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Road Tripping Through Oregon


Written by
Julie Arnan

Road trip season is fast approaching. For those of you taking the long road south to California with a little extra time built in for the trip down, the I-5 corridor through Oregon is full of enticing side trips. Who knows, maybe the side trips will become the main event. Oregon’s pine-scented grip holds on tight once a traveler gets a whiff of what this state has to offer.


Northern Oregon: Oregon City and Salem

Let’s just assume that you’re going to roll right through Portland this time around—besides, Portland could take up several articles of its own. Incorporated in 1844, Oregon City, just southeast of Portland on I-205, has high historical status as the official end of the Oregon Trail. Because Oregon City comprises three terraced levels, the city installed the Oregon City Municipal Elevator—one of only four in the world and the only vertical street in the country. The trip, which used to take up to five jolting minutes in 1915, now takes about 15 smooth seconds.

Willamette Falls solidly checks the town’s “scenic” box. The waterfall is 42-feet high and 1,500 feet wide with one of the largest volumes of water tumbling over the edge in the United States. There are viewpoints and even a museum, but the coolest way to see the falls is with an eNRG Kayaking guided tour. The 90-minute tours are available by appointment and have four daily start times.

Food and Drink

The downtown Main Street corridor features indie boutique clothing retailers (Denim Salvage, the Refinery), food and wine bars (Nebbiolo Wine Bar & Market) and, just a touch farther afield, breweries. Oregon City Brewing is the first brewery in town since the days of Henry Weinhard in the late 1800s. Try the bold, hoppy Clackamas River Red or the Elevator IPA showcasing a restrained hand on the piney flavor often overdone by PNW brewers. Excellent beer and full-album vinyl ambiance are complemented by a new in-house partner with OP Wurst in the brewery kitchen. Dubbed the “frankfurter mastermind,” Victor Deras of Portland’s Olympia Provisions displays his meaty creativity with what is, frankly, an astounding variety of not-your-average hot dogs perfectly paired with a cold brew. OCB isn’t the only brew game in town, however. Feckin Brewing near the Willamette River overlook offers Irish-style beers on tap with live music on Friday and Saturday nights.

Try the Feckin IRA with a slightly bitter coffee finish.

Cruise Down to the Capital

Oregon’s capital has a laid-back midcentury aesthetic—the historic downtown features brick facades and several vintage theaters of which some have been converted into restaurants and other businesses. Stop for a lunch bite at table FIVE 08, a French dinner at Crooked House Bistro, or any time of day or night at the Kitchen on Court Street. Catch a ride on the Willamette Queen sternwheeler from Salem’s Riverfront Park, also home to a huge open lawn used for concerts and festivals in the summer months and an indoor carousel open year-round. The city converted an old railroad bridge into a pedestrian path across the river connecting the Riverfront Park with the Wallace Marine Park to the northwest. Another pedestrian bridge is currently under construction at the south end of the Riverfront Park that will connect it to Minto-Brown Island Park to the southwest—a 1,200-acre lush nature preserve with 19 miles of trails and even a 30-acre off-leash dog park.

Gardens and a Theme Park

Salem’s surrounding countryside supports growth of all kinds from flowers and wine grapes to children’s imaginations. The Oregon Garden in Silverton is an 80-acre space featuring 20 specialty gardens, open year-round. Lodging and on-site dining make it the perfect layover destination—especially in June when they host Brewfest during Father’s Day weekend. The historic Deepwood Gardens created by female landscape architects Elizabeth Lord and Edith Schryver in the 1930s boasts 4.5 acres of lush English-style gardens. Stop by June 24 for the annual Wine & Jazz Fest. Young children needing a break from a long car ride won’t miss the sign for Enchanted Forest just south of Salem. This eclectic homegrown theme park, conceived by sculptor Roger Tofte in the 1960s and opened in 1971, has everything from Storybook Lane to Old European Village, Tofteville Western Town to Bumper Boats.

