the Oregon Coast. We dare you to play in every district of a massive national forest. Or finally venture to the Painted Hills and beyond, like you always wanted to do.

Two people walk on a wooden boardwalk through the bright red Painted Hills.
Painted Cove Loop Trail

Journey Through Time

Not many places rival the landscape of the John Day River Territory, where a mighty river sweeps past millions of years of incredible geologic history. See it all on the Journey Through Time Scenic Byway, stretching 286 miles from Biggs to Baker City and beyond. Give yourself enough time to enjoy all the stops like Shaniko, a ghost town and all three units of the John Day Fossil Beds National Monument. While many consider the Painted Hills the centerpiece of the route, other landmarks like Blue Basin fascinate geologists and photographers too. Learn about the unique scenery at Thomas Condon Paleontology Center, or explore it a ride on the Painted Hills Scenic Bikeway. And you can even dig for fossils. At the end of the byway, treat yourself to a culinary tour of Baker City.

A girl paddleboards in an ocean cove.
Southern Oregon Coast by Justin Myers Photography

Cruise the South Coast

Ready to be inspired? The scenic Southern Oregon Coast fits the bill with its secluded beaches and coastal forests. Start your trip at the Dean Creek Elk Viewing Area, then head to the Oregon Dunes National Recreation Area for hiking and ATV riding. Take the Charleston to Bandon Tour Route to get to know a trio of stunning state parks. Bandon brings fat biking and mountain biking, while Port Orford stuns with its photoworthy parks and fishing fleet. In the Samuel H. Boardman State Scenic Corridor hiking trails lead to hidden beaches. Find yourself on a jet boat in Gold Beach or under towering redwood trees in Brookings. Join a guided paddle or simply venture for a rejuvenating escape. Just be sure to indulge in the region’s flavors on the Wild Rivers Coast Food Trail.

A tall waterfall peeks between trees with its lower train falling over mossy rocks.
Watson Falls in the Umpqua National Forest

Go Chasing Waterfalls

When people think about Oregon, visions of cascading waterfalls often come to mind. Luckily, it’s easy to map out an itinerary of awe-inspiring waterfalls in Southern Oregon. With more than 15 cascades along the Rogue-Umpqua Scenic Byway, the nickname “Highway of Waterfalls” is fitting. Hike through the forest until you hear the waterfall’s roar or feel its mist. Icons like Toketee and Butte falls have kid-friendly trails with viewing platforms. Afterwards take on the Great Umpqua Food Trail or perhaps another stress-busting hike. In order to truly appreciate the scenery, tackle a waterfall or two each day with plenty of downtime and exploration in towns like Roseburg, Glide, Eagle Point, Grants Pass, Jacksonville and Medford.

A fly fisher tosses his line amid vibrant greens of the forest and river.
North Santiam River by Caleb Wallace / WVVA

A Forest of Fun

What do 1,675,407 acres of forest look like? A whole lot of fun. The Willamette National Forest is a sprawling evergreen patch with lakes, rivers and trails. Give yourself more than a day to explore each ranger district. In Santiam Canyon you can hike, cast a fishing line, go kayaking and ride a scenic bikeway to Detroit Lake. The Sweet Home area offers Nature and Heritage Tours, a waterfall loop and a historic wagon road trail. The McKenzie River Valley checks a lot of boxes: waterfalls, hot springs, mountain biking, rafting, fishing, lava fields and more. Then there’s the Middle Fork district, home to Waldo Lake, the Willamette Pass Ski Area and Oakridge, a IMBA gold-level “Ride Center.” Bring your sense of adventure.

All 363 miles of the Oregon Coast are free and open to the public — which makes for an epic road trip. (Photo credit: Kenji Sugahara)

10 vacation days

It’s the moment you’ve been waiting for — two full weeks totally disconnected from work. Now is the time to finally drive the entire Oregon coastline. Or maybe you’re ready to see the most well-known wonders. There are three newly designated Oregon Scenic Byways to explore. And if you truly want to unplug, take an off-the-grid road trip far, far away from your inbox.

A fat-tire cyclists pedals past a shipwreck on the beach.
Shipwreck of Peter Iredale by Dylan VanWeelden

All 363 Coastal Miles

You may have spend a weekend or more at the Oregon Coast — or even picked a favorite town. But have you ever dedicated a trip to traveling the entire length of Oregon’s Pacific Coast Scenic Byway? Take this 363-mile route to see why it’s so special. Along the Northern Oregon Coast, historic Astoria and local shipwrecks pique curiosity, while Seaside and the Three Capes Scenic Loop spark family fun. The Central Oregon Coast has classic beach boardwalks in Newport and Florence, plus whale- watching hot spots and the Oregon Dunes. Tour the Southern Oregon Coast for dramatic sea stacks and the temperate “banana belt” climate. Up and down the coastline, you’ll find opportunities for surf lessons, fat-tire biking, fishing trips — and more than few surprises too.

