Pack your raincoat and your gum-boots, you’re going to make a splash in the Pacific Northwest, with this Oregon road trip itinerary for winter. Spend some time by the dramatic Oregon coast before circling inland for some high desert fun (and blue skies, fingers crossed).
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Table of contents
General Oregon road trip itinerary notes
- Driving distances and times are meant as a guide. These estimations are based on travelling straight through without stopping.
- The best place to find bathrooms along the way is at the various State Parks. These tended to be the most reliably open and maintained public restrooms.
- Winter days are short, so plan to be on your way by 8 or 9am, as the sun will be gone again by 5pm.
- Oregon whale season peaks between mid-December and mid-January, so keep a lookout! Approximately 20,000 gray whales migrate between Alaska and breeding lagoons in Baja California, Mexico – the coastal waters are their highway. Humpbacks, orca’s and blue whales may also be sighted.
- Winter conditions cause road closures or dangerous conditions. Check road conditions for your trip at Trip Check and get details on Oregon’s traction tyre and chain laws here.
Oregon road trip itinerary
Day 1
Day one is simply making your way to your starting point for the trip: Astoria, Oregon a 1hr 50min drive from Portland and about 3hrs 25min from Seattle.
If you are travelling from further afield into Portland International Airport (PDX), you will find direct flights from many cities including Los Angeles, Denver, Salt Lake City, Albuquerque, Houston, St Louis, Chicago, Boston, NYC, Atlanta, Orlando and more.
Spend the night in Astoria. We stayed at the Holiday Inn Express for our brief visit.
Driving distance: Driving distance depends on your starting point.
Day 2
It’s here in Astoria we connect with the Pacific Coast Highway aka U.S. Route 101. We’ll be following the 101 for the first half of your Oregon road trip, taking the occasional detour or diversion. There are going to be lots of sights along the way and we can’t squeeze them all in, so I’m going to recommend some highlights. On today’s leg between Astoria and Lincoln City, I suggest:
- Fort Stevens Park right outside Astoria for the Civil War-era earthen fort on the west coast, WWII gun battery and historic Peter Iredale Shipwreck if the tide is low.
- Ecola State Park for Goonies movie shooting locations and supreme coastal views. You might even spot a migrating grey whale. Ecola State Park requires a $5.00 day-use fee.
- Cannon Beach, for the first sea stack dubbed “Haystack Rock” (yes, there are three Haystack Rocks in Oregon and you will see them all with this itinerary). Due to the houses, resorts and public property built right up to the shore, the best public access to the beach with parking and views of the rock are on the south side of town at Tolovana Beach State Recreation Site. Here you will find plenty of public parking and can walk back up the beach towards the rock formation.
- Hug Point State Park on a calm day at low tide has rock pools, sandstone caves and a seasonal waterfall to explore. Unfortunately, we experience gale-force winds and high tide, so no lovely pictures to share.
- Tillamook Creamery is a worthwhile stop for ice cream or a grilled cheese sandwich. There are no dairy tours due to the pandemic, but you can pick up Tillamook products and merchandise at the gift store.
- Three Capes Scenic Route will take you down to Pacific City via lighthouses, rocky headlands and Oregon’s second Haystack Rock standing offshore at Cape Kiwanda.
Spend the night in Lincoln City. We stayed at the Best Western Landmark Inn and have no reservations in recommending it for those looking for comfortable, mid-range budget accommodation.
Driving distance: Astoria to Lincoln City is roughly 174km (108mi), 2hr 32min.
Day 3
Departing Lincoln City, we continue on our Oregon road trip down Highway 101 to Bandon. The road out of town skirts the scenic Siletz Bay National Wildlife Refuge which is a great start to our journey. Continue south on the U.S.-101. My day three recommended stops are:
- Boiler Bay Scenic Viewpoint is a cool place to make a brief stop and watch huge swells come in after a storm or high winds.
- Depoe Bay lays claim to the “world’s smallest natural, navigable harbour” covering just 6 acres, with an opening of only 15m (50ft) and is a lovely seaside town to take a short walk along the promenade where you might see or be soaked by the fishing village’s spouting horn, where a small underwater cave funnels incoming waves straight up into the air, dousing pedestrians. Depoe Bay also has a Whale Watching Center with information and binoculars to help you spot the migrating mammals. Note: The Whale Watching Center is currently closed due to the pandemic, but there is informational signage outside the Center which you may find helpful.
- Cape Foulweather is a terrific viewpoint of the surrounding coastline at 152m (500ft) high.
- Devil’s Punchbowl State Natural Area is named after collapsed sea caves formed a natural, circular colonnade. At high tide, you can watch the waters froth and foam as the waves fill and the inside of the Punchbowl. On a low tide, it may be safe to walk inside the rock formation and explore the tidal pools.
- Seal Rock for sea lion spotting and various coastal rock formations.
- Devil’s Churn Scenic Overlook for frothy water-works as waves tear down this narrow chasm. There are a few 15min parking spots if you want a quick look, or $5 day-use fee if you want to stay longer and maybe do some hiking along the short trails.