Wine Country

Hop the Willamette River for access to the Eola-Amity Hills AVA vineyards and wineries. This region’s wines are heavily influenced by the cool marine air flowing through the Van Duzer Corridor that significantly lowers evening temperatures in the summer months. Bethel Heights Vineyard features block-designated Pinots grown on some of the area’s oldest vines. Other not-to-miss nearby wineries include St. Innocent Winery, with a philosophical focus on food-wine pairings, and the appointment-only Walter Scott Wines featuring Burgundy varietals that showcase the elegant high-acid potential for wines produced in this AVA.

Recommended wines include the St. Innocent 2014 Freedom Hill Vineyard Chardonnay (honeysuckle, pineapple, baking spice), the 2013 Zenith Vineyard Pinot Noir (currants, mushroom, dark cherry, hint of smoke) and Walter Scott 2015 X Novo Chardonnay (lemongrass, green banana, ginger).


Central Oregon: Eugene and Cottage Grove

Smack in the middle of Oregon’s I-5 corridor lies Eugene—home of the Oregon Ducks (University of Oregon). The city vies with Salem as the state’s second-largest population center, but clearly pulls ahead in terms of choice dining and drinking establishments. Visit the Whiteaker neighborhood, which is easily missed if you exit I-5 and head downtown. Stay at the Inn at the 5th—a boutique hotel tucked into a collection of unique retail options, including Provisions Market Hall and Marché restaurant.

Fermentation District

Though not the first brewery in town, Ninkasi put Eugene on the beer map with its flagship Total Domination IPA in 2006—a prophetic moniker considering the brewery production went from 1,500 to 105,000 barrels in just 10 years. All that growth prompted the need for huge new facilities, much of which are open to the public through daily tours. If you like massive hoppy IPAs, Ninkasi delivers in a big way. Otherwise, skip the IPAs in favor of the Pacific Rain Pale Ale or the Believer Double Red Ale. Ninkasi’s success has worked like a catalyst in the neighborhood, ushering in a thriving indie culinary scene—Grit, Rye, Papa’s Soul Food, Izakaya Meiji and Pizza Research Institute to name a few. Grab an Ale Trail passport (available at the Adventure Center just off I-5 in nearby Springfield) and start exploring Eugene’s craft beer scene a pint at a time. Don’t miss a stop at Falling Sky Brewing House. The décor affects a mellow don’t-mind-me act belying the fact that this place has won more “Best of” awards than Meryl Streep. The current tap list regularly runs 15 deep (in 2015, they brewed something like 95 different recipes), and the food goes way beyond burgers and pretzels. Everything is made in-house from the bread to the pastrami and the house-cured vegetable pickles to the smoked meats and cheeses. Take the night over the top with a stop at Sweet Life Patisserie—pies, cookies, brownies, macarons, petit fours, cakes—oh my!

The Scenic Tour 

Head south for a two-wheeled sightseeing adventure through Cottage Grove’s Covered Bridges Scenic Bikeway. The 36-mile loop begins and ends near Main Street, passes by six historic covered bridges and traverses along creeks, with some steep portions to get to Wildwood Falls. For the easier family-friendly version, ride through the Row River Trail portion to the southern end of Dorena Lake and back. After you’ve worked up an appetite, drive back to Creswell Bakery—a few blocks west of I-5 in the town of Creswell. Head west out of town on Camas Swale Road to connect up with Territorial Highway where several wineries are located, including Iris Vineyards, Silvan Ridge Winery and the state’s largest single producer of Pinot Gris at King Estate—a certified biodynamic winery with a beautiful facility and restaurant perched atop a hill like a golden beacon of viniculture. When in Pinot Gris country, try the King Estate 2015 Domaine Pinot Gris (supple with honeysuckle, white flowers, pineapple). 


Southern Oregon: Medford, Jacksonville, Ashland and Beyond

Don’t make the mistake of cruising through southern Oregon without planning a few stops. Start with a tour through Medford’s Harry & David factory and watch hundreds of pounds of butter and sugar enrobe fluffy popcorn in caramel sauce or the company’s signature creamy Comice pears sorted for holiday gift baskets. Newly opened Pallet Wine Company is a great place to try a variety of regional wines, made under the guidance of owner Linda Donovan. 