A pink sunset turns Crater Lake National Park into a dreamy scene.
Crater Lake by Dylan VanWeelden

2 Weeks, 7 Wonders

Anyone who has visited Oregon knows there are inspiring sites everywhere you go. But there are seven wonders that really stand out — and span across the state. You’ll need at least two weeks to see all seven wonders, starting on the super scenic Oregon Coast. Then venture to the brilliant blue waters of Crater Lake, the deepest lake in the nation. The spires of Smith Rock are popular for a reason; beat the crowds by riding the Sisters to Smith Rock Scenic Bikeway. Next the otherworldly Painted Hills will surely amaze. The Wallowa Mountains, called “Oregon’s Alps,” stretch 9,000 feet to the sky. The Columbia River Gorge, the largest National Scenic Area in the U.S., is home to waterfalls and forest trails. The view from Mt. Hood, Oregon’s tallest peak, is perfect for reflecting on an epic trip.

Summer Lake Hot Springs by Gabriel Amadeus Tiller

Go off the Grid

Sometimes you just feel the need to unplug from everything. Fortunately Oregon has plenty of off-the-grid experiences to satisfy those cravings. In the state’s far southeastern corner, the High Desert Discovery Scenic Byway leads to a national wildlife refuge and lava formations. The byway connects to two more: Steens Loop and East Steens, leading to the famed Kiger Gorge and Alvord Desert. In northeastern Oregon, combine the Blue Mountain and Elkhorn Drive scenic byways for ghost towns and alpine lakes. The latter connects with the Hells Canyon Scenic Byway, featuring the continent’s deepest river gorge and nine Wild and Scenic Rivers. Home to speedy pronghorns, the Oregon Outback Scenic Byway features Old West saloons, ancient caves and bubbling hot springs. Your boss won’t be able to bug you out here.

A rainbow reflects in a waterfall's cascade.
Koosah Falls along the McKenzie River Scenic Byway by Sumio Koizumi

Truly Scenic Byways

Ring in 2022 with three of Oregon’s most recently designated state scenic byways. The adventure begins in the Tualatin Valley before embarking on the Trees to Sea route through the Tillamook State Forest to the Oregon Coast. At your leisure, explore the Pacific Coast Scenic Byway between Netarts and Waldport — taking in sunrise over a ghost forest, looking for glass floats in the sand or watching baby whales play in a cove. Then take the Marys Peak to Pacific Scenic Byway to the Alsea River Valley for one of the BLM’s top mountain bike destinations. Hike Marys Peak and spend time in Corvallis to see why it’s so much more than a college town. To the southeast, the McKenzie River Scenic Byway beckons with covered bridges, waterfalls, drift-boat fishing and world-class rapids. Enjoy the steely blue waters at a riverside resort, then continue to Central Oregon and beyond.

You can hit the ski slopes of Mt. Hood for most months of the year. (Photo credit: Timberline Lodge and Ski Resort)

By season

Spring brings warm-weather hikers out of hibernation to surging waterfalls, in search of blooming wildflowers and on family-friendly treks. It’s the season for exploring the Hood River Valley Fruit Loop while still hitting the slopes. The famed salmonfly hatch brings anglers to the Lower Deschutes River. And wine lovers cheers to Oregon Wine Month. For spring break, consider taking the kids to the beautiful South Coast on an RV trip or find an easy escape with our last-minute ideas.

Summer is the perfect time for aspiring adventurers to learn new skills and relax on a guided boat trips or go underground exploring caves. Cast a line around the state on an unforgettable fishing trip. Catch a performance at the outdoor Britt Festival, or unleash your inner cowboy at a Western rodeo. Along the way find the summer ale trails. Just be sure to save up some time to make memories in the Wallowas or on a family camping trip. Most importantly, follow these easy tips on how to summer like an Oregonian.

Fall comes with a burst of colors, drawing the self-proclaimed “leaf peepers” to find the best Oregon fall foliage across the state. Your fall bucket list might include soaring over Central Oregon, attending an annual harvest festival or getting into the Spirit of Halloweentown. When paranormal activity piques your interest, tour Oregon’s haunted spots (if you dare). Come Thanksgiving start sipping at wine country open houses or take an easy family getaway to the Willamette Valley. Better yet, treat yourself to a cozy fall escape.

Winter is a favorite season in Oregon for good reason. It’s the time for sleigh and train rides and family ski trips in Eastern Oregon; when the Mt. Hood Sno-Parks become a winter wonderland, winter wildlife gathers down the Oregon Cost and you can snowshoe Crater Lake. Celebrate the holidays with Portland traditions or a ski-and-stay trip to Hood River Valley. Or hear the call of high desert retreats beckoning. When you’re ready to jumpstart your resolutions, hit a muddy mountain bike trail or book your own private fire tower lookout escape.

The Willamette Valley is home to more than 500 wineries, with tasting room events for every season.

About The

Sachie Yorck
Once Travel Oregon's Integrated Marketing Content & Community Manager and forever an Oregon enthusiast, Sachie Yorck loves telling stories that inspire meaningful travel. When in Oregon, she can be found lingering in a waterfall's mist or swirling wine at a vineyard.

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