You have a full day ahead of guzzling beer, sightseeing, and hiking so be sure to get an early start with some hash (not the kind you smoke) and huevos rancheros at Besaw’s, one of Portland’s classic joints. If you haven’t already, you’re going to want to buy some road munchies and a sandwich for today, so best bet is to go to New Seasons Market, a two minute walk from Besaw’s (or a one minute drive, but…come on) and grab whatever you need. Fill your tank. Get onto I-84 East. Don’t be discouraged by the urban sprawl you see while heading out of Portland. Soon enough you will be entering the Columbia River Gorge National Scenic Area, easily one of the most beautiful places in Oregon. Be sure to take in views of the Columbia River to your left while barreling down I-84, and then take Exit 17 in Troutdale onto the Historic Columbia River Gorge Historic Highway, a scenic byway built into the cliffs that winds through moss-covered forest with views of the river.
You’ll want to make a stop at Vista House in Crown Point for a couple of reasons. One: It has great views of the Columbia River that you might not see elsewhere and it’s on the damn way, so why the hell not. Two: Nevermind that you will be competing with all the other fanny-pack-garbed selfie-stick swinging narcissists for some shots of the Columbia River – it’s worth the view. Take in some views of the majestic river and the surrounding landscape of trees and mountains, then snap some photos if you wish. Have a snack. Vista House has an info desk if you want to learn more about the “Gorge” as we locals call it. There is also a downstairs section with a gift shop, in case you want to make your friends jealous by sending a postcard.
Continue east on the Historic Columbia River Highway. The byway takes you past five waterfalls: Latourell, Sheppard’s Dell, Bridal Veil. Wahkeena, and the huge-ass 620-foot Multnomah, Oregon’s tallest waterfall. So, assuming you are going to want to stop and gawk at Multnomah Falls for a bit (and I recommend you do) it’s about a 20 minute drive from Vista House. You may hit some traffic as this is a heavily traveled spot – good way to zone out for a bit and fantasize about what beer you’ll have once you reach Hood River. Find a parking spot. Then head over to the base of Multnomah Falls, the main viewing area, make your way past the 17-year-old making duck faces at her iphone, and take your photo. Find a shady spot and eat your sandwich. If you’re up for it, take a 4-mile hike starting at Horsetail Falls Trailhead (just east of Multnomah) that loops around five other waterfalls: Horsetail Falls, Ponytail Falls, Oneonta Falls, Upper Oneonta Falls, and Triple Falls. Or don’t hike and continue towards Hood River.
Head east on the Historic Columbia River Highway, and be sure to suck it all in, because you only have about 20 more minutes on the historic highway till it ends and you’re back on I-84. But whatever, even the interstate is freaking amazing and you are driving along the Columbia River the whole time, so there’s still plenty of scenery to be had. You will zip past Bonneville Lock and Dam and Cascade Locks. I recommend making a stop at Eastwind Drive-In in Cascade Locks (off exit 44) where you’ll be fed a ginormous ice cream cone. Then cruise for another 20 minutes or so to Hood River, get off exit 63, and make a right towards Full Sail Brewing Company for some beer (finally). Try and get a riverview seat as the brewery rests pretty close to the water. Order a Session IPA (or whatever strikes your fancy), sit back and get buzzy on hops. Alternatively, you can order a flight so you can taste a variety of beer flavors. Then head over to pFriem Family Brewers for a Belgian-styled pint. By this time you’re probably feeling heady, so walk your drunken ass around town for a bit and maybe visit some shops.
Take a rest at your hotel, or explore more of Hood River. Then head over to Double Mountain Brewery for some brick-oven pizza and beer. I recommend the IRA, a hoppy red ale, but all the beer here is top notch, so you can’t really go wrong. They also happen to serve some of the best pizza in the state, so that’s a must. After you’re properly fed and sloshed head to The River City Saloon for some live music. Or say fuck it and get the hell to bed because you have another long day tomorrow.
Alleviate the hangover you might have by gobbling some caffeine and cinnamon rolls at Bette’s Place. Then get onto 35 South which passses by fruit orchards, alder and cottonwood trees, and Routson County Park. If you’re feeling sprightly, you can stop for a hike at Tamanawas Falls Trailhead (30 minute drive from Hood River) , a pretty trail a little over three miles that includes a waterfall. Up to you, really depends how much you like hiking. And waterfalls. If you just feel like chilling then you want to keep going south on 35 through Mount Hood National Forest, then get on 26 West for a mile and look for signs for Trillium Lake , a scenic picnic area two miles south of 26 West. Trillium Lake is right by Mount Hood and provides a pretty awesome photo opportunity as the mountain is reflected in the water. Once that gets boring, head back up 26 West and make a right on Timberline Highway, and then a slight right onto W Leg road towards Timberline Lodge. Besides that fact that it’s a stunning hotel in Mount Hood, Timberline Lodge is where the outdoor scenes for The Shining were filmed. That in mind, take the creepy winding road up all 5, 960 feet. There will most likely be snow. Putz around Timberline Lodge for a bit, maybe visit the gift shop and buy a corny magnet.
By now it’s around noon, an appropriate time for your first beer of the day. Go to Blue Ox Bar in Timberline Lodge for an Ice Axe India Pale Ale and some lunch.Then get on 26 East towards Bend (about a 2 hour drive).
