I know I have said it in multiple blogs, but Oregon is my favorite state to visit in the US. It has beautiful coastlines, bountiful waterfalls, lush rainforests, delicious wine, fresh fruit, and so much more. In this 14-day Oregon road trip itinerary, you will get to see the best that the state has to offer! This is a pretty quick way to see Oregon’s highlights. You can definitely add a week or two to your itinerary and slow it down. But not all of us have the luxury of endless vacation days, so this is a great way to see as much as you can in just 2 weeks.
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14-Day Oregon Road Trip Itinerary
Oregon Road Trip Itinerary and Map
| Day 1 | Columbia River Gorge |
| Day 2 | Hood River |
| Days 3-4 | Bend |
| Day 5 | Crater Lake National Park |
| Day 6 | Umpqua National Forest |
| Day 7 | Redwood National Park |
| Days 8-11 | Oregon Coast |
| Days 12-13 | Willamette Valley and Silver Falls State Park |
| Day 14 | Portland |
Do You Need Park Passes?
There is a lot to unpack here. Most of the stops and viewpoints are part of a state park or National Park Services land, and they will require an entrance fee. In Oregon state parks, the daily parking permit is $5 per day per vehicle and are sold in the parking area of each park. Your daily park pass is good at all state parks you travel to that day, meaning you can move from park to park and only pay the one-day $5 fee. Most of the machines only take credit card, but we did find one that only took exact change cash. So I would recommend bringing both a credit card and small bills. You can also purchase an annual Oregon state park pass here for $30.
For NPS lands, you will have to pay a separate fee. If you have an America the Beautiful Annual National Park Pass (Interagency Pass) or a Northwest Forest Pass, you can display this pass on your dashboard and skip the daily fee.
Best Time to Visit
The best weather for an Oregon road trip usually happens in the summer and fall months. Summer is the busiest time of year for this area, but fall runs a close second with adults vacationing here after kids are back in school. The winters are the least crowded but also the coldest and rainiest times. My favorite time to visit is in the springtime when the crowds are pretty much nonexistent and the flowers are blooming. This time of year can also have cool and rainy weather, but I think it adds to the charm of the Oregon. Also, if you visit during April, you can make a side trip to the Wooden Shoe Tulip Festival near Salem. We did this, and the tulip fields were breathtaking.
If you are visiting between May and September, you may have to acquire a special permit for some hikes and the waterfall corridor. Information about getting a timed entry permit to Multnomah Falls and Waterfall Corridor is located here.
Know Your Tide Times
When doing any coastal trip, tide times can be very important depending on what your plans are. This Oregon road trip is no exception. Thor’s Well is best seen at or near high tide. If you show up at low tide (like I originally did), the well is less than impressive. Conversely, if you are wanting to see tide pools or beachcomb for sand dollars and other shells, you will need to arrive around low tide.
What to Pack for Your Oregon Road Trip
- Water!! I recommend bringing a refillable water bottle or two. Oregon charges a tax on plastic bottles, so it is best if you use a refillable one. Not to mention, it is better for the environment!
- Bug Spray – Keep those pesky bugs away!
- Sunscreen – Protect your skin from the sun, and do not forget to reapply.
- Hat – More sun protection to block the sun from your face, but the hat can also keep rain off your face.
- Hiking shoes/boots – These are waterproof so walking on the beach or in muddy areas will not be a problem. Here are the men‘s version of the hiking shoes I love.
- Hiking socks – The best way to prevent blisters is by keeping your feet dry. Moisture-wicking socks are the best way to do that.
- Backpack – A backpack is a necessity when hiking to carry your water, snacks, sunscreen, etc. that you may need on your longer hikes.
- RTIC Soft-Sided Cooler – Keep your drinks and food cool in this soft cooler.
- Packing Cubes – Keep your stuff organized in your luggage with these packing cubes.
- Rain Jacket – Rain can (and probably will) occur at some point while in Oregon, so make sure to pack your men’s or women’s rain jacket.
- Waterproof Pants – If visiting in the rainy season, waterproof pants will help keep your legs dry. Men’s Pants.
- Jacket – Even in warmer months, the temps can be cool so pack a light men’s or women’s jacket.
Day 1 Oregon Road Trip – Columbia River Gorge
Start your Oregon road trip driving from Portland to the Columbia River Gorge area. There are several trailheads and waterfalls along the Historic Columbia River Highway. I-84 runs parallel to the Historic Columbia River Highway and alongside the Columbia River for through-traffic. Stop at Portland Women’s Forum State Scenic Viewpoint and Vista House for panoramic views of the Columbia River Gorge.
Waterfall Corridor and Multnomah Falls
After your stops at the viewpoints, start making your way to the Waterfall Corridor. Stop at LaTourell , Bridal Veil, and Shepherd Dell Falls first. If you are unable to get a timed entry permit for the Multnomah Falls, you can still visit these three waterfalls. The next waterfall you will come to is Wahkeena Falls.
