Oregon Road Trip Itinerary: A Complete Guide to Best Stops

Oregon is a dream destination for a road trip. From rugged coastlines and towering waterfalls to breathtaking mountains and lush forests, this state has it all. Whether you’re hiking in Crater Lake, exploring hidden hot springs, or driving along the scenic Pacific Coast, there’s something magical about an Oregon road trip.

I’ve traveled across Oregon extensively, discovering the best scenic routes, hidden gems, and must-see attractions. In this guide, I’ll take you on a full-loop Oregon road trip itinerary, covering everything from iconic landmarks to off-the-beaten-path destinations.

Get ready for an unforgettable adventure through the Pacific Northwest’s most diverse landscapes!

Why Take an Oregon Road Trip?

If you love nature, adventure, and scenic drives, then Oregon is the perfect road trip destination. Here’s why:

✅ Diverse Landscapes: Explore mountains, lakes, deserts, forests, and the stunning coastline—all in one state.
✅ Outdoor Adventures: Hike waterfalls, visit hot springs, and discover scenic viewpoints.
✅ Wildlife & Nature: Spot gray whales on the coast, see elk in the forests, and watch bald eagles soaring.
✅ Charming Small Towns: Experience local breweries, cozy cafes, and artsy communities.
✅ Epic Drives: Oregon is home to some of the most scenic roads in the U.S., from the Pacific Coast Highway to the Columbia River Gorge.

Ultimate Oregon Road Trip Itinerary (10-14 Days) – Where to Start & End Your Trip

• Best starting point: Portland International Airport (PDX)
• Alternative option: Start from Seattle (SEA) and drive south to Oregon.
• Recommended time: 10-14 days for a full loop itinerary.
• Best season: June to October (Summer & Fall for best weather).

Day 1: Portland to Columbia River Gorge

🚗 Drive Distance: 62 miles (~1 hour)

Start your Oregon road trip in Portland, the state’s most vibrant city, before heading east to the Columbia River Gorge, home to over 90 waterfalls and scenic hiking trails.

Top Stops in Columbia River Gorge

🌊 Multnomah Falls

Why Visit? It’s Oregon’s tallest waterfall (620 feet!) and one of the most iconic sights in the state.

• Best Photo Spot: The Benson Bridge offers a perfect viewpoint.
• Travel Tip: Arrive early (before 9 AM) to beat the crowds.

🌿 Wahclella Falls

• Why Visit? A stunning 115-foot waterfall tucked into a lush canyon.
• Hiking Distance: 1.9 miles (easy).

What’s Unique? Less crowded than Multnomah Falls!

🌉 Rowena Crest Viewpoint

• Why Visit? One of the best viewpoints overlooking the Columbia River Gorge.
• Best Time for Photos: Sunset!

Where to Stay:
🏨 Best Western Plus Hood River Inn (Riverside hotel with a hot tub).

Day 2: Mount Hood & Smith Rock State Park

🚗 Drive Distance: 152 miles (~3 hours)

Today, you’ll explore Mount Hood, Oregon’s highest peak, and the stunning rock formations of Smith Rock State Park.

🏔️ Mount Hood & Mirror Lake Hike

• Why Visit? The tallest mountain in Oregon (11,249 feet).
• Best Short Hike: Mirror Lake Trail (4.2 miles)—perfect reflection of Mount Hood in the water.
• Winter Bonus: Skiing at Timberline Lodge, the hotel from The Shining!

🪨 Smith Rock State Park

• Why Visit? A rock climber’s paradise with epic landscapes.
• Best Hike: Misery Ridge Trail (2 miles roundtrip, steep but amazing views!).
• Fun Fact: Birthplace of sport climbing in the U.S.!

Where to Stay:
🏨 Oxford Hotel, Bend (Luxury option with spa).

Day 3: Bend & Tamolitch Blue Pool

🚗 Drive Distance: 102 miles (~2.5 hours)

Bend is one of Oregon’s most fun & outdoorsy towns, offering great breweries, hikes, and stunning landscapes.

🏞️ Tumalo Falls

Why Visit? A breathtaking 97-foot waterfall.

Best Short Hike: Tumalo Falls Viewpoint (0.6 miles).

💦 Tamolitch Blue Pool

• Why Visit? One of the bluest natural pools in the U.S.
• Hiking Distance: 4 miles roundtrip.
• Pro Tip: The water is freezing (~37°F!), so don’t expect a swim!