So you will be on 26 East most of the drive down. Madras is a good halfway mark if you need fuel, restroom, etc. Drive 26 East till you reach a junction for 97 South. Take 97 South. You will notice that the landscape has progressively changed from forest to high desert as you make the drive from Mt Hood. Yup, central and eastern Oregon are much more arid, so hope you like dry climates. 97 South passes Smith Rock State Park, which you definitely should visit, but not in the hot afternoon. I recommend saving it for tomorrow morning, unless for some insane reason you enjoy climbing or hiking in blistering temperatures with no shade. Rather, head straight to Bend Brewing Company, plop yourself on the patio, order a High Desert Ale, and enjoy scenic views of the Deschutes River. Afterwards, go tubing along the Deschutes, passing some bridges and rugged forest area, all while waving and displaying your stupid half-drunk smile to everyone you float by. Or walk along the Deschutes River Trail near Old Mill District, mostly shaded. Or, maybe find some rock to sit on and do your best impression of The Thinker.
After taking a rest at your hotel, head to downtown Bend and get a Black Butte Porter at Deschutes Brewery. Have another. Or five. Then head over to Drake (5 minute walk)for a burger and to sober up for a bit. If you have any energy left, contemplate whether you want another beer. Decide that you do, and walk 9 minutes to Silver Moon Brewing for a Pale Ale and live music. Then get your tired drunk ass to sleep.
Wake up super early if you still want to visit Smith Rock State Park. Hit up The Sparrow Bakery for coffee and bacon breakfast sandwich, then backtrack on 97 North and turn right into Smith Rock State park. Pay $5 for the day pass. If you’re into climbing this is your fucking paradise, what with the massive towering rock spires. If you’re not into climbing, take a leisurely stroll along the Crooked River for a half hour or so.
On the way back from Smith Rock head down to Pilot Butte State Scenic Viewpoint via 97 South (40 minute drive) and hike an easy loop trail that takes you to a lookout point with views of the Cascade Mountains. Then drive to Sisters via McKenzie-Bend Highway (20 west), which basically passes by ranches and more dry rugged landscape until you reach the Three Sisters wilderness area.
Make a stop in Sisters, a sort of kitschy but cute town with western false-front shops and restaurants. Visit Three Creeks Brewing for a Stonefly Session Ale. Might as well get lunch while you’re at it, so order an Outlaw Barbeque Burger (I mainly chose that because of the name). Then schmooze around town for a bit, visit some shops, or call your mom already because it’s been a couple days.
Get back on 20 West and follow signs for 126 East towards Cougar Dam Road. Turn on 126 East (McKenzie Highway). Continue bopping along the forested road which is hardly a highway, running alongside the McKenzie River, you’ll pass some lakes and waterfalls, which if you had planned well enough might be a nice spot to crack open a beer that you brought along. After about an hour of all this, you are coming close to Terwilliger Hot Springs, also known as Cougar Hot Springs. Because a road trip in Oregon just wouldn’t be complete without bathing in thermal water. Park in the lot, pay the $6 fee and walk ¼ mile through the forest till you come to the springs, FYI, the hot springs are clothing optional, so you’ll probably see a bunch of old naked dudes out and about. Soak for an hour or so and then on the road again, continuing on 126 West towards Eugene (a little over an hour drive), where more beer awaits.
Now that you’re in Eugene for the night, take a load off at Ninkasi Brewing Company, a community-driven brewery focused on local ingredients. Slug a Dawn of the Red IPA and then head to Falling Sky Brewing for a second and third helping of beer. Then order poutine and wings or some other grease-infested dinner to tame the alcohol. A more interesting food option would be Izakaya Meiji, an Asian fusion spot with tapas-style plates. From there decide if you want to hit up a bar and perhaps run into some degenerate university students who are probably there illegally, or you can go to bed. You’re most likely going to do the former and then regret it.
Wander over to Metropol Bakery and get a freshly baked croissant, and maybe some pastries to go. Hop onto 99 West back up towards Portland because Interstate 5 isn’t really that interesting. Drive along farms and meadows, and look for Willamette Park and Natural Area if you want to take a rest by the river. Stop in Corvallis, a nice university town with lots of restaurants and shops. You can stroll the Oregon State University Campus or explore downtown. Or drive up about 15 minutes at McDonald Dunn Forest and hike the Forest Discovery Trail, about an hour long.
Continue up 99 W for about 45 minutes. You will be passing wineries and orchards, since you’re right smack in Yamhill County, Oregon’s wine country. Take a beer/food break at The Blue Goat in Amity. Order a Heater Allen Pilsner because it’s probably the best fucking pilsner you’re going to find in Oregon. Have a sandwich with your second Pilsner. Sober up, eat a pastry you bought this morning. And then get back on the road. You still have about an hour drive to Portland.
If an hour in the car seems too long for this final stretch, stop by McMinnville on the way to Portland and explore downtown. Nice place to window shop and the like. Visit the Bitter Monk taproom and bottle shop and buy some bottles to take back. Then head on 99W until getting onto I-5 in Tualatin for the final countdown back to Portland. Once you’re back, immediately go to Breakside Brewery (Northeast Dekum St) for a Wanderlust IPA and celebrate your return. Then move onto Hopworks BikeBar (N. Williams Ave), a bike-themed brewery that’s just about as Portland as you can get.
If you liver allows, head to BTU Brasserie & Brewery for dinner, a brewpub that serves Chinese food and brews most of the beers with rice. Then walk off those beers and decide what kind of shenanigans you feel like getting yourself into for tonight. Or just say to hell with it, go to bed and pass out. But you probably won’t do that, so maybe finish your craft brew tour at Kells Brewpub(NW 21st Ave) sit your beer-bloated ass at the bar, order a Kells Irish Stout, and enjoy your final tap. For tonight, anyway.