Wandering the Western Willamette Valley with a Road Trip via Route 99W

By Annelise Kelly

Sure, you can bomb from Portland down to Eugene on I-5in less than two hours, but you miss so much when you do so. That means bypassing wineries and orchards, vineyards and farm stands, barns and cows—all reflections of Oregon’s agricultural roots.

So consider slowing down and taking it all in along Highway 99W. Even taking a straight shot adds a mere six miles and 30 minutes to the journey, but an overnight or weekend exploration along the route dives into the heart of the Willamette Valley.

With world-class wineries, cozy farm communities, small towns both sleepy and sophisticated, and lively college towns Eugene and Corvallis on route, there’s plenty to see, do, eat and drink. Here’s a three-day, two-night itinerary hitting some of the many highlights.

Before you head out, keep in mind that many of these destinations are closed at least a few days each week—so please call ahead or check online to verify hours and current status.

Day One: Wine Country Wandering and Overnight in Newberg

If you want to start with breakfast, fuel up on pastries, including gluten-free options, at Luckee Dutch in Newberg. You can also hit upscale newbie Field + Stream in Dundee for breakfast or lunch, or get some truly superior tacos at Newberg’s Dos Mundos food cart, run by an alumni of the kitchen at The Allison Inn and Spa.

Newberg’s Dos Mundos food cart has earned acclaim for its thoughtfully crafted Mexican dishes.

Hit the road for a leisurely loop around wine country to Yamhill and Carlton and back via Dundee on 99W.Sample wine from about 16 wineries at the Carlton Winemakers Studio. You might discover that the person pouring your wine made it; participating vintners take turns at the counter. Assemble a light lunch from the vending machine, which dispenses cheese, charcuterie, chocolate, and crackers. Carlton also has a cluster of good restaurants in its small downtown. Countless wine tasting opportunities await around every turn—such as Abbey Road Farm, where silos have been transformed to guest lodging (and where you can pet a goat on your visit).

Abbey Road Farm
Guests can enjoy a farm-stay experience at Abbey Road Farm, where silos have been transformed to guest lodging (and where you can pet a goat on your visit).

Enjoy some fresh air and exercise with a hike in the peaceful forest at Our Lady of Guadalupe Trappist Abbey, or splurge on a horseback wine ramble with Equestrian Wine Tours. Stop at Lafayette Schoolhouse Antique Mall and refuel with more tacos at Carniceria Abastos up the street, a bustling Latin grocery and butcher store with a terrific taco counter. Check into your restored vintage trailer at The Vintages Trailer Resort in Dayton and enjoy a bottle of the wine you bought today.

Guests can stay the night in restored trailers at The Vintages Trailer Resort in Dayton.

Ready for dinner? The celebrated Joel Palmer House in Dayton and Rosmarino Ostaria Italiana in Newberg are just two of a wealth of options. If the timing is right, squeeze in a film at the 99W Drive-In Theater.

Day Two: McMinnville to Independence

Start your day with breakfast at Morning Thunder Cafe in McMinnville, where many dishes are named after Grateful Dead songs. Wander the shops on Northeast Third Street, and check out the view from the fifth-story rooftop bar at McMenamins Hotel Oregon. Keep shopping until you’re hungry, then have an upscale lunch at Thistle, a farm-to-table gastropub.

Detour a few miles east on Highway 18 and visit the Evergreen Aviation & Space Museum, home of the Spruce Goose, or the indoor Wings and Waves Waterpark right next door. If that’s not your style, take Highway 18 south out of McMinnville and stop at the Yamhill Valley Heritage Center to see old farm and logging equipment, or the Mason-Rivera Sculpture Garden and Art Gallery.

Visitors to the Evergreen Aviation Museum tour a large, airy warehouse filled with a variety of aircraft in McMinnville, Oregon..
The Evergreen Aviation & Space Museum is a popular attraction in McMinnville.

Make your way back to Amity on 99W, and pop into the Blue Raeven Farmstand for pie and produce. Meet some friendly alpacas, shop for knit accessories, or even take an alpaca on a walk at Wings and a Prayer Alpacas, just north of Amity.