Multnomah Falls is an iconic waterfall and is Oregon’s tallest at 620 feet. Views from the base of this waterfall are located just a short walk from the parking lot. Benson Bridge crosses Multnomah Creek and is only a 0.2 mile walk from the base of the falls. However, if you want to reach the top of Multnomah Falls, you will need to walk another mile up the 11 switchbacks. After passing Multnomah Falls, you will see Horsetail Falls on the side of the road.
Wahclella Falls
If you feel up for a short, easy hike, add Wahclella Falls to your itinerary. It is my favorite waterfall in this entire area. Wahclella Falls Trail is a 1.9 mile, out and back, easy trail with an elevation gain of 223 feet. See The Best Hikes in Columbia River Gorge for more hiking options in this area.
Day 2 Oregon Road Trip – Hood River
Hood River Fruit Loop
Hood River is a small town on the banks of the Columbia River in Oregon located about an hour east of Portland. This town’s close proximity to Mt. Hood, Columbia River Gorge Scenic Area, and the Hood River Fruit Loop make it the perfect place to visit! My favorite way to spend time in Hood River is to drive the Fruit Loop and stop at all the fruit stands, vineyards, and lavender farms. Visit The 18 Best Things to Do in Hood River for ideas to plan your day.
Mt. Hood National Forest
If you are feeling up to it after a day of wining and fruiting, hike the 3.4 miles to Tamanawas Falls. Next, drive to Trillium Lake for the best views of Mt. Hood. When the lake is still, you can see a perfect reflection of the volcanic peak. Drive up to the top of Mt. Hood to see one of the few places you can ski year round. While here, check out Timberline Lodge.
Day 3 Oregon Road Trip – Bend
Bend is a cute town located in central Oregon where the terrain starts to flatten out and become more desert-like. I recommend spending 2 days in Bend and surrounding areas. Your itinerary here can vary drastically depending on what you want to do. You can spend your days shopping, sampling local brew, rafting, hiking or many other adventures. But this is how I spent my 2 days in Bend.
Smith Rock State Park
The rock faces in Smith Rock State Park are made from compressed volcanic ash formed 30 million years ago. The park hosts over a thousand bolted routes for rock climbers as well as miles of hiking and biking trails. Temperatures in this park can reach in excess of 100 F, so you will want to come here early to avoid the extreme heat. Spend the morning walking to the waters edge and watching rock climbers traverse the famous Smith Rock. Other trails you can hike include Misery Ridge and River Trail (3.5 miles) or Misery Ridge and Summit Trail Loop (6.0 miles).
Tumalo Falls
Located just 12 miles from Bend, makes this waterfall a nice escape from the bustling town. Tumalo Falls Viewpoint is just a short walk from the parking area. Make sure to walk the quarter of a mile up the trail to get a closer view of the waterfall. However, if you are looking at adding a bonus waterfall, hike the 2.0-mile, easy out and back trail to Double Falls. If the main parking lot is full, you can park in the overflow lot located 0.5 miles away.
Afternoon in Bend
Spend the rest of the afternoon shopping in Downtown Bend or Old Mill District. Visit one or two of the local breweries or local wineries and get a flight.
Day 4 Oregon Road Trip – Bend
Sahalie and Koosah Falls
Sahalie and Koosah Falls are roadside waterfalls off the McKenzie Highway are very dramatic and impressive. Each waterfall has its own parking lot, but you can hike from one to the other along the McKenzie River. If the parking lots are busy, you may want to walk the trail so you don’t have to look for a parking spot twice. The walk between the two falls is 0.4 miles, or you can do the full loop that takes you past the Carmen Reservoir, which is 2.4 miles.
Tamolitch (Blue Pools) Trail
The McKenzie River empties into this stunning, vibrant blue pool that you can swim in. The roundtrip hike to Tamolitch Falls (Blue Pool) is 3.9 miles which may seem daunting, but the hike is pretty easy until the very end. You will need to scramble at the very end to get down to the pool to access the water. It is easy to see why this is a very highly trafficked trail, and I cannot stress enough the importance of getting here early. By 10:00 am on a summer Wednesday, there was no more parking available in the designated areas. Get here early!
Spend the afternoon shopping and walking around the town of Sisters. This cute, quaint town was named for the Three Sisters, which are three very close volcanic peaks.
Day 5 Oregon Road Trip – Crater Lake National Park
Crater Lake National Park is Oregon’s only national park, and it is truly unique. This pristine lake is the deepest in America and was formed when Mount Mazama erupted and collapsed. The lake is filled solely by rain and snow. Spend the day driving the rim and pulling out at one of the 30 named and unnamed pullouts. The Rim Drive is generally open mid-July to mid-October.