- Cape Perpetua Scenic Area is the place to enjoy Thor’s Well, Cook’s Chasm, tidal pools, spouting horns and more.
- Heceta Head Lighthouse State Scenic Viewpoint offers provides views of the Lighthouse on one side and historic Cape Creek Bridge on the other from a quaint beach.
- Lighthouse and Sea Lion Beach Vantage Point is a stop with views of Heceta Head Lighthouse across the bay. Also, look straight down to the rocks below where you may spot a large colony of sea lions.
Spend the night in the town of Bandon. While the Best Western Face Rock Inn is a little out of town, it has the advantage of a lovely, quiet position opposite the beach, halfway between Haystack Rock and Face Rock.
Driving distance: Lincoln City to Bandon is roughly 234km (146mi), 3hr 11min.
Day 4
Spend the morning exploring the stunning rock formations and beautiful beaches of Bandon such as Oregon’s third Haystack Rock, Face Rock State Scenic Viewpoint and Coquille Point. After lunch, continue on your way to Crescent City stopping at places such as:
- Meyers Creek Beach Viewpoint an easy place to pull over and have a picnic with a view.
- Samuel H. Boardman State Scenic Corridor which encapsulates the following:
- Arch Rock natural rock formation
- Natural Bridges Viewpoint for more stunning rock formations
- Cape Ferrelo Viewpoint where you can hike a loop trail to the end of the Cape
Spend the night in Crescent City.
Driving distance: Bandon to Crescent City is roughly 175km (109mi), 2hr 10min.
Detour >> Redwoods National & State Parks, California
If you have an extra couple of days, I recommend using this opportunity to duck into California and visit the coastal redwoods. Just insert this itinerary between Day 4 and 5 of your Oregon road trip.
Day 5
Day five and six are less sightseeing and more about getting over the Cascades safely so we can enjoy some time in eastern Oregon where hopefully the sky is blue relative to the rainy west.
We originally planned to go via Crater Lake but after huge snowstorms, many of the roads were closed, so we crossed Grants Pass to Klamath Falls. Check road conditions before you attempt to cross the Cascades.
White City/Medford has various options if you need to stop for lunch. If the weather is fine, take a leg-stretcher at Lake of the Woods for scenic mountain lakes surrounded by forest.
Spend the night in the town of Klamath Falls.
Driving distance: Crescent City to Klamath Falls is roughly 234km (182mi), 3hrs 33min.
Day 6
On day six, drive Klamath Falls to Bend. Take a side trip into Deschutes National Forest to the Lava Butte Cinder Cone just outside of Bend. Here you’ll get panoramic views of the Southern Cascades and surrounding high desert.
Spend the night in the town of Bend.
Driving distance: Klamath Falls to Bend is roughly 293km (145mi), 2hrs 55min.
Day 7
Today is devoted to exploring Smith Rock State Park. Rock climbers get ready, this is your day! For the rest of us there are stunning hikes in and around the river canyon. I recommend starting with everyone’s favourite trail, Misery Ridge. Yes, the hike is moderately difficult but it’s so worth it for the view from the 1024m (3360ft) summit.
Spend the night in the town of Prineville. We stayed at and recommend the Best Western Prineville Inn for a clean and comfortable stay.
Driving distance: Bend to Prineville is roughly 73km (45mi), 1hr 5min.
Day 8
On our way to Hood River, we will make a detour to the beautiful Painted Hills. These colourful clay hills were formed millions of years ago when the area was a river floodplain. The coloured bands result from climate change from wet tropical to cool and dry. Their layers have since been exposed by erosion.
Spend the night in the town of Hood River. Here we stayed in the Holiday Inn Express and Suites and appears to have undergone a recent refurbishment.
Driving distance: Bend to Prineville is roughly 73km (45mi), 1hr 5min.
Day 9
Finishing up our Oregon road trip, we explore the dramatic beauty of the Columbia River Gorge, taking the Historic Columbia River Highway. Contrary to what TLC sang, go chase some waterfalls such as the Insta-favourite, Multnomah Falls and many others.
We end our road trip on the road back to Portland and Seattle.
Driving distance: Hood River to Portland is roughly 106km (66mi), 1hr 5min.
Recommended places to eat & drink
- Insomnia Coffee, Cannon Beach (coffee)
- Tillamook Creamery, Tillamook (lunch)
- Dory Cove, Lincoln City (lunch or dinner)
- Broken Anchor, Bandon (lunch or dinner)
- Bandon Coffee, Bandon (coffee)
- Umi Sushi, White City (lunch or dinner)
- Mellelo Coffee Roasters, Medford (coffee)
- Enoteca, Crescent City (lunch or dinner and coffee)
- Friends Espresso, Prineville (coffee)
Oregon road trip map
Use this guide to tailor yourself a super winter Oregon road trip. Please leave any feedback or questions in the comments below.
Peace, love and inspiring travel,
Madam ZoZo