Where to Stay:
🏡 McMenamins Old St. Francis School (Historic boutique hotel in Bend).

Day 4-5: Crater Lake National Park

🚗 Drive Distance: 102 miles (~2.5 hours)

🌊 Crater Lake – Deepest Lake in the U.S.

• Why Visit? The bluest water you’ll ever see!

Best Viewpoints:

• 🌅 Watchman Peak (Sunset Spot)
• 🚤 Wizard Island Boat Tour (Summer Only)

Fun Fact: Formed by a collapsed volcano 7,700 years ago!

🏕 Where to Stay: Crater Lake Lodge (Best lakefront stay).

Day 6-7: Umpqua Hot Springs & Oregon Coast

🚗 Drive Distance: 173 miles (~3.5 hours)

♨️ Umpqua Hot Springs

• Why Visit? Scenic natural hot springs overlooking the forest.
• Pro Tip: Expect nudists—it’s common here!

🌊 Pacific Coast Scenic Drive

• Cannon Beach (Haystack Rock).
• Oswald West State Park (Dramatic Cliffs).
• Samuel H. Boardman Scenic Corridor (Secret Beaches).

🏡 Where to Stay: Hallmark Resort, Cannon Beach.

Day 8-10: Oregon Dunes & Whale Watching

🚗 Drive Distance: 159 miles (~3 hours)

🐋 Depoe Bay – Whale Watching Capital of Oregon

• Best Time: March–October (Gray whale migration).

🏜️ Oregon Dunes National Recreation Area

• What’s Unique? One of the world’s largest coastal sand dunes!
• Fun Activity: Sandboarding!

🏡 Where to Stay: The Ocean Lodge, Cannon Beach.

Day 11-12: Return to Portland & Explore the City

🚗 Drive Distance: 82 miles (~1.5 hours)

Before ending your trip, enjoy Portland’s amazing food & coffee culture!

🍩 Must-Try Food in Portland

• Voodoo Doughnuts & Blue Star Donuts.
• Food Cart Pods (Try Pine Street Market!).
• Breweries: Deschutes, Breakside Brewery.

🏨 Where to Stay: The Nines Hotel (Luxury).

Must-See Places & Attractions on an Oregon Road Trip

An Oregon road trip isn’t complete without visiting the state’s most iconic natural wonders, scenic viewpoints, and charming towns. Whether you’re exploring the dramatic coastline, hiking through lush forests, or soaking in natural hot springs, there’s no shortage of unforgettable stops. Below are the must-see places and attractions you should include in your itinerary.

Columbia River Gorge and Waterfalls

The Columbia River Gorge is one of Oregon’s most breathtaking regions, home to over 90 waterfalls, hiking trails, and panoramic viewpoints.

• Multnomah Falls – Oregon’s tallest waterfall at 620 feet, with a picturesque footbridge that offers a stunning view. Arrive early to avoid crowds.
• Latourell Falls – A single-drop waterfall known for its striking basalt columns. An easy hike takes you closer to the falls.
• Wahclella Falls – A hidden gem, accessible via a 1.9-mile hike through a moss-covered canyon.
• Rowena Crest Viewpoint – A perfect stop for scenic photos, offering a panoramic view of the Columbia River and winding historic highway.

Mount Hood and the Timberline Lodge

Mount Hood is Oregon’s highest peak and offers year-round outdoor activities.

• Timberline Lodge – A historic ski lodge famous for its role in The Shining. It provides cozy accommodations and stunning mountain views.
• Mirror Lake Trail – A moderate hike leading to a lake that reflects the peak of Mount Hood, making it a favorite for photographers.
• Trillium Lake – A peaceful spot for kayaking, paddleboarding, and capturing postcard-worthy views of Mount Hood.

Smith Rock State Park

A rock climber’s paradise, Smith Rock State Park features dramatic rock formations, deep river canyons, and scenic hiking trails.

• Misery Ridge Trail – A challenging but rewarding hike offering breathtaking views of the Crooked River and Monkey Face, a famous rock formation.
• Canyon Trail – An easier alternative that follows the river and provides opportunities to watch rock climbers in action.

Crater Lake National Park

Crater Lake is the deepest lake in the United States, formed by a collapsed volcano nearly 8,000 years ago.

