The best places to visit in Oregon: 5 exciting itineraries
If you’re planning a visit to Oregon, it can be difficult to choose the right Oregon itinerary. Located in the Pacific Northwest, Oregon is a beautiful, yet incredibly diverse state. Within one day, you can travel from sea to mountains, from rain forest to high desert.
So with such an abundance of natural beauty to experience, you’ll want to choose an itinerary that will make the most of your time. Here are five Oregon itineraries that will help you do just that.
These five itineraries will explore Oregon’s seven wonders, the Oregon Coast, the Oregon Outback, Portland Oregon, and part of the Oregon Trail. These are the best places to visit in Oregon.
Oregon Wonders Itinerary
The Oregon Wonders itinerary covers Oregon’s wide range of climates, allowing you to experience a little of everything Oregon has to offer. This loop starts and ends in Portland.
First, see Oregon’s temperate rain forest as you drive east from Portland, through the Columbia River Gorge towards Multnomah Falls, the tallest waterfall in Oregon.
Then continue east to the beautiful Mt. Hood. Go for a hike at Mt. Hood, like to Ramona Falls. Or visit Timberline Lodge, where The Shining was filmed.
Next, travel further East to experience Oregon’s high desert. In the Wallowa Mountains, take a gondola ride from Wallowa Lake Village to the top of Mt. Howard, where you can see to the next state over.
Admire the warm colors of the Painted Hills, and go hiking or rock climbing at Smith Rock State Park.
Then, visit Oregon’s only national park, Crater Lake National Park. And finally, drive along the Oregon Coast for stunning views of the Pacific Ocean before returning to Portland.
The best time of year to plan this road trip is typically in July, August, or September, when the roads are open in Crater Lake.
However, July and August tend to be particularly hot months in Smith Rock. So it’s best to plan for an early morning hike here before the heat of the day.
Plan to spend at least ten days for this road trip. This will allow time to experience each of the Seven Wonders of Oregon, plus some travel time.
Oregon Coast Itinerary
This itinerary takes you along Oregon’s ruggedly beautiful coastline. Highway 101, also known as the Pacific Coast Highway, runs for 363 miles down Oregon’s western most border.
This road trip starts in Astoria and ends in Brookings, Oregon’s northern and southern most cities.
Along the way you’ll see 3 haystack rocks, in Cannon Beach (the rock filmed in The Goonies), Pacific City, and Bandon. You’ll visit two aquariums, in Seaside and Newport, where Keiko once lived. And visit 7 of Oregon’s 11 lighthouses.
Also, explore a shipwreck near Astoria, a ghost forest in Neskowin, and a sea lion cave near Florence. Plus, go whale watching from the world’s smallest bay in Depot Bay. Then, learn about our impact on the oceans at the Washed Ashore Art Gallery in Bandon.
And all along the way, enjoy delicious food. Many restaurants on the coast serve fresh seafood and warm clam chowder with stunning views of the ocean.
But be sure to eat at the Pronto Pup in Rockaway Beach, where the corn dog was invented! Then enjoy ice cream and squeaky cheese (cheese curds) at the Tillamook cheese factory.
You could easily travel the Oregon coast in about 8 hours if you drove straight through, but you’d miss out on so much beauty and adventure along the way. Instead, plan to spend about 1 to 2 weeks to complete this itinerary, depending on how many coastal towns you want to stop in.
Oregon Outback Itinerary
The Oregon Outback itinerary will take you to a one-horse town in the high desert of Central Oregon. This is the best itinerary to choose if you love to hike, don’t mind a little dust in your boots, and want to avoid the crowds. This is the road less traveled.
Book your stay at one of two motels in Christmas Valley. About 4 hours and 30 minutes southeast of Portland, this small town is centrally located to several amazing and unique hikes in the area.
There are three major hikes worth checking out here. First, hike through a narrow, rocky canyon at Crack in the Ground. Then, be sure to bring a headlamp to explore the depths of Derrick Cave, an old lava tunnel.