If you didn’t fill up on pie, continue south on 99W before heading east on Highway 22 for a short detour to Aspinwall’s Produce; the farm stand is known for massive and delicious ice cream treats crafted with seasonal local fruit and berries. Garden lovers, meanwhile, can head west along State Route 223 to Dallas and roam the Delbert Hunter Arboretum and Botanical Garden, where you can walk among native plants and a variety of ecosystems.

Whichever detour you chose, it’s time to hop back in the car and return to 99W for a relaxing drive south through farmland. As you approach Monmouth, turn left to head east for a detour to Independence—where you’ll check into the boutique riverside Independence Hotel. Spend the afternoon exploring small shops such as Same As It Never Was Vintage, the so-crammed-it’s-almost-funny Second Chance Books, and Melting Pot Candy. Stretch your legs in the Inspiration Garden at Mt. Fir Park, a project of local master gardeners, or walk along the Willamette River at Riverview Park.

In addition to stylish guest rooms, the boutique riverside Independence Hotel hosts a fun rooftop bar that overlooks the Willamette River.

Curious about local history? Stop into the Polk County Museum for photos, artifacts, and more dating back to the 1840s. Pick up an exquisite cupcake or a few colorful macaroons for dessert at Jubilee Champagne and Dessert. Then make your way to dinner at Territory, offering locavore fine dining in your hotel, or have upscale pub fare (along with locally brewed beer) at Grain Station Brew Works brewpub in adjacent Monmouth.

Day Three: Independence to Eugene

Breakfast is included at the Independence Hotel, but you might want a cookie or a pastry for the road from local favorite Ovenbird Bakery. Head south to Peavy Arboretum, a project of Oregon State University College of Forestry, and wander easy paths among native and introduced trees including a grove of giant sequoias. Just a few minutes south, visit Chintimini Wildlife Center, a hospital, rehab and education center dedicated to injured and orphaned animals. Book ahead for a guided tour or a small-group encounter with a Raptor Ambassador such as an owl, falcon or hawk.

Next stop, Corvallis.

Admire stately university buildings while strolling the Oregon State University National Historic District, or gaze at the Willamette River gliding by from Riverfront Commemorative Park. Attractions in town include the Hannah and Eliza Gorman House, the oldest residence in Oregon owned and established by Black pioneers. There’s also a wonderful bookstore, Grass Roots, on Southwest Second Street, an attractive avenue for window-shopping.

Riverfront Commemorative Park hosts some fun attractions for kids of all ages, not to mention outstanding Willamette River views, near downtown Corvallis. Photo by Alison Smith.

Dine in town at the Corvallis Meat Pie Shop, serving Australian savory pies with vegan options as well. On the highway south out of town, consider a stop at 4 Spirits Distillery for a meal or a whiskey flight for the non-drivers in the party—or continue to Monroe for refreshments at Long Timber Brewing.

In addition to thoughtfully crafted spirits and creative cocktails, 4 Spirits Distillery boasts a popular food menu in South Corvallis.

If you’ve been moving pretty fast, you might be early enough to enjoy an authentically rural lunch opportunity at the Stockman’s Cafe. It’s adjacent to the Eugene Livestock Auction in Junction City, so you’ll get a taste of genuine Oregon farm life along with your omelet or biscuits and gravy. For another way to taste the terroir of the land you’ve been traveling, go to the Camas Country Mill for bread and pastries, made from their own freshly milled artisanal flour, which is also for sale. Another dining option is The Cook Shack at Hentze Family Farm.

Congratulations, you’ve made it to Eugene!

If you’re not ready to hop on Interstate 5 and blast back to where you started, check into your restored Victorian bedroom at The Campbell House Inn in the walkable heart of town. Grab dinner at Rye, serving refined French cuisine and craft cocktails in a rustic-chic setting.

If you’re waking up in Eugene on a Saturday, shop handcrafted wares and eat your fill at the legendary Eugene Saturday Market. Otherwise, get your art on at the Jordan Schnitzer Museum of Art at the University of Oregon, housed in a beautiful 1933 brickwork building.

The legendary Eugene Saturday Market has been going strong since opening in 1970—and is open each spring, summer, and fall in downtown.

You can hop back on Interstate 5 and head north or south from Eugene—or, if you have a few days, return via Highway 99W and check out any stops you missed.