• Rim Drive – A 33-mile scenic loop offering various viewpoints of the lake’s impossibly blue waters.
• Watchman Peak – A short but steep hike leading to a fire lookout with stunning sunset views.
• Wizard Island – Take a boat tour to this volcanic island for a unique hiking and swimming experience.

Oregon Coast and Pacific Coast Highway (Highway 101)

The Oregon Coast is known for its rugged cliffs, sea stacks, and charming coastal towns.

• Cannon Beach – Famous for Haystack Rock, tide pools, and wide sandy beaches perfect for sunset campfires.
• Cape Kiwanda – A stunning beach with towering sand dunes and scenic viewpoints over the Pacific Ocean.
• Samuel H. Boardman State Scenic Corridor – A 12-mile stretch of coastline featuring natural bridges, secluded beaches, and dramatic sea cliffs.
• Depoe Bay – Known as the “Whale Watching Capital of Oregon,” offering excellent chances to spot gray whales from the shore.

Umpqua Hot Springs and Waterfalls

Nestled in the Umpqua National Forest, this area is a must-stop for those looking to soak in natural hot springs or explore hidden waterfalls.

• Umpqua Hot Springs – A series of geothermal pools overlooking the forest, offering a relaxing experience after a long drive.
• Toketee Falls – One of Oregon’s most photogenic waterfalls, known for its deep blue pool and dramatic basalt cliffs.
• Watson Falls – The highest waterfall in southern Oregon, dropping 272 feet into a lush green canyon.

Bend and High Desert Region

Bend is an outdoor lover’s paradise, surrounded by volcanic landscapes, alpine lakes, and excellent craft breweries.

• Tumalo Falls – A picturesque 97-foot waterfall, accessible by a short hike.
• Deschutes River – Great for floating, kayaking, or paddleboarding.
• High Desert Museum – A unique museum showcasing Oregon’s wildlife, history, and Native American culture.
• Bend Ale Trail – Explore some of the best craft breweries in Oregon, with favorites like Deschutes Brewery and Crux Fermentation Project.

Painted Hills and Eastern Oregon

The Painted Hills, part of the John Day Fossil Beds National Monument, offer one of Oregon’s most surreal landscapes.

• Painted Cove Trail – A short boardwalk trail allowing visitors to see the red, yellow, and gold-striped hills up close.
• Blue Basin – A unique area featuring vibrant blue-green rock formations shaped by millions of years of erosion.
• Kam Wah Chung State Heritage Site – A historic Chinese apothecary and trading post offering a glimpse into Oregon’s Gold Rush-era history.

Where to Stay on an Oregon Road Trip?

Finding the right places to stay along your Oregon road trip depends on your budget, travel style, and how close you want to be to the state’s best attractions. Whether you prefer boutique hotels, cozy cabins, or scenic campgrounds, Oregon has plenty of options.

Portland: Urban Comfort and Unique Hotels

Portland has a wide range of accommodations, from stylish boutique hotels to budget-friendly options.

• The Nines Hotel – A luxury stay in the heart of downtown with a rooftop restaurant offering city views.
• McMenamins Kennedy School – A converted schoolhouse turned into a quirky hotel with a brewery, soaking pool, and movie theater.
• Jupiter Hotel – A hip boutique hotel near Portland’s nightlife and food scene.

Columbia River Gorge and Mount Hood: Nature Retreats

For a stay close to waterfalls and hiking trails, consider these options:

• Best Western Plus Hood River Inn – A comfortable hotel on the banks of the Columbia River with scenic views.
• Timberline Lodge – A historic alpine lodge on Mount Hood, perfect for ski season or summer hiking.

Bend: Cozy Stays and Outdoor Lodges

Bend is known for its charming downtown and access to outdoor adventures.

• McMenamins Old St. Francis School – A historic boutique hotel with an on-site brewery, soaking pool, and live music.
• Tetherow Resort – A modern mountain resort with golf courses and stunning views of the Cascade Mountains.
• The Campfire Hotel – A fun, budget-friendly option with a communal fire pit and retro design.

Crater Lake National Park: Rustic and Scenic Lodging

Lodging inside Crater Lake National Park is limited, so booking early is recommended.

• Crater Lake Lodge – The best option for staying inside the park, offering lakefront views and a cozy atmosphere.
• Mazama Village Cabins – Rustic cabins a few miles from Crater Lake, perfect for those wanting a more natural experience.