And lastly, hike the perimeter of Fort Rock, an ancient volcano, as you watch for jack rabbits sprinting across the landscape. Then visit the outdoor museum, Fort Rock Homestead Village, for a taste of what life was once like in this Wild West.
Enjoy a hearty dinner one night at the Cowboy Dinner Tree. Just be sure to reserve your seat well in advance. They may have a rather remote location, but that doesn’t mean they aren’t booked solid!
Plan to spend about five days for this road trip. That gives two full days for travel and leaves three full days for hiking and exploring Oregon’s Outback.
At the end of this vacation, you’ll have experienced Oregon, untamed and untainted in its raw and natural beauty.
Portland, Oregon Itinerary
This itinerary is all about how to spend three perfect days in Portland, Oregon. And it’s the perfect itinerary for those who prefer the city or are only able to make a short visit to Oregon.
There’s a lot more to Portland than the rain. For starters, it has a great food and restaurant scene, with a strong affinity for coffee shops and microbreweries.
Portland is also known for its love of dogs and bikes, and for its many parks, gardens and bridges. But with so much to see and do, this guide will help you see the best highlights of the city.
Day One: Start the day with brunch at one of Portland’s many delicious brunching restaurants. A few excellent options include Broder Söder, Jam Cafe, or The Tin Shed (a dog-friendly dining option!).
Then, visit Powell’s books, the largest used book store in the world. Later, enjoy a cup of tea at the Lan Su Chinese Gardens. End the day with amazing views of Portland from the Portland Aerial Tram or Tom McCall Waterfront Park.
Day Two: On your second day, set out to explore the neighborhoods, admire the street art, and eat lunch at a food truck pod. Or get outdoors and go for an afternoon hike in Forest Park to discover the witch’s hut.
Day Three: On your final day in Portland, visit the International Rose Test Gardens and the Japanese Gardens at Washington Park. Then play around at Portland’s new and interactive art museum, Hopscotch. End your trip with drinks from one of Portland’s roof top bars.
If you have extra time, you can plan a day trip from Portland. Visit the Oregon Coast, head east to Mt. Hood, or travel south to Silver Falls State Park.
Oregon Trail Itinerary
Follow the path pioneers once took through Oregon on this Oregon Trail itinerary. Walk in the deep ruts of old covered wagons and imagine what it must have been like to traverse this country before the convenience of our smooth, paved freeways.
The Oregon Trail originated in Kansas and Missouri and spanned a total of seven states. However, this road trip focuses on the stretch of trail in Oregon.
Since I-84 roughly parallels the Oregon Trail through Oregon, there are two ways to approach this road trip. Option one is to drive east on I-84 from Portland to Baker City and back again. Or, option two is to fly into Boise, Idaho, rent a car, and drive west on I-84 to Portland.
The main highlight of this Oregon itinerary is the National Historic Oregon Trail Interpretive Center in Baker City, Oregon. At the interpretive center, discover an outdoor recreation of a covered wagon camp, watch live historical re-enactments, and hike alongside wagon ruts. This site covers 500 acres and includes over four miles of hiking.
Note: The Interpretive Center is currently closed for remodeling and has moved to a temporary location. For latest updates, visit their site here.
From Baker City, follow the trail west through the Grande Ronde Valley and over the Blue Mountains. Marvel at the Columbia River as you drive through the Gorge to The Dalles, where many pioneers rafted their wagons down the river.
TIP: Other locations to hike along actual Oregon Trail ruts are at Birch Creek near Huntington and Echo Meadows near Hermiston, Oregon.
While many pioneers settled in Oregon, others continued on to Washington. However this particular road trip ends in Portland, Oregon. Plan to spend about three to four days for this road trip.
Final Thoughts on Oregon Itineraries
From ocean to high desert, from the bustling city to dusty country roads, these five Oregon itineraries are sure to have a little something for everyone.
And whichever of these itineraries you choose, you’re sure to be stunned by Oregon’s beauty and diversity.
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