Trifecta of Yumminess in Central Point

By no means a metropolitan area, Central Point, just north of Medford near the airport, has a one-stop corner of delicious treats at the Artisan Corridor. After tasting the cheeses at the Rogue Creamery, order a life-changing grilled blue cheese and honey sandwich and walk next door to Ledger David Cellars for an excellent wine pairing—sublime with the 2015 Radiant White (full-bodied with mango, caramel, bright acid). After a decidedly unsnobby conversation with Robert, the tasting room manager, while trying wonderful southern Oregon wines, walk across the parking lot to the lilac-colored building housing Lillie Belle Farms Handmade Chocolates. The shelves are bursting with creatively crafted chocolates—tiny chocolate martini cups with hand-rolled marzipan olives, beautifully swirled bonbons, bars and hilarious voodoo bunnies. Hopefully, chocolate maker Jeff Shepherd will be milling about. You’ll know him by his wildly printed Hawaiian shirt, ponytailed locks and giant smile from his “all-consuming passion for all things cacao.”

Charming J’Ville

Once upon a time, Jacksonville was the largest town in southern Oregon thanks to the local gold rush. But, when the gold ran dry and the railroad bypassed the town in favor of Medford, J’Ville’s population dwindled. Citizens in the 1960s recognized the town’s charms and petitioned to have it deemed a National Historic Landmark. Today, more than 100 buildings are officially registered—buildings that bear the original names of the residents like Beekman Bank. Décor at the Jacksonville Inn takes dinner guests back in time with walls lined in locally quarried sandstone, with flecks of gold still visible. Taste wine in town at South Stage Cellars or pick up a bottle and some treats at the Cheesemonger’s Wife. Photographer Peter Britt, Jacksonville’s most famous former resident, took the first successful photo of Crater Lake in 1874 and subsequent images were used in the campaign to create Crater Lake National Park in 1902. Today, the Britt Festival, held on the grounds of the Britt home, once again swells the town’s population each summer as music fans swarm to catch acts similar to the lineup at Chateau Ste. Michelle in Woodinville.

Applegate Valley Ag

Wine country rolls along Highway 238 through the Applegate Valley with notable producers like Spanish-varietal specialist Red Lily Vineyards situated on idyllic Chapman Creek, Valley View Winery named after the region’s first vineyard planted by Peter Britt, and Plaisance Ranch with a laid-back ranch-style tasting room (appropriate considering they also raise grass-fed organic beef cattle). But once you taste the delights awaiting you at Pennington Farms at Grants Pass, you might just forget all about wine tasting. In 1994, Joe Pennington faxed a photo of the property to his wife Kathy and immediately put an offer on it, moving their five kids out from Denver shortly thereafter. Joe specializes in Rubus fruit—sometimes called cane or bramble fruit. Well-known examples include raspberries, blackberries and hybrids like loganberries, tayberries and boysenberries. Over the years, Joe has planted 40 acres with hundreds of varieties. One of his favorites is the lusterberry—a cross between a boysenberry and a Cascade blackberry. Kathy transforms those berries into luscious jams and baked goods—her piecrust is second to none. The scent of butter hangs like a golden cloud over their kitchen, the Country Bakery, beckoning travelers to stay a while, have a bite to eat, swoon into a sweet buttery coma.

Getteth Thee to Ashland

Shakespeare is alive and well in the theaters of Ashland, home of the Oregon Shakespeare Festival featuring 11 plays and musicals throughout its 2017 February–October season. Ashland also has a thriving culinary scene thanks to the bounty of fresh produce grown in the region and the cultured tastes of its citizens. Farm-to-table is the name of the game at most eateries including the Peerless Restaurant, Luna Cafe & Mercantile and newcomer Lorella Ashland, helmed by chef Josh Dorcak, two-time-defending Ashland Culinary Festival champion. Adventure seekers should head to Mount Ashland. A skier’s haunt in the winter, the mountain beckons in summer months for mountain bikers, hikers and bird-watchers.  

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