Oregon Coast: Beachfront Stays

For the best views of the Pacific Ocean, consider these options:

• Hallmark Resort, Cannon Beach – A beachfront hotel with direct views of Haystack Rock.
• The Ocean Lodge – A cozy and pet-friendly option with a classic coastal feel.
• Headlands Coastal Lodge & Spa – A luxury lodge offering oceanfront dining and adventure packages.

Eastern Oregon: Lodges and Unique Stays

For those venturing to the Painted Hills or John Day Fossil Beds, lodging is more limited but still charming.

• Riverhouse on the Deschutes (Bend) – A scenic riverfront resort offering easy access to nearby nature spots.
• Wilson Ranches Retreat (Fossil, OR) – A working cattle ranch that offers a true Old West experience with horseback riding.

Best Road Trip Food & Restaurants in Oregon

A road trip through Oregon is not just about stunning landscapes and epic adventures—it’s also an opportunity to indulge in some of the best food the Pacific Northwest has to offer. From fresh seafood along the coast to farm-to-table delights in the Willamette Valley, Oregon’s culinary scene is diverse and worth exploring. Here are some must-visit food stops and restaurants along your Oregon road trip.

Portland: The Foodie Capital

Portland is known for its incredible food culture, offering everything from high-end dining to legendary food carts.

• Pok Pok – Famous for its mouthwatering Thai-style chicken wings.
• Screen Door – A must-visit for Southern-style comfort food, including its iconic fried chicken and waffles.
• Salt & Straw – An ice cream shop featuring unique flavors like honey lavender and pear with blue cheese.
• Voodoo Doughnut – A quirky Portland institution offering colorful, over-the-top doughnuts.
• Portland’s Food Cart Pods – The city has over 500 food carts, with clusters like Cartopia and Prost Marketplace offering incredible options from around the world.

Columbia River Gorge & Hood River: Farm-Fresh Goodness

The Columbia River Gorge and Hood River are home to fantastic farm-to-table restaurants, fresh cider, and locally grown fruit.

pFriem Family Brewers (Hood River) – A cozy brewery serving Belgian-style beers and upscale pub food with river views.

Celilo Restaurant & Bar (Hood River) – A farm-to-table spot specializing in fresh, locally sourced ingredients.

Solstice Wood Fire Café & Bar (Hood River) – Known for wood-fired pizzas and delicious seasonal salads.

The Fruit Loop – A 35-mile scenic drive filled with fruit stands, wineries, and cideries where you can sample the best of Oregon’s produce.

Bend: Craft Breweries and Mountain Eats

Bend is known for its thriving craft beer scene and excellent food options that cater to outdoor enthusiasts.

Deschutes Brewery – The birthplace of Deschutes beer, offering tasty pub food and local brews.

Spork – A fusion eatery blending flavors from Asia, Mexico, and Africa into creative, delicious dishes.

McKay Cottage Restaurant – A popular brunch spot featuring fluffy pancakes and incredible scrambles.

Crux Fermentation Project – A laid-back brewery with a great selection of craft beer, food trucks, and lawn games.

Crater Lake Area: Rustic Dining

Food options near Crater Lake are more limited, but there are still a few standout spots worth checking out.

• Crater Lake Lodge Dining Room – The best place for a sit-down meal inside the park, offering stunning lake views and hearty meals.
• Beckie’s Café (Union Creek) – A legendary stop near Crater Lake, famous for its homemade pies.
• Annie Creek Restaurant (Mazama Village) – A casual eatery serving burgers, sandwiches, and soups.

Oregon Coast: Fresh Seafood & Ocean Views

The Oregon Coast is famous for its seafood, with plenty of options for clam chowder, fish and chips, and freshly shucked oysters.

Mo’s (Multiple Locations) – Known for its rich, creamy clam chowder and scenic locations along the coast.

The Driftwood Restaurant & Lounge (Cannon Beach) – A cozy spot with fresh seafood and a welcoming atmosphere.

Bowpicker Fish & Chips (Astoria) – A must-try food truck serving fish and chips made from fresh albacore tuna.

Local Ocean Seafoods (Newport) – One of the best seafood restaurants in Oregon, offering freshly caught fish and an excellent waterfront view.

Willamette Valley: Wine Country Delights

Oregon’s wine country is not just about the wines—it also boasts fantastic farm-to-table dining experiences.