The lake has two islands, Phantom Ship and Wizard Island, which you can take a boat tour to explore. While the lake has many hikes to viewpoints of the lake, you can also hike to Plaikni Falls or Pinnacles Valley to see something other than the lake. If you want to touch the water, the only way to do so is to hike the steep switchbacks of the Cleetwood Cove Trail. For more to do, visit 9 Things to Do at Crater Lake in the Summer.
Day 6 Oregon Road Trip – Umpqua National Forest
From Crater Lake travel west on N. Umpqua Highway and stop at waterfalls on your way to Crescent City. Start with 2 roadside waterfalls Clearwater Falls and Whitehorse Falls. Next, stop at Watson Falls, which is the tallest waterfall in Southwest Oregon and is a steep 0.8 miles trek. Next highway stop is Toketee Falls, which is pictured above and is only 0.8 miles round trip. This is the most popular waterfall on North Umpqua River and is truly impressive. Other waterfalls you can stop at include Fall Creek Falls (1.1 miles) and Susan Creek Falls (1.5 miles).
Continue driving to Crescent City which is a scenic drive the entire way. However, once you pass the California border, US-199 becomes extraordinarily beautiful and super fun to drive. The road winds and turns between the mountains along Smith River.
Day 7 Oregon Road Trip – Redwood National Park
Spend the day in and around Crescent City. Redwood National and State Parks surround the city, and you can spend your entire day exploring the giant trees in these park. Two short hikes not to miss are Stout Memorial Grove and Grove of the Titans. Both these hikes are on Howland Hill Road which is a 10-mile scenic drive that winds between the giant trees. Coastal Drive Loop and Newton B. Drury Scenic Parkway are two other scenic drives you should explore. While near Newton B. Drury Scenic Parkway, stop at Prairie Creek and Elk Meadow for a great chance to spot a herd of elk. Do one last easy 1.5-mile nature walk, Lady Bird Johnson Grove Trail.
In Crescent City, make sure to check out Battery Point Lighthouse which can only be accessed during low tide. Visit Oceanworld for your best chance at finding Redwood National Park and beach-themed souvenirs.
Day 8 Oregon Road Trip – Samuel H. Boardman to Florence
Start the day heading back north to start the coastal part of your Oregon road trip.
Samuel H. Boardman State Scenic Corridor
Samuel H. Boardman State Scenic Corridor is a 12-mile scenic drive on the southern coast of Oregon. Each of the stops are well-marked. Some of the most notable stops include the following:
- Lone Ranch Picnic Area
- Cape Ferrelo Viewpoint
- House Rock Viewpoint
- Whaleshead Viewpoint and Beach Access (Pit toilets)
- Indian Sands
- Natural Bridges
- Thunder Rock Cove (Secret Beach Trailhead)
- Spruce Island
- Arch Rock (Pit toilets)
Oregon Sand Dunes
The Oregon Sand Dunes cover about 40 miles of the Oregon coastline. You can stop at one of the many stopping points to watch as others play on the sand with dirt bikes, dune buggies, and sandboards. Or you can play yourself! There are lots of places where you can rent dune buggies.
Spend the afternoon exploring the town of Florence. Drive just north of the city to visit the Sea Lion Cave and Heceta Head Lighthouse.
Day 9 Oregon Road Trip – Florence to Pacific City
From Florence, drive north along the coast to get to your first stop of the day. For a detailed itinerary for the next 3 days of this itinerary, see How to Spend 3 Days on a Dreamy Oregon Coast Road Trip.
Cape Perpetua Scenic Area
The most impressive sight in Cape Perpetua Scenic Area is Thor’s Well, an old sea cave that collapsed. During high tide, waters rush up through the large natural pipeline and explode in the air. Then the water recedes back down the drainage hole and back into the ocean. You can walk right up to the well, but be careful as the sea can be unpredictable. Also stop at Devil’s Churn and Cape Perpetua Lookout while in the area.
Travel northward on the Pacific Coast Scenic Byway, and stop at the historic Newport Bayfront for some seafood and shopping.
Yaquina Head Lighthouse
Next, stop at the Yaquina Head Lighthouse which sits at 93 feet tall, making it the tallest on your Oregon road trip. Try to time your visit during low tide so you can check out the tide pools. You could spend hours exploring the micro-habitats for sea stars, urchins, crabs, and other sea life.
Keep driving north making stops at Devil’s Punchbowl which was formed millions of years ago when two sea caves eroded into one and the ceiling collapsed. As you keep driving along the coast, stop at Depoe Bay to look for whales. If you are visiting between May and December, you can also board a whale watching tour. Finish your day at Pacific City.
