Planning a Trip to Oregon? Use This Detailed Guide

Oregon is one of my favorite states in the country. It’s scenic as heck and incredibly diverse when it comes to its landscapes. It’s also home to Portland, a delicious city big on quirk.

If you’re planning a trip to Oregon, I’ve got you. We’ve been several times now, ticking off its coastal towns, forested parks, and scenic corridors, and just keep coming back. There’s always more to explore in the Beaver State.

Even the nickname slaps.

Quick Tips for Your Oregon Visit

Your Flight: Use Skyscanner to watch flights to the state’s biggest transportation hub in Portland. Love deals? Subscribe to Going.

Your Accommodations: Browse Booking.com or Hotels.com for your options throughout Oregon. Vrbo is my Airbnb alternative.

Your Ride: You’ll need a car to explore Oregon efficiently. Book a rental car ahead of time.

Top Spots: Find your favorite food truck in Portland, drive the Oregon coast, and take a dip in Crater Lake.

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How to Plan a Trip to Oregon

If you’re flying in from elsewhere, you’ll likely start in Portland when planning a trip to Oregon. From Portland, you’ll be well-situated for exploring along the Columbia River and Willamette Valley, and sites beyond like Crater Lake and Bend.

Here are a few more things you should know about planning trips to Oregon:

Oregon’s weather can change quickly, especially along the coast and in the mountains. Layers are essential for a comfortable trip no matter when you visit.
Unless you’re spending the entirety of your trip in Portland, a car will make your Oregon trip much more efficient. It’s a big state, and many of the highlights are spread out.
Speaking of Portland, the city is great. Oregon is known for its natural pursuits, though. You have mountains, beaches, and forests all within an accessible drive of Portland.
Wildfire season is real in Oregon and the surrounding states. If you’re planning travel in late summer or early fall, so check local reports for fire activity. The air quality may be affected, too.

A couple smiles in a coastal cottage in Oregon.

How Many Days You Need to See Oregon

If you’re visiting Portland on a city break, a long weekend will be enough to give you a taste of all that’s unique about the city.

If you’re road-tripping, I’d suggest at least a week to see Oregon’s highlights. With that much time, you can hit Portland, spend a day on the Oregon coast, and explore the state’s impressive interior.

It takes about 10 hours to drive across Oregon from the coast to the Idaho border. I wouldn’t recommend that, though. You’re going to want to stop!

The Best Time to Visit Oregon

Summer is the best time of year to visit Oregon.

Oregon’s weather can get a little wacky, so it’s hard to predict what you’ll get when you visit Oregon. Summer will offer you the best chance at sunny skies for any outdoor activities you may be planning.

If you’re a winter sports enthusiast, the winter chill may not bother you so much.

Check out more detailed information on seasonal changes in Oregon:

Summer: You’ll find higher prices during the peak summer months when the state’s natural wonders are at their best. If you’re headed to the coast, don’t expect bikini weather. Oregon’s coast is the chilliest part of the state. You can still get ice cream.
Fall: Much of the state enjoys sunny weather through the start of autumn. Wineries are in full harvesting mode, so the months of September and October are a great time to go wine tasting. November is the start of the rainy season.
Winter: Winter in Oregon is wet and cold, so if you want to get the best feel for the state, there are better times to go. Those looking for winter sports may want to visit the resorts around Mount Hood and the Mount Hood National Forest.
Spring: By mid-March spring is starting to spring, and Oregon is coming alive with blooming flowers and cultural festivals. Things are still a bit unpredictable in this timeframe, though, so pack items that you can layer.

How to Get to Oregon

You’ll likely be flying into Portland on your trip to Oregon. Once you’re there, you can connect to a variety of regional airports or grab a rental car for the rest of your journey.

Oregon lends itself to some beautiful scenic drive opportunities, for those who live in the surrounding states and would like to plan road trips.

Amtrak Cascades traverses the Pacific Northwest, too, taking travelers to Portland, Eugene, and Salem within Oregon. Check out their timetables online.

How to Get Around Oregon

If Portland is your final destination, you could get away with using the city’s public transportation. Portland has light rail, streetcars, and buses that will take you to pretty much anywhere you’d want to go in and around the city.

Note: Portland is also very bike-friendly, for those looking to burn some calories while they’re having their fun touristy times.

Otherwise, it’s just going to be more efficient if you rent a car for your Oregon adventure. So much of the best the state is off-the-beaten-path and inaccessible by bus or train.

It’s best to just rent a car from the airport upon arrival, so you’re not figuring that out when you’re ready to explore. The major airports will have all of the major car rental agencies.

Top Places to Visit in Oregon

Oregon’s best stops are wild and wonderful. From the coast to the forested interior, it’s easy to find a scenic area that speaks to you.

Oregon rewards those willing to be a little adventurous. It helps that even novice hikers can appreciate its natural wonders and waterfall chasing. Let’s explore my favorite places to visit in Oregon, from its forests to its coast.