The Painted Lady (Newberg) – A fine-dining restaurant offering seasonal tasting menus inspired by local ingredients.

Red Hills Market (Dundee) – A casual yet gourmet stop serving wood-fired pizzas and charcuterie boards.

Thistle (McMinnville) – A farm-to-table eatery focusing on sustainable, locally sourced ingredients.

Essential Oregon Road Trip Tips

Planning an Oregon road trip requires more than just picking the best stops—it’s also about ensuring you have the right gear, knowledge, and expectations for a smooth adventure. Here are some essential tips to keep in mind before hitting the road.

1. Best Time to Visit

The best time for an Oregon road trip depends on what you want to see and do.

• Summer (June–September) – Ideal for warm weather, hiking, and beach visits. However, it’s also the busiest season, so expect crowds at popular destinations.
• Fall (September–November) – A great time for fewer crowds, stunning fall foliage, and wine country harvests.
• Winter (December–February) – Best for skiing on Mount Hood and experiencing fewer tourists, but some roads (like those in Crater Lake) may be closed due to snow.
• Spring (March–May) – Beautiful wildflowers and full waterfalls, but expect some lingering rain and muddy trails.

2. What to Pack

Oregon’s weather can be unpredictable, so packing smart is key.

• Waterproof jacket – Rain is always a possibility, especially on the coast.
• Hiking shoes – Travel Essentials for exploring Oregon’s many trails and waterfalls.
• Layers – Mornings and evenings can be chilly, even in summer.
• Reusable water bottle – Many trailheads and visitor centers have refill stations.
• Bug spray – A must for hiking in forested areas during summer.
• Road trip snacks – Stock up on healthy and energy-boosting foods like granola bars, fruit, and nuts.

3. Renting a Car vs. Campervan

Your vehicle choice depends on the type of experience you want.

• Car rental – Ideal if you plan to stay in hotels, lodges, or Airbnbs.
• Campervan or RV – Perfect for those who want a more flexible itinerary and enjoy camping. Companies like Escape Campervans and Cruise America offer rentals.

4. Road Safety and Driving Conditions

Oregon has diverse landscapes, and road conditions can vary.

• Drive carefully in winter – Snow and ice can make mountain roads hazardous. Always check weather conditions and carry tire chains if required.
• Watch for wildlife – Especially when driving through forested or rural areas.
• Gas stations can be sparse – Fill up your tank before heading into remote areas, especially in eastern Oregon.
• Oregon has no self-serve gas stations – Attendants will pump your gas for you in most areas.

5. Camping and Lodging Considerations

If you plan to camp, make sure to book ahead during peak seasons.

• State park campgrounds – Some of the best places to camp, offering facilities and great locations. Book in advance through Oregon State Parks’ website.
• Dispersed camping – Available in national forests for a more rugged experience, but be sure to follow Leave No Trace principles.
• Hotels and lodges – Book accommodations early, especially near Crater Lake, the Oregon Coast, and Bend.

6. National Park and State Park Fees

Many of Oregon’s natural attractions require an entrance fee or parking permit.

• America the Beautiful Pass – If you plan to visit Crater Lake National Park or other federal lands, this pass can save you money.
• Oregon State Park Pass – A great investment if you plan to visit multiple state parks.

7. Be Prepared for Limited Cell Service

Some areas, especially in national forests and remote coastal stretches, have limited or no cell reception.

• Download offline maps – Google Maps allows you to download maps in advance.
• Carry a physical map – Oregon’s scenic routes can be confusing, so having a backup map is helpful.

8. Respect the Environment

Oregon is home to stunning natural landscapes, and it’s important to protect them.

• Pack out what you pack in – Never leave trash behind.
• Stay on designated trails – To prevent erosion and protect native plants.

Follow fire restrictions – Oregon is prone to wildfires, so always check fire regulations before setting up campfires.

Chanin

Chanin is a seasoned traveler and digital nomad who has lived in various states across America, immersing herself in diverse cultures and experiences. Her passion for exploration and storytelling makes her an expert in uncovering the unique charm of every destination. As a writer for Wavy Destinations, Chanin shares her firsthand knowledge and insights on the best places to visit, hidden gems, and tips for making the most out of every journey.
Her writing not only inspires wanderlust but also offers practical advice for travelers seeking authentic and memorable experiences.