Day 10 Oregon Road Trip – Pacific City to Cannon Beach
Part of this day will be exploring the ocean side of the Three Cape Scenic Loop which consists of Cape Kiwanda, Cape Lookout, and Cape Meares. Stop at Cape Lookout first for a nice leisurely walk along the beach. Keep a lookout for sand dollars if it is low tide.
Oceanside and Tunnel Beach
Walk onto the Oceanside Beach and head north toward the cliff where the beach ends. Here you will find a manmade tunnel that leads to Tunnel Beach. Make sure to bring a light source with you (your camera flashlight will do) as part of the tunnel is very dark. There are some rocks you will have to traverse in this darker area before stepping out to the view you see in the picture above.
Cape Meares State Scenic Viewpoint
Cape Meares is your last stop on the Three Capes Scenic Loop. As you arrive in the parking lot, step out onto the viewing platform to see dramatic views of waves crashing into seaside cliffs. Walk down the trail towards the Cape Meares Lighthouse which was first lit in 1890. This stubby lighthouse is the shortest on the Oregon Coast. Be sure to walk the short distance to see the Octopus Tree, which is estimated to be 250-300 years old.
The next stop is the Tillamook Creamery. The self-guided tour was really interesting. At the end of the tour, you can taste 3 different kinds of Tillamook cheese, shop in the gift shop, and get a scoop of Tillamook ice cream. You may have a tummy ache by the end of your time here!
Cannon Beach and Ecola State Park
Cannon Beach was my favorite of all the small coastal towns we visited during our Oregon road trip. The town is small but provided enough cute shopping to entertain us for several hours. Cannon Beach is most famous for Haystack Rock which towers over the beach and resembles…you guessed it…a haystack.
Just north of Cannon Beach, drive the windy road through lush green forests and ferns to explore Ecola State Park. Make sure to visit Ecola Viewpoint to see Tillamook Rock Lighthouse off in the distance. Also allow time to explore Indian Beach and Crescent Beach.
Day 11 Oregon Road Trip – Astoria
In the morning, drive straight to Fort Stevens State Park and to the Wreck of Peter Iredale. Peter Iredale ran aground in 1906 where it has been decaying ever since. The earthen fort of Fort Stevens was used during the Civil War and World War II to protect from enemy ships entering the mouth of the Columbia River. The 4,300-acre parks also offers many recreational activities such as hiking, biking, camping, and wildlife viewing.
Finish the coastal part of your Oregon road trip in Astoria. We stopped at the Astoria Column, a 125-foot monument that sits atop Coxcomb Hill. Climb the 164-step spiral staircase to the top of the column for views of Astoria and the Columbia River. Make sure to visit other Astoria sights such as the Astoria Riverwalk, Flaval House Museum, and Columbia River Maritime Museum.
Day 12 Oregon Road Trip – Willamette Valley
Willamette Valley is Oregon’s main wine region and hosts over 700 wineries. This region is best known for their pinot noirs and is so vast that it is split into several subregions. For this itinerary, I recommend you pick between one of the following subregions:
- Chehalem Mountains
- Dundee Hills
- Eola-Amity Hills
- Ribbon Ridge
- Laurelwood District
All these regions are on the way from Astoria to Salem and will be good places to stop along the way. Just be careful, and do not drink and drive.
Day 13 Oregon Road Trip – Silver Falls State Park
Located in Oregon’s Silver Falls State Park, the Trail of Ten Falls is a moderately difficult hike where you get to witness ten breathtaking waterfalls. In order to see all ten waterfalls, you will have to hike the full trail, 7.4 miles. This length may be too challenging for some visitors, so there are several ways you can see waterfalls by shortening the hiking length or just walking from a parking area. Visit 8 Hiking Options for the Trail of Ten Falls for several ways to see the waterfalls.
If you visit during April, you can also visit the Wooden Shoe Tulip Festival. Even if you are not visiting in April, you can visit the Wooden Shoe Farms and try their local wine. Also nearby is the town of Salem and the Eola-Amity Hills wine region of Willamette Valley.
Day 14 Oregon Road Trip – Portland
Depending on your flight times, your last day on this Oregon road trip may just be spent driving to the Portland airport. However, if you have time to visit the city, today is the day. Stop at the original Voodoo Doughnut in Old Town for breakfast for truly unique designs and flavors. Your day in Portland won’t be complete unless you visit Powell’s City of Books and the International Rose Test Garden. If you want to see a spooky sight, hike through a dark forest to Portland’s Witch’s Castle.
You May Also Be Interested In:
How to Hike Oregon’s Trail of Ten Falls
The 20 Best Waterfalls in Oregon
The Best Day Trips from Portland, Oregon
The Best Hikes in Oregon’s Columbia River Gorge
How to Spend 3 Days in Columbia River Gorge, Oregon
The 18 Best Things to Do in Hood River, Oregon
The Ultimate Pacific Northwest Road Trip: How to Spend 1, 2, 3 , or 4 Weeks
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