Bend

Explore the Lava Lands area of Newberry National Volcanic Monument. Hike through the Deschutes National Forest. Stroll around the lovely Drake Park, the very place that caused me to fall in love with this town.

Note: You’ll be well-situated from Bend to explore other Oregon bucket list stops like Crater Lake National Park and Mt. Hood, as long as you make sure to give the town its due.

Bend is small enough that it’s easy to explore on your own.

If you’re looking to add a few excursions to your trip to Bend check out these options:

Coastal Oregon

An Oregon coast vacation is perfect for anyone who doesn’t love the beach. Now, hear me out. Vacations in Cannon Beach and other popular coast Oregon towns don’t have to involve sunbathing.

It’s about hiking to panoramic vistas, eating delicious food, and exploring some of the state’s best craft beer spots.

Not sure where to start?

Outside of Cannon Beach, known for Haystack Rock, or “Goonies Rock,” and Ecola State Park, Oceanside is one of my favorite places in the world. It’s quieter than more popular towns like Astoria, Newport, and Seaside, and that’s how I like it.

Columbia River Gorge

The Columbia River Gorge National Scenic Area is considered by most to be the prettiest part of Oregon. It’s known for its waterfalls, particularly Multnomah Falls, the adventurous vibes of towns like Hood River, and access to classic views of Mount Hood.

The Historic Columbia River Highway is the best way to see the highlights. The scenic byway cuts through the state’s extremes, showing off Oregon’s biodiversity.

This scenic area is easy enough to explore on your own, as long as you’ve rented a car. If you’re interested in a guided experience, check out my top picks:

Crater Lake National Park

Crater Lake National Park is one of the most impressive national parks we’ve visited. It’s also a big deal. It’s the deepest lake in the United States at 1,943 feet.

Fun fact: Yes, those waters are really that blue. They’re also cold as heck.

Don’t let that dissuade you from taking a dip. I made the mistake of walking into the water slowly to really feel the pain, but Brian jumped right in there, chilly temps be darned.

You’ll need to hike down — and then back up — to the lake to get that up close and personal, but I promise it’s worth it. Want more on available hikes while you’re there and how to make the best of your Crater Lake trip? I’ve got a Crater Lake guide.

Portland

Portland is a quirky place, and locals love their local slogan: “Keep Portland Weird.” From its tiny house scene to more food trucks than you could get through in a lifetime, Portland is always an interesting and delicious visit.

Fun fact: The city also boasts the smallest park in the country.

Mill Ends Park is essentially a tree in the middle of a median that was supposed to be the spot for a new light pole. Local lore suggests it’s now home to some leprechauns. Do with that what you will.

If you want to linger, Portland is also an excellent base for day trips. Hit up Oregon’s delectable wine country, the Oregon coast, and the Columbia River Gorge, all while staying in the city.

Interested in sticking to a Portland vacation? Explore the cities’s best gardens at Washington Park and the Portland Japanese Garden. I have a detailed Portland itinerary for more on making the most of your trip.

Portland is easy to explore on your own, even using the available public transportation while you’re there.

If you’re seeking guided experiences, though, check out some top tours around Portland:

More Places to Visit in Oregon

We’ve seen a lot of Oregon, but there’s so much more to discover. Here are a few more Oregon destinations still on our list for repeat trips to the state:

John Day Fossil Beds National Monument: If you’re a fossil nerd, this one’s for you. See over 40 millions years worth of the stuff plus access to the Painted Hills.
Smith Rock State Park: If you’re already in Bend, this one is an easy add-on to dramatic rock formations. The park is popular with rock climbers, too.
Silver Falls State Park: This one is known for the Trail of Ten Falls, a beautiful loop featuring numerous waterfalls. I’d love to see it!
Tamolitch Falls (Blue Pool): Visit the Willamette National Forest for a lovely waterfall at the end of a four-mile hike.
Umpqua National Forest: Access the Umpqua River Scenic Byway for hiking, fishing, wildlife, and hot springs.

Oregon Travel Itineraries

One week in Oregon is a good amount of time to introduce yourself to the state. Here are a few ideas for how you could spend that time:

Option 1: Oregon Highlights

Day 1: Arrive in Portland.
Day 2: Drive the Oregon Coast.
Day 3: Go wine tasting in the Willamette Valley.
Day 4: Explore the Columbia River Gorge and Mount Hood.
Day 5: Visit Crater Lake National Park via Bend.
Day 6: Explore Bend.
Day 7: Return to Portland.

Option 2: From the City to the Coast

Day 1: Arrive in Portland.
Day 2: Explore Portland.
Day 3: Explore Portland.
Day 4: Hit the road for Astoria and Cannon Beach.
Day 5: Visit Tillamook, Cape Meares, and Oceanside.
Day 6: Take a scenic drive down to Newport and Florence.
Day 7: Return to Portland.

