People ask us fairly often whether they can string the homes together into one trip, and the honest answer is that an Oregon road trip from the coast to Mt Hood is one of the better weeks you can spend in this state. The distances are manageable, the scenery changes every hour, and you end up with a beach, a forest and a mountain in the same set of photos. This is roughly how we do it, in the order we'd do it, with the stops we keep coming back to.
Eugene to Neskowin, through wine country
Leave Eugene mid-morning with coffee and take 99W north instead of I-5. It's slower, and that's the point. You roll through Monroe and Corvallis and into the vineyards around McMinnville, and if it's after noon we usually stop somewhere along the way for a tasting and lunch before cutting west on Highway 18 through Grand Ronde. The last stretch drops you out of the Coast Range at Otis and onto 101, and Neskowin is a few minutes north. Budget three hours if you stop, two and a half if you don't. Pick up groceries in Lincoln City or at the market in Pacific City before you arrive; Neskowin has a small store and not much else, which is exactly why we like it. The Weekender is our first night here, wood stove going by dark.
Neskowin to Manzanita, slowly, on 101
This is only about an hour and a half of driving, so give it the whole day. Check the tide table before you leave: the Neskowin Ghost Forest shows itself at low tide, and Proposal Rock is a short walk from the cabin. North of town, pull off at Pacific City to watch the dory boats launch and land at Cape Kiwanda, then sit on the deck at Pelican with a beer before continuing. Tillamook is the obvious stop for the creamery, and we still stop, mostly for the ice cream line. Past Nehalem the road bends around the bay and you'll see Neahkahnie Mountain before you see the town. Manzanita is one good street, Laneda, and the beach is at the end of it. We stay at Puffin Lane with the upstairs windows facing the mountain and the cedar hot tub ready for the fog to roll in. Our Manzanita notes cover Oswald West and Short Sand Beach, which is the hike to do the next morning.
Manzanita to Mt. Hood Village on 26
Highway 26 runs from just north of Cannon Beach straight through the Coast Range, across the Portland metro, and up into the foothills toward the mountain. It's the longest leg, around three hours without traffic, and Portland is the traffic. We try to leave the coast by nine and hit the city before lunch. If you need a break, the Sunset Highway has plenty of pull-offs in the trees, and once you're past Sandy the road narrows and the firs get taller. Welches is where you stock up; there's a decent grocery and it's the last real one. Then it's a few minutes to Wildwood Basecamp, where the first order of business is always the screened porch and the fire table. If you've been sleeping by the ocean for three nights, the quiet of a forested acre is a real shift.
Mt. Hood back to Eugene, two ways
The fast way is 26 west to I-205, then I-5 south, about three hours. The good way, from late June into October, is south through Government Camp on 35 and then 26 to Highway 20 and 22 over the Santiam Pass, or if the McKenzie Pass on 242 is open, that one. The old lava fields at the top and the descent along the McKenzie River into Springfield are as pretty as anything on the coast, and there are a dozen places to stop and put your feet in the river. In winter, stick to the interstate and check TripCheck before you leave; the passes close and chains are required more often than people expect. We end in Eugene at the Eugene House, where the yard is fenced, the trail out the door leads to a bakery, and nobody has to unpack in a hurry.
A few things that make the whole trip easier
Go coast first if you can. Coast weather is most reliable in September and early October, and the mountain is good almost any time. Keep a paper map in the glovebox; cell coverage drops in the Coast Range and on the east side of the mountain. Pack layers rather than outfits, because you will be in fog, sun, and forest shade within the same afternoon. Bring water shoes for the rivers and a headlamp for the hot tub. We travel with our dog, and all three of these stops are set up for that, with a note that Puffin Lane is the exception. And leave one afternoon in each place with nothing planned. That's usually the one people talk about later.
If you'd rather we help you line the dates up, call or email us. We've driven every one of these roads more times than we can count, and we're happy to tell you where the good coffee is on each leg. All the homes are on our rentals page if you want to start there.