Option 3: Outdoor Adventures in Oregon

Day 1: Arrive in Portland.
Day 2: Hike to Multnomah Falls in the Columbia River Gorge.
Day 3: Explore scenic spots around Mount Hood.
Day 4: Spend the day at Smith Rock State Park.
Day 5: Explore Bend and hike to Tumalo Falls.
Day 6: Explore Crater Lake National Park.
Day 7: Return to Portland.

Amazing Facts About Oregon

Oregon has some of the best scenery you’ll encounter while in the United States, but that doesn’t leave it immune from my fun fact-finding. Check out a few of my favorites:

Oregon’s state flag is two-sided. It’s all class on the one side, with a beaver on the other. While the state’s beaver origins are in the fur trade, the furry critters can still be found living a more peaceful existence building dams and whatnot.
It isn’t just a pixelated computer game where you try to avoid dysentery. The Oregon Trail is a real thing. At 2200 miles, it was once the longest land route in the United States.
The first one-way streets in the world were in Paris, but Eugene claims to be the first in the United States with one-way streets.
If you’ve ever insulted someone by saying they’re from Idiotville, that’s actually a real place. Idiotville is a ghost town in Tillamook County, which is also where some of the best cheese in the country is made.
Another stellar name is the Whorehouse Meadow in Oregon’s Steens Mountain Wilderness. Apparently, entrepreneurial women during Old West times used said meadow to service cattle ranchers and sheepherders.

What to Pack to Oregon

The weather in Oregon is a little silly. It can be nice and sunny in the morning and raining on you by the afternoon. That means packing for a variety of weather changes.

Check out a few ideas for what you should pack on trips to Oregon:

Flannels: Flannels will keep you warm, but they’re also basically part of the uniform in Portland. Most of you probably already own one, but I’m sure you could use more of those checkers.
Hiking Backpack: Hikers will want to come to Oregon prepared, as some of the best payoffs in the state will be at the end of a trail. Both Brian and I like the Osprey brand if that does anything for you!
Hiking Shoes: Oregon may only have one national park (Crater Lake), but that doesn’t mean it isn’t spoiled for outdoor activities. Bring along a good pair of hiking shoes that you’ve broken in already to see the best natural wonders in the state.
Layered Jacket: When you know you’re going to be dealing with unpredictable weather, pack layers. A layered jacket or shell typically includes a layer of fleece or weatherproofing underneath, giving you options depending on the temps outside.
Thermal Tops: Oregon’s wet season is long, so you’ll want to pack some layers to keep warm. Thermal tops are a good option to put underneath that flannel or sweater, or even solo under your jacket if you find a fun pattern.

Famous Foods in Oregon

Oregon is famous for the following foods:

Cheese
Craft beer
Dungeness crab
Filberts
Marionberries
Morels
Pears
Pink shrimp
Pinot noir
Voodoo Doughnuts

Special Dates & Events in Oregon

If you’re looking to visit Oregon during a certain timeframe, think about whether there are any festivals or holidays during that time. That could make or break your trip. Check online for specific festival dates.

Here are a few notable annual events:

UFO Festival: It’s not quite as big as similar events in Roswell, New Mexico, but the annual UFO Festival in McMinnville is three full days of all things UFO-related. They keep it family-friendly, though, so think costume contests and the like.
Portland Rose Festival: Roses have a storied tradition in Portland, and the annual Portland Rose Festival celebrates that. The civic festival, run by the nonprofit Portland Rose Festival Association, is also a celebration of Portland.
Oregon Country Fair: The free-spirited Oregon Country Fair is a three-day celebration of art and music held in Veneta, a town in the Willamette Valley. The organizers in charge are actually stewards of the land where the fair is held.
Pendleton Whisky Music Fest: The Pendleton Whisky Music Fest started as a country music festival. It has since attracted a more diverse group of musical acts, but don’t worry. They’ve retained the whisky offerings.
Waterfront Blues Festival: The Waterfront Blues Festival in Portland is an annual four-day event that celebrates the best of the blues scene. It’s consistently ranked as one of the best live music events in the state.

Where to Stay in Oregon

Deciding where to stay on trips to Oregon depends on your itinerary. We typically book based on a blend of efficiency and cost. Portland may seen like it’d be the most expensive, but it actually offers the most options to stretch your dollar.

Browse Booking.com or Hotels.com for your options based on your itinerary. Vrbo is my Airbnb alternative if you want something with more amenities.

Plan an unforgettable trip to Oregon.

We keep coming back to Oregon for a reason. The state is spoiled with choices when it comes to foodie adventures, outdoor adventures, and quirky adventures you won’t get anywhere else.

Despite multiple visits to the state, we’re just not done yet. I’m OK with that. I’ll happily come back for more hikes, more wine, and more of those doughnuts.

Love scenic drives? Check out these destinations:

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